JP5833392B2 - (トリフルオロビニル)ベンゼン類およびその製造方法 - Google Patents
(トリフルオロビニル)ベンゼン類およびその製造方法 Download PDFInfo
- Publication number
- JP5833392B2 JP5833392B2 JP2011202530A JP2011202530A JP5833392B2 JP 5833392 B2 JP5833392 B2 JP 5833392B2 JP 2011202530 A JP2011202530 A JP 2011202530A JP 2011202530 A JP2011202530 A JP 2011202530A JP 5833392 B2 JP5833392 B2 JP 5833392B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- group
- mmol
- bis
- palladium
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- SUTQSIHGGHVXFK-UHFFFAOYSA-N 1,2,2-trifluoroethenylbenzene Chemical class FC(F)=C(F)C1=CC=CC=C1 SUTQSIHGGHVXFK-UHFFFAOYSA-N 0.000 title claims description 21
- 238000000034 method Methods 0.000 title claims description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 110
- 238000006243 chemical reaction Methods 0.000 claims description 68
- 229910052763 palladium Inorganic materials 0.000 claims description 56
- -1 1,3,2-dioxaborolan-2-yl group Chemical group 0.000 claims description 55
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 35
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 32
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 claims description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- 238000004519 manufacturing process Methods 0.000 claims description 20
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 18
- FVFIICQSMOFGNU-UHFFFAOYSA-N (1,1-dichloro-4-diphenylphosphanylbutyl)-diphenylphosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C(Cl)(Cl)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 FVFIICQSMOFGNU-UHFFFAOYSA-N 0.000 claims description 17
- 239000003446 ligand Substances 0.000 claims description 16
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 16
- USVZFSNDGFNNJT-UHFFFAOYSA-N cyclopenta-1,4-dien-1-yl(diphenyl)phosphane (2,3-dichlorocyclopenta-1,4-dien-1-yl)-diphenylphosphane iron(2+) Chemical compound [Fe++].c1cc[c-](c1)P(c1ccccc1)c1ccccc1.Clc1c(cc[c-]1Cl)P(c1ccccc1)c1ccccc1 USVZFSNDGFNNJT-UHFFFAOYSA-N 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 claims description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical group [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- BCJVBDBJSMFBRW-UHFFFAOYSA-N 4-diphenylphosphanylbutyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCCP(C=1C=CC=CC=1)C1=CC=CC=C1 BCJVBDBJSMFBRW-UHFFFAOYSA-N 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 239000011698 potassium fluoride Substances 0.000 claims description 4
- 235000003270 potassium fluoride Nutrition 0.000 claims description 4
- UKSZBOKPHAQOMP-SVLSSHOZSA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 UKSZBOKPHAQOMP-SVLSSHOZSA-N 0.000 claims description 3
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 125000004442 acylamino group Chemical group 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000001626 borono group Chemical group [H]OB([*])O[H] 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- XPPWLXNXHSNMKC-UHFFFAOYSA-N phenylboron Chemical class [B]C1=CC=CC=C1 XPPWLXNXHSNMKC-UHFFFAOYSA-N 0.000 claims description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 112
- 229910052786 argon Inorganic materials 0.000 description 56
- 239000000203 mixture Substances 0.000 description 54
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 30
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 28
- 238000010898 silica gel chromatography Methods 0.000 description 27
- 239000000706 filtrate Substances 0.000 description 26
- 238000005160 1H NMR spectroscopy Methods 0.000 description 19
- 238000005481 NMR spectroscopy Methods 0.000 description 19
- 239000002253 acid Substances 0.000 description 12
- CTYCWWVGLTWOMT-UHFFFAOYSA-N 1-nitro-3-(1,2,2-trifluoroethenyl)benzene Chemical compound [O-][N+](=O)C1=CC=CC(C(F)=C(F)F)=C1 CTYCWWVGLTWOMT-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 8
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 8
- ZNRGSYUVFVNSAW-UHFFFAOYSA-N 3-nitrophenylboronic acid Chemical compound OB(O)C1=CC=CC([N+]([O-])=O)=C1 ZNRGSYUVFVNSAW-UHFFFAOYSA-N 0.000 description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- 238000006467 substitution reaction Methods 0.000 description 7
- JKJZYWLFVNOLAF-UHFFFAOYSA-N 1-phenyl-4-(1,2,2-trifluoroethenyl)benzene Chemical group C1=CC(C(F)=C(F)F)=CC=C1C1=CC=CC=C1 JKJZYWLFVNOLAF-UHFFFAOYSA-N 0.000 description 6
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 5
- 238000004817 gas chromatography Methods 0.000 description 5
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 5
- XPEIJWZLPWNNOK-UHFFFAOYSA-N (4-phenylphenyl)boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=CC=CC=C1 XPEIJWZLPWNNOK-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- CEBAHYWORUOILU-UHFFFAOYSA-N (4-cyanophenyl)boronic acid Chemical compound OB(O)C1=CC=C(C#N)C=C1 CEBAHYWORUOILU-UHFFFAOYSA-N 0.000 description 3
- SOKFEJKZYHYKSY-UHFFFAOYSA-N (4-propoxyphenyl)boronic acid Chemical compound CCCOC1=CC=C(B(O)O)C=C1 SOKFEJKZYHYKSY-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 125000003963 dichloro group Chemical group Cl* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000002940 palladium Chemical class 0.000 description 3
- 150000002941 palladium compounds Chemical class 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- ROEQGIFOWRQYHD-UHFFFAOYSA-N (2-methoxyphenyl)boronic acid Chemical compound COC1=CC=CC=C1B(O)O ROEQGIFOWRQYHD-UHFFFAOYSA-N 0.000 description 2
- NZNRMUVHUVCIBR-UHFFFAOYSA-N (3-fluoro-4-formylphenyl)boronic acid Chemical compound OB(O)C1=CC=C(C=O)C(F)=C1 NZNRMUVHUVCIBR-UHFFFAOYSA-N 0.000 description 2
- YJQDBKGGRPJSOI-UHFFFAOYSA-N (3-formyl-4-methoxyphenyl)boronic acid Chemical compound COC1=CC=C(B(O)O)C=C1C=O YJQDBKGGRPJSOI-UHFFFAOYSA-N 0.000 description 2
- TYKYVLDAFDKFHV-UHFFFAOYSA-N (3-formyl-5-propan-2-yloxyphenyl)boronic acid Chemical compound CC(C)OC1=CC(C=O)=CC(B(O)O)=C1 TYKYVLDAFDKFHV-UHFFFAOYSA-N 0.000 description 2
- NLLGFYPSWCMUIV-UHFFFAOYSA-N (3-methoxyphenyl)boronic acid Chemical compound COC1=CC=CC(B(O)O)=C1 NLLGFYPSWCMUIV-UHFFFAOYSA-N 0.000 description 2
- OBQRODBYVNIZJU-UHFFFAOYSA-N (4-acetylphenyl)boronic acid Chemical compound CC(=O)C1=CC=C(B(O)O)C=C1 OBQRODBYVNIZJU-UHFFFAOYSA-N 0.000 description 2
- CAYQIZIAYYNFCS-UHFFFAOYSA-N (4-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Cl)C=C1 CAYQIZIAYYNFCS-UHFFFAOYSA-N 0.000 description 2
- QWMJEUJXWVZSAG-UHFFFAOYSA-N (4-ethenylphenyl)boronic acid Chemical compound OB(O)C1=CC=C(C=C)C=C1 QWMJEUJXWVZSAG-UHFFFAOYSA-N 0.000 description 2
- RZCPLOMUUCFPQA-UHFFFAOYSA-N (4-ethylphenyl)boronic acid Chemical compound CCC1=CC=C(B(O)O)C=C1 RZCPLOMUUCFPQA-UHFFFAOYSA-N 0.000 description 2
- PQCXFUXRTRESBD-UHFFFAOYSA-N (4-methoxycarbonylphenyl)boronic acid Chemical compound COC(=O)C1=CC=C(B(O)O)C=C1 PQCXFUXRTRESBD-UHFFFAOYSA-N 0.000 description 2
- MNJYZNVROSZZQC-UHFFFAOYSA-N (4-tert-butylphenyl)boronic acid Chemical compound CC(C)(C)C1=CC=C(B(O)O)C=C1 MNJYZNVROSZZQC-UHFFFAOYSA-N 0.000 description 2
- LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-bis(diphenylphosphino)propane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 description 2
- SLIVAUDVBGNMSB-UHFFFAOYSA-N 1-methoxy-2-(1,2,2-trifluoroethenyl)benzene Chemical compound COC1=CC=CC=C1C(F)=C(F)F SLIVAUDVBGNMSB-UHFFFAOYSA-N 0.000 description 2
- XOKRPZXZYDIEQC-UHFFFAOYSA-N 1-methoxy-3-(1,2,2-trifluoroethenyl)benzene Chemical compound COC1=CC=CC(C(F)=C(F)F)=C1 XOKRPZXZYDIEQC-UHFFFAOYSA-N 0.000 description 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- VQFPNTRNUSBZKD-UHFFFAOYSA-N 3-propan-2-yloxy-5-(1,2,2-trifluoroethenyl)benzaldehyde Chemical compound C(C)(C)OC=1C=C(C=O)C=C(C1)C(=C(F)F)F VQFPNTRNUSBZKD-UHFFFAOYSA-N 0.000 description 2
- SSCUBFCYKADABN-UHFFFAOYSA-N 4-(1,2,2-trifluoroethenyl)benzonitrile Chemical compound FC(F)=C(F)C1=CC=C(C#N)C=C1 SSCUBFCYKADABN-UHFFFAOYSA-N 0.000 description 2
- 0 C*c1cc(OC)ccc1 Chemical compound C*c1cc(OC)ccc1 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 150000001642 boronic acid derivatives Chemical class 0.000 description 2
- 125000005620 boronic acid group Chemical class 0.000 description 2
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
- 229910000024 caesium carbonate Inorganic materials 0.000 description 2
- AMJQWGIYCROUQF-UHFFFAOYSA-N calcium;methanolate Chemical compound [Ca+2].[O-]C.[O-]C AMJQWGIYCROUQF-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- WDUDHEOUGWAKFD-UHFFFAOYSA-N ditert-butyl(cyclopenta-2,4-dien-1-yl)phosphane;iron(2+) Chemical compound [Fe+2].CC(C)(C)P(C(C)(C)C)C1=CC=C[CH-]1.CC(C)(C)P(C(C)(C)C)C1=CC=C[CH-]1 WDUDHEOUGWAKFD-UHFFFAOYSA-N 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- 239000004210 ether based solvent Substances 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 2
- 229910002094 inorganic tetrachloropalladate Inorganic materials 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000008204 material by function Substances 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 2
- HUMMCEUVDBVXTQ-UHFFFAOYSA-N naphthalen-1-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CC=CC2=C1 HUMMCEUVDBVXTQ-UHFFFAOYSA-N 0.000 description 2
- KPTRDYONBVUWPD-UHFFFAOYSA-N naphthalen-2-ylboronic acid Chemical compound C1=CC=CC2=CC(B(O)O)=CC=C21 KPTRDYONBVUWPD-UHFFFAOYSA-N 0.000 description 2
- KPSSIOMAKSHJJG-UHFFFAOYSA-N neopentyl alcohol Chemical compound CC(C)(C)CO KPSSIOMAKSHJJG-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 2
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000005920 sec-butoxy group Chemical group 0.000 description 2
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- YEHSEFMAODBQOR-UHFFFAOYSA-N (1-chloro-2,2-difluoroethenyl)benzene Chemical class FC(F)=C(Cl)C1=CC=CC=C1 YEHSEFMAODBQOR-UHFFFAOYSA-N 0.000 description 1
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 1
- UBKCMQCDHVYUAF-UHFFFAOYSA-N (2,2-dichloro-3-diphenylphosphanylpropyl)-diphenylphosphane Chemical compound ClC(CP(C1=CC=CC=C1)C1=CC=CC=C1)(CP(C1=CC=CC=C1)C1=CC=CC=C1)Cl UBKCMQCDHVYUAF-UHFFFAOYSA-N 0.000 description 1
- LDQLSQRFSNMANA-UHFFFAOYSA-N (2,3,4-trimethoxyphenyl)boronic acid Chemical compound COC1=CC=C(B(O)O)C(OC)=C1OC LDQLSQRFSNMANA-UHFFFAOYSA-N 0.000 description 1
- VREWSCMOGIXMDQ-UHFFFAOYSA-N (2,3-dimethoxyphenyl)boronic acid Chemical compound COC1=CC=CC(B(O)O)=C1OC VREWSCMOGIXMDQ-UHFFFAOYSA-N 0.000 description 1
- NNQHKSYWLLYOHI-UHFFFAOYSA-N (2,4,5-trimethylphenyl)boronic acid Chemical compound CC1=CC(C)=C(B(O)O)C=C1C NNQHKSYWLLYOHI-UHFFFAOYSA-N 0.000 description 1
- BZXQRXJJJUZZAJ-UHFFFAOYSA-N (2,4,6-trimethylphenyl)boronic acid Chemical compound CC1=CC(C)=C(B(O)O)C(C)=C1 BZXQRXJJJUZZAJ-UHFFFAOYSA-N 0.000 description 1
- QNEGDGPAXKYZHZ-UHFFFAOYSA-N (2,4-dichlorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Cl)C=C1Cl QNEGDGPAXKYZHZ-UHFFFAOYSA-N 0.000 description 1
- SQTUYFKNCCBFRR-UHFFFAOYSA-N (2,4-dimethoxyphenyl)boronic acid Chemical compound COC1=CC=C(B(O)O)C(OC)=C1 SQTUYFKNCCBFRR-UHFFFAOYSA-N 0.000 description 1
- QOZLFNQLIKOGDR-UHFFFAOYSA-N (2,5-dimethoxyphenyl)boronic acid Chemical compound COC1=CC=C(OC)C(B(O)O)=C1 QOZLFNQLIKOGDR-UHFFFAOYSA-N 0.000 description 1
- CXDPUSMFYPQXCV-UHFFFAOYSA-N (2,6-dichlorophenyl)boronic acid Chemical compound OB(O)C1=C(Cl)C=CC=C1Cl CXDPUSMFYPQXCV-UHFFFAOYSA-N 0.000 description 1
- BKWVXPCYDRURMK-UHFFFAOYSA-N (2,6-dimethoxyphenyl)boronic acid Chemical compound COC1=CC=CC(OC)=C1B(O)O BKWVXPCYDRURMK-UHFFFAOYSA-N 0.000 description 1
- UMOPBIVXPOETPG-UHFFFAOYSA-N (2-acetamidophenyl)boronic acid Chemical compound CC(=O)NC1=CC=CC=C1B(O)O UMOPBIVXPOETPG-UHFFFAOYSA-N 0.000 description 1
- ZKAOVABYLXQUTI-UHFFFAOYSA-N (2-acetylphenyl)boronic acid Chemical compound CC(=O)C1=CC=CC=C1B(O)O ZKAOVABYLXQUTI-UHFFFAOYSA-N 0.000 description 1
- NCHRUWKNTBNIBK-UHFFFAOYSA-N (2-amino-5-chlorophenyl)boronic acid Chemical compound NC1=CC=C(Cl)C=C1B(O)O NCHRUWKNTBNIBK-UHFFFAOYSA-N 0.000 description 1
- DIRRKLFMHQUJCM-UHFFFAOYSA-N (2-aminophenyl)boronic acid Chemical compound NC1=CC=CC=C1B(O)O DIRRKLFMHQUJCM-UHFFFAOYSA-N 0.000 description 1
- LOFURYXLNWGVFJ-UHFFFAOYSA-N (2-butan-2-yloxyphenyl)boronic acid Chemical compound CCC(C)OC1=CC=CC=C1B(O)O LOFURYXLNWGVFJ-UHFFFAOYSA-N 0.000 description 1
- MPGPVHMCNDIRLK-UHFFFAOYSA-N (2-butan-2-ylphenyl)boronic acid Chemical compound CCC(C)C1=CC=CC=C1B(O)O MPGPVHMCNDIRLK-UHFFFAOYSA-N 0.000 description 1
- NNZPYUBZXKOFHS-UHFFFAOYSA-N (2-butoxyphenyl)boronic acid Chemical compound CCCCOC1=CC=CC=C1B(O)O NNZPYUBZXKOFHS-UHFFFAOYSA-N 0.000 description 1
- FVYUDYMMTUEXCQ-UHFFFAOYSA-N (2-butylphenyl)boronic acid Chemical compound CCCCC1=CC=CC=C1B(O)O FVYUDYMMTUEXCQ-UHFFFAOYSA-N 0.000 description 1
- YNZXUVCJPQNYHR-UHFFFAOYSA-N (2-chloro-5-cyanophenyl)boronic acid Chemical compound OB(O)C1=CC(C#N)=CC=C1Cl YNZXUVCJPQNYHR-UHFFFAOYSA-N 0.000 description 1
- OAZJSBAREVKCCK-UHFFFAOYSA-N (2-chlorophenyl)boron Chemical compound [B]C1=CC=CC=C1Cl OAZJSBAREVKCCK-UHFFFAOYSA-N 0.000 description 1
- NPLZNDDFVCGRAG-UHFFFAOYSA-N (2-cyanophenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1C#N NPLZNDDFVCGRAG-UHFFFAOYSA-N 0.000 description 1
- QHFAXRHEKNHTDH-UHFFFAOYSA-N (2-ethenylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1C=C QHFAXRHEKNHTDH-UHFFFAOYSA-N 0.000 description 1
- QZKVVOXAEBCLPZ-UHFFFAOYSA-N (2-ethoxycarbonylphenyl)boronic acid Chemical compound CCOC(=O)C1=CC=CC=C1B(O)O QZKVVOXAEBCLPZ-UHFFFAOYSA-N 0.000 description 1
- DGFCTCGCMKEILT-UHFFFAOYSA-N (2-ethoxyphenyl)boronic acid Chemical compound CCOC1=CC=CC=C1B(O)O DGFCTCGCMKEILT-UHFFFAOYSA-N 0.000 description 1
- QSSPYZOSTJDTTL-UHFFFAOYSA-N (2-ethylphenyl)boronic acid Chemical compound CCC1=CC=CC=C1B(O)O QSSPYZOSTJDTTL-UHFFFAOYSA-N 0.000 description 1
- YJXJCPZHXDDRNH-UHFFFAOYSA-N (2-fluoro-3-formylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC(C=O)=C1F YJXJCPZHXDDRNH-UHFFFAOYSA-N 0.000 description 1
- OAEJODVYVOAOPH-UHFFFAOYSA-N (2-fluoro-4-formylphenyl)boronic acid Chemical compound OB(O)C1=CC=C(C=O)C=C1F OAEJODVYVOAOPH-UHFFFAOYSA-N 0.000 description 1
- ZSSNGMFKYFBOAG-UHFFFAOYSA-N (2-formyl-4-methoxyphenyl)boronic acid Chemical compound COC1=CC=C(B(O)O)C(C=O)=C1 ZSSNGMFKYFBOAG-UHFFFAOYSA-N 0.000 description 1
- JLGRMVFJTQAITE-UHFFFAOYSA-N (2-formyl-4-methylphenyl)boronic acid Chemical compound CC1=CC=C(B(O)O)C(C=O)=C1 JLGRMVFJTQAITE-UHFFFAOYSA-N 0.000 description 1
- YISYHZMNRATPRA-UHFFFAOYSA-N (2-formyl-5-methoxyphenyl)boronic acid Chemical compound COC1=CC=C(C=O)C(B(O)O)=C1 YISYHZMNRATPRA-UHFFFAOYSA-N 0.000 description 1
- MMKCZTKFYDEERR-UHFFFAOYSA-N (2-formyl-5-methylphenyl)boronic acid Chemical compound CC1=CC=C(C=O)C(B(O)O)=C1 MMKCZTKFYDEERR-UHFFFAOYSA-N 0.000 description 1
- DGUWACLYDSWXRZ-UHFFFAOYSA-N (2-formylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1C=O DGUWACLYDSWXRZ-UHFFFAOYSA-N 0.000 description 1
- LWNWZQJRSFHZRG-UHFFFAOYSA-N (2-methoxy-4-methylphenyl)boronic acid Chemical compound COC1=CC(C)=CC=C1B(O)O LWNWZQJRSFHZRG-UHFFFAOYSA-N 0.000 description 1
- ODAXNYMENLFYMY-UHFFFAOYSA-N (2-methoxycarbonylphenyl)boronic acid Chemical compound COC(=O)C1=CC=CC=C1B(O)O ODAXNYMENLFYMY-UHFFFAOYSA-N 0.000 description 1
- NSJVYHOPHZMZPN-UHFFFAOYSA-N (2-methylphenyl)boronic acid Chemical compound CC1=CC=CC=C1B(O)O NSJVYHOPHZMZPN-UHFFFAOYSA-N 0.000 description 1
- SFUIGUOONHIVLG-UHFFFAOYSA-N (2-nitrophenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1[N+]([O-])=O SFUIGUOONHIVLG-UHFFFAOYSA-N 0.000 description 1
- FPGITLXCVXWCNQ-UHFFFAOYSA-N (2-prop-1-en-2-ylphenyl)boronic acid Chemical compound CC(=C)C1=CC=CC=C1B(O)O FPGITLXCVXWCNQ-UHFFFAOYSA-N 0.000 description 1
- UHSGPEFNAZQASO-UHFFFAOYSA-N (2-propan-2-yloxycarbonylphenyl)boronic acid Chemical compound CC(C)OC(=O)C1=CC=CC=C1B(O)O UHSGPEFNAZQASO-UHFFFAOYSA-N 0.000 description 1
- KTZUVUWIBZMHMC-UHFFFAOYSA-N (2-propan-2-ylphenyl)boronic acid Chemical compound CC(C)C1=CC=CC=C1B(O)O KTZUVUWIBZMHMC-UHFFFAOYSA-N 0.000 description 1
- JJWUQVDDBBSDBY-UHFFFAOYSA-N (2-propanoylphenyl)boronic acid Chemical compound CCC(=O)C1=CC=CC=C1B(O)O JJWUQVDDBBSDBY-UHFFFAOYSA-N 0.000 description 1
- ZDPMWYOVDLDQDT-UHFFFAOYSA-N (2-propoxyphenyl)boronic acid Chemical compound CCCOC1=CC=CC=C1B(O)O ZDPMWYOVDLDQDT-UHFFFAOYSA-N 0.000 description 1
- OUZANECXUCYGEG-UHFFFAOYSA-N (2-propylphenyl)boronic acid Chemical compound CCCC1=CC=CC=C1B(O)O OUZANECXUCYGEG-UHFFFAOYSA-N 0.000 description 1
- AZFVMRWLGCYBFP-UHFFFAOYSA-N (2-silylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1[SiH3] AZFVMRWLGCYBFP-UHFFFAOYSA-N 0.000 description 1
- LXLMKMLQQJSOCB-UHFFFAOYSA-N (2-tert-butylphenyl)boronic acid Chemical compound CC(C)(C)C1=CC=CC=C1B(O)O LXLMKMLQQJSOCB-UHFFFAOYSA-N 0.000 description 1
- KIJPIBNIBJYCDG-UHFFFAOYSA-N (2-trimethylsilylphenyl)boronic acid Chemical compound C[Si](C)(C)C1=CC=CC=C1B(O)O KIJPIBNIBJYCDG-UHFFFAOYSA-N 0.000 description 1
- KEEKMOIRJUWKNK-CABZTGNLSA-N (2S)-2-[[2-[(4R)-4-(difluoromethyl)-2-oxo-1,3-thiazolidin-3-yl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]amino]propanamide Chemical compound FC([C@H]1N(C(SC1)=O)C=1N=C2N(CCOC3=C2C=CC(=C3)N[C@H](C(=O)N)C)C=1)F KEEKMOIRJUWKNK-CABZTGNLSA-N 0.000 description 1
- BIIBYWQGRFWQKM-JVVROLKMSA-N (2S)-N-[4-(cyclopropylamino)-3,4-dioxo-1-[(3S)-2-oxopyrrolidin-3-yl]butan-2-yl]-2-[[(E)-3-(2,4-dichlorophenyl)prop-2-enoyl]amino]-4,4-dimethylpentanamide Chemical compound CC(C)(C)C[C@@H](C(NC(C[C@H](CCN1)C1=O)C(C(NC1CC1)=O)=O)=O)NC(/C=C/C(C=CC(Cl)=C1)=C1Cl)=O BIIBYWQGRFWQKM-JVVROLKMSA-N 0.000 description 1
- JKIGHOARKAIPJI-UHFFFAOYSA-N (3,4-dichlorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Cl)C(Cl)=C1 JKIGHOARKAIPJI-UHFFFAOYSA-N 0.000 description 1
- RCVDPBFUMYUKPB-UHFFFAOYSA-N (3,4-dimethoxyphenyl)boronic acid Chemical compound COC1=CC=C(B(O)O)C=C1OC RCVDPBFUMYUKPB-UHFFFAOYSA-N 0.000 description 1
- DJGHSJBYKIQHIK-UHFFFAOYSA-N (3,5-dimethylphenyl)boronic acid Chemical compound CC1=CC(C)=CC(B(O)O)=C1 DJGHSJBYKIQHIK-UHFFFAOYSA-N 0.000 description 1
- RPCBIEHUQSGPNA-UHFFFAOYSA-N (3,5-ditert-butylphenyl)boronic acid Chemical compound CC(C)(C)C1=CC(B(O)O)=CC(C(C)(C)C)=C1 RPCBIEHUQSGPNA-UHFFFAOYSA-N 0.000 description 1
- IBTSWKLSEOGJGJ-UHFFFAOYSA-N (3-acetamidophenyl)boronic acid Chemical compound CC(=O)NC1=CC=CC(B(O)O)=C1 IBTSWKLSEOGJGJ-UHFFFAOYSA-N 0.000 description 1
- LZUCQFAALCRNCA-UHFFFAOYSA-N (3-but-1-enylphenyl)boronic acid Chemical compound CCC=CC1=CC=CC(B(O)O)=C1 LZUCQFAALCRNCA-UHFFFAOYSA-N 0.000 description 1
- UKHFDAQDNBNPSM-UHFFFAOYSA-N (3-butan-2-yloxyphenyl)boronic acid Chemical compound CCC(C)OC1=CC=CC(B(O)O)=C1 UKHFDAQDNBNPSM-UHFFFAOYSA-N 0.000 description 1
- QZWFUFQWGUVPPT-UHFFFAOYSA-N (3-butan-2-ylphenyl)boronic acid Chemical compound CCC(C)C1=CC=CC(B(O)O)=C1 QZWFUFQWGUVPPT-UHFFFAOYSA-N 0.000 description 1
- HMAUOFNDSAIVHG-UHFFFAOYSA-N (3-butanoylphenyl)boronic acid Chemical compound CCCC(=O)C1=CC=CC(B(O)O)=C1 HMAUOFNDSAIVHG-UHFFFAOYSA-N 0.000 description 1
- OXIDCSRUHBZBQG-UHFFFAOYSA-N (3-butoxy-5-formylphenyl)boronic acid Chemical compound CCCCOC1=CC(C=O)=CC(B(O)O)=C1 OXIDCSRUHBZBQG-UHFFFAOYSA-N 0.000 description 1
- ZTRKYYYDXARQRD-UHFFFAOYSA-N (3-butoxyphenyl)boronic acid Chemical compound CCCCOC1=CC=CC(B(O)O)=C1 ZTRKYYYDXARQRD-UHFFFAOYSA-N 0.000 description 1
- NTSZBZIBMNMDKQ-UHFFFAOYSA-N (3-butylphenyl)boronic acid Chemical compound CCCCC1=CC=CC(B(O)O)=C1 NTSZBZIBMNMDKQ-UHFFFAOYSA-N 0.000 description 1
- FMEZHQZTXJATTF-UHFFFAOYSA-N (3-chloro-4,5-dimethoxyphenyl)boronic acid Chemical compound COC1=CC(B(O)O)=CC(Cl)=C1OC FMEZHQZTXJATTF-UHFFFAOYSA-N 0.000 description 1
- DJOMWLVGTUQULT-UHFFFAOYSA-N (3-chloro-4-methoxycarbonylphenyl)boronic acid Chemical compound COC(=O)C1=CC=C(B(O)O)C=C1Cl DJOMWLVGTUQULT-UHFFFAOYSA-N 0.000 description 1
- VUTJHOWRPUPHIG-UHFFFAOYSA-N (3-chloro-4-methoxyphenyl)boronic acid Chemical compound COC1=CC=C(B(O)O)C=C1Cl VUTJHOWRPUPHIG-UHFFFAOYSA-N 0.000 description 1
- YTJUYWRCAZWVSX-UHFFFAOYSA-N (3-chloro-4-methylphenyl)boronic acid Chemical compound CC1=CC=C(B(O)O)C=C1Cl YTJUYWRCAZWVSX-UHFFFAOYSA-N 0.000 description 1
- SDEAGACSNFSZCU-UHFFFAOYSA-N (3-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=CC(Cl)=C1 SDEAGACSNFSZCU-UHFFFAOYSA-N 0.000 description 1
- XDBHWPLGGBLUHH-UHFFFAOYSA-N (3-cyanophenyl)boronic acid Chemical compound OB(O)C1=CC=CC(C#N)=C1 XDBHWPLGGBLUHH-UHFFFAOYSA-N 0.000 description 1
- SYBQEKBVWDPVJM-UHFFFAOYSA-N (3-ethenylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC(C=C)=C1 SYBQEKBVWDPVJM-UHFFFAOYSA-N 0.000 description 1
- REHVCPNQQBDOJJ-UHFFFAOYSA-N (3-ethoxycarbonylphenyl)boronic acid Chemical compound CCOC(=O)C1=CC=CC(B(O)O)=C1 REHVCPNQQBDOJJ-UHFFFAOYSA-N 0.000 description 1
- CHCWUTJYLUBETR-UHFFFAOYSA-N (3-ethoxyphenyl)boronic acid Chemical compound CCOC1=CC=CC(B(O)O)=C1 CHCWUTJYLUBETR-UHFFFAOYSA-N 0.000 description 1
- CUHGCQVNNDUJCQ-UHFFFAOYSA-N (3-ethyl-4-formylphenyl)boronic acid Chemical compound CCC1=CC(B(O)O)=CC=C1C=O CUHGCQVNNDUJCQ-UHFFFAOYSA-N 0.000 description 1
- JIMVRUCDZGFJRE-UHFFFAOYSA-N (3-ethylphenyl)boronic acid Chemical compound CCC1=CC=CC(B(O)O)=C1 JIMVRUCDZGFJRE-UHFFFAOYSA-N 0.000 description 1
- LAQDUOXSWHKHBB-UHFFFAOYSA-N (3-fluoro-5-formylphenyl)boronic acid Chemical compound OB(O)C1=CC(F)=CC(C=O)=C1 LAQDUOXSWHKHBB-UHFFFAOYSA-N 0.000 description 1
- UHPDMPNTUUASKT-UHFFFAOYSA-N (3-formyl-4-methylphenyl)boronic acid Chemical compound CC1=CC=C(B(O)O)C=C1C=O UHPDMPNTUUASKT-UHFFFAOYSA-N 0.000 description 1
- BQBPIMVLGXGJIY-UHFFFAOYSA-N (3-formyl-5-methoxyphenyl)boronic acid Chemical compound COC1=CC(C=O)=CC(B(O)O)=C1 BQBPIMVLGXGJIY-UHFFFAOYSA-N 0.000 description 1
- IDXLUNCVVBZUEN-UHFFFAOYSA-N (3-formyl-5-methylphenyl)boronic acid Chemical compound CC1=CC(C=O)=CC(B(O)O)=C1 IDXLUNCVVBZUEN-UHFFFAOYSA-N 0.000 description 1
- MPQVVDQADAGQCM-UHFFFAOYSA-N (3-formyl-5-propoxyphenyl)boronic acid Chemical compound CCCOC1=CC(C=O)=CC(B(O)O)=C1 MPQVVDQADAGQCM-UHFFFAOYSA-N 0.000 description 1
- HJBGZJMKTOMQRR-UHFFFAOYSA-N (3-formylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC(C=O)=C1 HJBGZJMKTOMQRR-UHFFFAOYSA-N 0.000 description 1
- YCXPWNGIPLGCOJ-UHFFFAOYSA-N (3-methoxy-4-methoxycarbonylphenyl)boronic acid Chemical compound COC(=O)C1=CC=C(B(O)O)C=C1OC YCXPWNGIPLGCOJ-UHFFFAOYSA-N 0.000 description 1
- UMGAGEBOUIODFE-UHFFFAOYSA-N (3-methoxy-4-methylphenyl)boronic acid Chemical compound COC1=CC(B(O)O)=CC=C1C UMGAGEBOUIODFE-UHFFFAOYSA-N 0.000 description 1
- ZHDWUWYCLBTNBQ-UHFFFAOYSA-N (3-methoxycarbonyl-2-nitrophenyl)boronic acid Chemical compound COC(=O)C1=CC=CC(B(O)O)=C1[N+]([O-])=O ZHDWUWYCLBTNBQ-UHFFFAOYSA-N 0.000 description 1
- CDGIRLKQNJXHBJ-UHFFFAOYSA-N (3-methoxycarbonyl-5-nitrophenyl)boronic acid Chemical compound COC(=O)C1=CC(B(O)O)=CC([N+]([O-])=O)=C1 CDGIRLKQNJXHBJ-UHFFFAOYSA-N 0.000 description 1
- ALTLCJHSJMGSLT-UHFFFAOYSA-N (3-methoxycarbonylphenyl)boronic acid Chemical compound COC(=O)C1=CC=CC(B(O)O)=C1 ALTLCJHSJMGSLT-UHFFFAOYSA-N 0.000 description 1
- BJQCPCFFYBKRLM-UHFFFAOYSA-N (3-methylphenyl)boronic acid Chemical compound CC1=CC=CC(B(O)O)=C1 BJQCPCFFYBKRLM-UHFFFAOYSA-N 0.000 description 1
- KPHBNHAMRUACMR-UHFFFAOYSA-N (3-pentanoylphenyl)boronic acid Chemical compound CCCCC(=O)C1=CC=CC(B(O)O)=C1 KPHBNHAMRUACMR-UHFFFAOYSA-N 0.000 description 1
- GOXICVKOZJFRMB-UHFFFAOYSA-N (3-phenylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC(C=2C=CC=CC=2)=C1 GOXICVKOZJFRMB-UHFFFAOYSA-N 0.000 description 1
- HXVODQWMURGQMP-UHFFFAOYSA-N (3-propan-2-yloxycarbonylphenyl)boronic acid Chemical compound CC(C)OC(=O)C1=CC=CC(B(O)O)=C1 HXVODQWMURGQMP-UHFFFAOYSA-N 0.000 description 1
- QSWLFBMVIGQONC-UHFFFAOYSA-N (3-propan-2-ylphenyl)boronic acid Chemical compound CC(C)C1=CC=CC(B(O)O)=C1 QSWLFBMVIGQONC-UHFFFAOYSA-N 0.000 description 1
- HNEGUQPUGHVSEQ-UHFFFAOYSA-N (3-propanoylphenyl)boronic acid Chemical compound CCC(=O)C1=CC=CC(B(O)O)=C1 HNEGUQPUGHVSEQ-UHFFFAOYSA-N 0.000 description 1
- BSCFVVVAJINDLA-UHFFFAOYSA-N (3-propoxycarbonylphenyl)boronic acid Chemical compound CCCOC(=O)C1=CC=CC(B(O)O)=C1 BSCFVVVAJINDLA-UHFFFAOYSA-N 0.000 description 1
- SRSWMXFANVKOFH-UHFFFAOYSA-N (3-propoxyphenyl)boronic acid Chemical compound CCCOC1=CC=CC(B(O)O)=C1 SRSWMXFANVKOFH-UHFFFAOYSA-N 0.000 description 1
- TUDXWKSKLOPZSP-UHFFFAOYSA-N (3-propylphenyl)boronic acid Chemical compound CCCC1=CC=CC(B(O)O)=C1 TUDXWKSKLOPZSP-UHFFFAOYSA-N 0.000 description 1
- OKBOGYOXEDEGOG-UHFFFAOYSA-N (3-tert-butylphenyl)boronic acid Chemical compound CC(C)(C)C1=CC=CC(B(O)O)=C1 OKBOGYOXEDEGOG-UHFFFAOYSA-N 0.000 description 1
- QIVUCLWGARAQIO-OLIXTKCUSA-N (3s)-n-[(3s,5s,6r)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-yl]-2-oxospiro[1h-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-carboxamide Chemical compound C1([C@H]2[C@H](N(C(=O)[C@@H](NC(=O)C=3C=C4C[C@]5(CC4=NC=3)C3=CC=CN=C3NC5=O)C2)CC(F)(F)F)C)=C(F)C=CC(F)=C1F QIVUCLWGARAQIO-OLIXTKCUSA-N 0.000 description 1
- NYNZQNWKBKUAII-KBXCAEBGSA-N (3s)-n-[5-[(2r)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-3-yl]-3-hydroxypyrrolidine-1-carboxamide Chemical compound C1[C@@H](O)CCN1C(=O)NC1=C2N=C(N3[C@H](CCC3)C=3C(=CC=C(F)C=3)F)C=CN2N=C1 NYNZQNWKBKUAII-KBXCAEBGSA-N 0.000 description 1
- VYEWTHXZHHATTA-UHFFFAOYSA-N (4-acetamidophenyl)boronic acid Chemical compound CC(=O)NC1=CC=C(B(O)O)C=C1 VYEWTHXZHHATTA-UHFFFAOYSA-N 0.000 description 1
- CBHFQROGRLFSMS-UHFFFAOYSA-N (4-amino-3-methoxyphenyl)boronic acid Chemical compound COC1=CC(B(O)O)=CC=C1N CBHFQROGRLFSMS-UHFFFAOYSA-N 0.000 description 1
- IRTXQNNJQZNKRP-UHFFFAOYSA-N (4-amino-3-nitrophenyl)boronic acid Chemical compound NC1=CC=C(B(O)O)C=C1[N+]([O-])=O IRTXQNNJQZNKRP-UHFFFAOYSA-N 0.000 description 1
- NCNLNVWVRXJARW-UHFFFAOYSA-N (4-butan-2-yloxyphenyl)boronic acid Chemical compound CCC(C)OC1=CC=C(B(O)O)C=C1 NCNLNVWVRXJARW-UHFFFAOYSA-N 0.000 description 1
- CHSPURIZKQPJNH-UHFFFAOYSA-N (4-butan-2-ylphenyl)boronic acid Chemical compound CCC(C)C1=CC=C(B(O)O)C=C1 CHSPURIZKQPJNH-UHFFFAOYSA-N 0.000 description 1
- IGYWRXHZSLSNLZ-UHFFFAOYSA-N (4-butanoylphenyl)boronic acid Chemical compound CCCC(=O)C1=CC=C(B(O)O)C=C1 IGYWRXHZSLSNLZ-UHFFFAOYSA-N 0.000 description 1
- HDEKORLJQNHWOH-UHFFFAOYSA-N (4-butoxy-2-formylphenyl)boronic acid Chemical compound CCCCOC1=CC=C(B(O)O)C(C=O)=C1 HDEKORLJQNHWOH-UHFFFAOYSA-N 0.000 description 1
- CXMOGUFQKZWEGE-UHFFFAOYSA-N (4-butoxy-3-formylphenyl)boronic acid Chemical compound CCCCOC1=CC=C(B(O)O)C=C1C=O CXMOGUFQKZWEGE-UHFFFAOYSA-N 0.000 description 1
- QUPFQMXWFNJUNJ-UHFFFAOYSA-N (4-butoxyphenyl)boronic acid Chemical compound CCCCOC1=CC=C(B(O)O)C=C1 QUPFQMXWFNJUNJ-UHFFFAOYSA-N 0.000 description 1
- UGZUUTHZEATQAM-UHFFFAOYSA-N (4-butylphenyl)boronic acid Chemical compound CCCCC1=CC=C(B(O)O)C=C1 UGZUUTHZEATQAM-UHFFFAOYSA-N 0.000 description 1
- SRXXSLUUAWHGBZ-UHFFFAOYSA-N (4-chloro-2-methylphenyl)boronic acid Chemical compound CC1=CC(Cl)=CC=C1B(O)O SRXXSLUUAWHGBZ-UHFFFAOYSA-N 0.000 description 1
- UZDPQDBLCJDUAX-UHFFFAOYSA-N (4-chloro-3-methylphenyl)boronic acid Chemical compound CC1=CC(B(O)O)=CC=C1Cl UZDPQDBLCJDUAX-UHFFFAOYSA-N 0.000 description 1
- OBKSFBWOZSQGGC-UHFFFAOYSA-N (4-ethoxy-2,3-difluorophenyl)boronic acid Chemical compound CCOC1=CC=C(B(O)O)C(F)=C1F OBKSFBWOZSQGGC-UHFFFAOYSA-N 0.000 description 1
- MVOXIKZEUMPIGS-UHFFFAOYSA-N (4-ethoxy-2-formylphenyl)boronic acid Chemical compound CCOC1=CC=C(B(O)O)C(C=O)=C1 MVOXIKZEUMPIGS-UHFFFAOYSA-N 0.000 description 1
- ODRRAKCLFURNFU-UHFFFAOYSA-N (4-ethoxy-3-formylphenyl)boronic acid Chemical compound CCOC1=CC=C(B(O)O)C=C1C=O ODRRAKCLFURNFU-UHFFFAOYSA-N 0.000 description 1
- WRQNDLDUNQMTCL-UHFFFAOYSA-N (4-ethoxyphenyl)boronic acid Chemical compound CCOC1=CC=C(B(O)O)C=C1 WRQNDLDUNQMTCL-UHFFFAOYSA-N 0.000 description 1
- VXWBQOJISHAKKM-UHFFFAOYSA-N (4-formylphenyl)boronic acid Chemical compound OB(O)C1=CC=C(C=O)C=C1 VXWBQOJISHAKKM-UHFFFAOYSA-N 0.000 description 1
- WZUCSPWZHRVOSD-UHFFFAOYSA-N (4-methoxy-3,5-dimethylphenyl)boronic acid Chemical compound COC1=C(C)C=C(B(O)O)C=C1C WZUCSPWZHRVOSD-UHFFFAOYSA-N 0.000 description 1
- HAQVJQNWHRUPBH-UHFFFAOYSA-N (4-methoxy-3-nitrophenyl)boronic acid Chemical compound COC1=CC=C(B(O)O)C=C1[N+]([O-])=O HAQVJQNWHRUPBH-UHFFFAOYSA-N 0.000 description 1
- VOAAEKKFGLPLLU-UHFFFAOYSA-N (4-methoxyphenyl)boronic acid Chemical compound COC1=CC=C(B(O)O)C=C1 VOAAEKKFGLPLLU-UHFFFAOYSA-N 0.000 description 1
- BIWQNIMLAISTBV-UHFFFAOYSA-N (4-methylphenyl)boronic acid Chemical compound CC1=CC=C(B(O)O)C=C1 BIWQNIMLAISTBV-UHFFFAOYSA-N 0.000 description 1
- YUKJVXQLTQHPOR-UHFFFAOYSA-N (4-pentanoylphenyl)boronic acid Chemical compound CCCCC(=O)C1=CC=C(B(O)O)C=C1 YUKJVXQLTQHPOR-UHFFFAOYSA-N 0.000 description 1
- NEAHYDZVLVCOBB-UHFFFAOYSA-N (4-prop-1-enylphenyl)boronic acid Chemical compound CC=CC1=CC=C(B(O)O)C=C1 NEAHYDZVLVCOBB-UHFFFAOYSA-N 0.000 description 1
- IAEUFBDMVKQCLU-UHFFFAOYSA-N (4-propan-2-ylphenyl)boronic acid Chemical compound CC(C)C1=CC=C(B(O)O)C=C1 IAEUFBDMVKQCLU-UHFFFAOYSA-N 0.000 description 1
- SUXBGJJJOLDLKL-UHFFFAOYSA-N (4-propanoylphenyl)boronic acid Chemical compound CCC(=O)C1=CC=C(B(O)O)C=C1 SUXBGJJJOLDLKL-UHFFFAOYSA-N 0.000 description 1
- XJEONFAJOXSZDX-UHFFFAOYSA-N (4-propoxycarbonylphenyl)boronic acid Chemical compound CCCOC(=O)C1=CC=C(B(O)O)C=C1 XJEONFAJOXSZDX-UHFFFAOYSA-N 0.000 description 1
- WLCGYIWOKVWFLB-UHFFFAOYSA-N (4-propylphenyl)boronic acid Chemical compound CCCC1=CC=C(B(O)O)C=C1 WLCGYIWOKVWFLB-UHFFFAOYSA-N 0.000 description 1
- WZXOCGHYGPWDRF-UHFFFAOYSA-N (5-ethoxy-2-formylphenyl)boronic acid Chemical compound CCOC1=CC=C(C=O)C(B(O)O)=C1 WZXOCGHYGPWDRF-UHFFFAOYSA-N 0.000 description 1
- WJSQSAYFBOLNMO-UHFFFAOYSA-N (5-tert-butyl-2-formylphenyl)boronic acid Chemical compound CC(C)(C)C1=CC=C(C=O)C(B(O)O)=C1 WJSQSAYFBOLNMO-UHFFFAOYSA-N 0.000 description 1
- WIKBZUXHNPONPP-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-iodo-2-(trifluoromethyl)propane Chemical compound FC(F)(F)C(I)(C(F)(F)F)C(F)(F)F WIKBZUXHNPONPP-UHFFFAOYSA-N 0.000 description 1
- XGCDBGRZEKYHNV-UHFFFAOYSA-N 1,1-bis(diphenylphosphino)methane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CP(C=1C=CC=CC=1)C1=CC=CC=C1 XGCDBGRZEKYHNV-UHFFFAOYSA-N 0.000 description 1
- QFMZQPDHXULLKC-UHFFFAOYSA-N 1,2-bis(diphenylphosphino)ethane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 QFMZQPDHXULLKC-UHFFFAOYSA-N 0.000 description 1
- FLXPCPOVRUQHDM-UHFFFAOYSA-N 1-(1,2,2-trifluoroethenyl)naphthalene Chemical compound C1=CC=C2C(C(F)=C(F)F)=CC=CC2=C1 FLXPCPOVRUQHDM-UHFFFAOYSA-N 0.000 description 1
- ZSKXYSCQDWAUCM-UHFFFAOYSA-N 1-(chloromethyl)-2-dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1CCl ZSKXYSCQDWAUCM-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- RKJZTYSOGLWJGQ-UHFFFAOYSA-N 1-chloro-4-(1,2,2-trifluoroethenyl)benzene Chemical compound FC(F)=C(F)C1=CC=C(Cl)C=C1 RKJZTYSOGLWJGQ-UHFFFAOYSA-N 0.000 description 1
- XLHCHRQMZJSEIQ-UHFFFAOYSA-N 1-ethenyl-4-(1,2,2-trifluoroethenyl)benzene Chemical compound FC(F)=C(F)C1=CC=C(C=C)C=C1 XLHCHRQMZJSEIQ-UHFFFAOYSA-N 0.000 description 1
- YCZLOYMURBROBC-UHFFFAOYSA-N 1-ethyl-4-(1,2,2-trifluoroethenyl)benzene Chemical compound CCC1=CC=C(C(F)=C(F)F)C=C1 YCZLOYMURBROBC-UHFFFAOYSA-N 0.000 description 1
- 125000006019 1-methyl-1-propenyl group Chemical group 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- PUNPSXUEAQALMS-UHFFFAOYSA-N 1-tert-butyl-4-(1,2,2-trifluoroethenyl)benzene Chemical compound CC(C)(C)C1=CC=C(C(F)=C(F)F)C=C1 PUNPSXUEAQALMS-UHFFFAOYSA-N 0.000 description 1
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
- KJUCPVIVNLPLEE-UHFFFAOYSA-N 2,6-difluoro-n-[2-fluoro-5-[5-[2-[(6-morpholin-4-ylpyridin-3-yl)amino]pyrimidin-4-yl]-2-propan-2-yl-1,3-thiazol-4-yl]phenyl]benzenesulfonamide Chemical compound S1C(C(C)C)=NC(C=2C=C(NS(=O)(=O)C=3C(=CC=CC=3F)F)C(F)=CC=2)=C1C(N=1)=CC=NC=1NC(C=N1)=CC=C1N1CCOCC1 KJUCPVIVNLPLEE-UHFFFAOYSA-N 0.000 description 1
- BWLJVZFWCAKXFE-UHFFFAOYSA-N 2-(1,2,2-trifluoroethenyl)naphthalene Chemical compound C1=CC=CC2=CC(C(F)=C(F)F)=CC=C21 BWLJVZFWCAKXFE-UHFFFAOYSA-N 0.000 description 1
- OFUMROLKEGKJMS-UHFFFAOYSA-N 2-[2-(1,3-benzodioxol-5-yl)-3-[2-(cyclohexylamino)pyrimidin-4-yl]imidazol-4-yl]acetonitrile Chemical compound O1COC2=C1C=CC(=C2)C=1N(C(=CN=1)CC#N)C1=NC(=NC=C1)NC1CCCCC1 OFUMROLKEGKJMS-UHFFFAOYSA-N 0.000 description 1
- SSORSZACHCNXSJ-UHFFFAOYSA-N 2-[2-(3,4-dichlorophenyl)-3-[2-(2-hydroxypropylamino)pyrimidin-4-yl]imidazol-4-yl]acetonitrile Chemical compound ClC=1C=C(C=CC=1Cl)C=1N(C(=CN=1)CC#N)C1=NC(=NC=C1)NCC(C)O SSORSZACHCNXSJ-UHFFFAOYSA-N 0.000 description 1
- DILISPNYIVRDBP-UHFFFAOYSA-N 2-[3-[2-(2-hydroxypropylamino)pyrimidin-4-yl]-2-naphthalen-2-ylimidazol-4-yl]acetonitrile Chemical compound OC(CNC1=NC=CC(=N1)N1C(=NC=C1CC#N)C1=CC2=CC=CC=C2C=C1)C DILISPNYIVRDBP-UHFFFAOYSA-N 0.000 description 1
- DWKNOLCXIFYNFV-HSZRJFAPSA-N 2-[[(2r)-1-[1-[(4-chloro-3-methylphenyl)methyl]piperidin-4-yl]-5-oxopyrrolidine-2-carbonyl]amino]-n,n,6-trimethylpyridine-4-carboxamide Chemical compound CN(C)C(=O)C1=CC(C)=NC(NC(=O)[C@@H]2N(C(=O)CC2)C2CCN(CC=3C=C(C)C(Cl)=CC=3)CC2)=C1 DWKNOLCXIFYNFV-HSZRJFAPSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- LDJXFZUGZASGIW-UHFFFAOYSA-L 2-diphenylphosphanylethyl(diphenyl)phosphane;palladium(2+);dichloride Chemical compound Cl[Pd]Cl.C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 LDJXFZUGZASGIW-UHFFFAOYSA-L 0.000 description 1
- UCSOWOLMQGDTMQ-UHFFFAOYSA-N 2-fluoro-4-(1,2,2-trifluoroethenyl)benzaldehyde Chemical compound FC(F)=C(F)c1ccc(C=O)c(F)c1 UCSOWOLMQGDTMQ-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- JHUUPUMBZGWODW-UHFFFAOYSA-N 3,6-dihydro-1,2-dioxine Chemical compound C1OOCC=C1 JHUUPUMBZGWODW-UHFFFAOYSA-N 0.000 description 1
- BVGDAZBTIVRTGO-UONOGXRCSA-N 3-[(1r)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-[4-methoxy-6-[(2s)-2-methylpiperazin-1-yl]pyridin-3-yl]pyridin-2-amine Chemical compound C1([C@@H](C)OC=2C(N)=NC=C(C=2)C2=CN=C(C=C2OC)N2[C@H](CNCC2)C)=C(Cl)C=CC(F)=C1Cl BVGDAZBTIVRTGO-UONOGXRCSA-N 0.000 description 1
- SJGGDZCTGBKBCK-UHFFFAOYSA-N 3-acetylphenylboronic acid Chemical compound CC(=O)C1=CC=CC(B(O)O)=C1 SJGGDZCTGBKBCK-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- REDKQKNJWVIPIO-UHFFFAOYSA-N 4,4,5,5-tetramethyl-2-(4-phenylphenyl)-1,3,2-dioxaborolane Chemical group O1C(C)(C)C(C)(C)OB1C1=CC=C(C=2C=CC=CC=2)C=C1 REDKQKNJWVIPIO-UHFFFAOYSA-N 0.000 description 1
- UXHQLGLGLZKHTC-CUNXSJBXSA-N 4-[(3s,3ar)-3-cyclopentyl-7-(4-hydroxypiperidine-1-carbonyl)-3,3a,4,5-tetrahydropyrazolo[3,4-f]quinolin-2-yl]-2-chlorobenzonitrile Chemical compound C1CC(O)CCN1C(=O)C1=CC=C(C=2[C@@H]([C@H](C3CCCC3)N(N=2)C=2C=C(Cl)C(C#N)=CC=2)CC2)C2=N1 UXHQLGLGLZKHTC-CUNXSJBXSA-N 0.000 description 1
- YDDJRASPLUZILE-UHFFFAOYSA-N 5,5-dimethyl-2-(4-phenylphenyl)-1,3,2-dioxaborinane Chemical group O1CC(C)(C)COB1C1=CC=C(C=2C=CC=CC=2)C=C1 YDDJRASPLUZILE-UHFFFAOYSA-N 0.000 description 1
- RSIWALKZYXPAGW-NSHDSACASA-N 6-(3-fluorophenyl)-3-methyl-7-[(1s)-1-(7h-purin-6-ylamino)ethyl]-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound C=1([C@@H](NC=2C=3N=CNC=3N=CN=2)C)N=C2SC=C(C)N2C(=O)C=1C1=CC=CC(F)=C1 RSIWALKZYXPAGW-NSHDSACASA-N 0.000 description 1
- SJVGFKBLUYAEOK-SFHVURJKSA-N 6-[4-[(3S)-3-(3,5-difluorophenyl)-3,4-dihydropyrazole-2-carbonyl]piperidin-1-yl]pyrimidine-4-carbonitrile Chemical compound FC=1C=C(C=C(C=1)F)[C@@H]1CC=NN1C(=O)C1CCN(CC1)C1=CC(=NC=N1)C#N SJVGFKBLUYAEOK-SFHVURJKSA-N 0.000 description 1
- ONPGOSVDVDPBCY-CQSZACIVSA-N 6-amino-5-[(1r)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-n-[4-(4-methylpiperazine-1-carbonyl)phenyl]pyridazine-3-carboxamide Chemical compound O([C@H](C)C=1C(=C(F)C=CC=1Cl)Cl)C(C(=NN=1)N)=CC=1C(=O)NC(C=C1)=CC=C1C(=O)N1CCN(C)CC1 ONPGOSVDVDPBCY-CQSZACIVSA-N 0.000 description 1
- BWJHJLINOYAPEG-HOTGVXAUSA-N 8-chloro-6-[(6-chloropyridin-3-yl)methyl]-3-[(1S,2S)-2-hydroxycyclopentyl]-7-methyl-2H-1,3-benzoxazin-4-one Chemical compound ClC1=C(C(=CC=2C(N(COC=21)[C@@H]1[C@H](CCC1)O)=O)CC=1C=NC(=CC=1)Cl)C BWJHJLINOYAPEG-HOTGVXAUSA-N 0.000 description 1
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- RWXYROJZUBPJAD-UHFFFAOYSA-N B(C1=C(C=C(C=C1)C(=O)C)Cl)(O)O Chemical compound B(C1=C(C=C(C=C1)C(=O)C)Cl)(O)O RWXYROJZUBPJAD-UHFFFAOYSA-N 0.000 description 1
- BFTDZSDKJRIYIY-UHFFFAOYSA-N B(C1=C(C=C(C=C1)C(C)(C)C)C=O)(O)O Chemical compound B(C1=C(C=C(C=C1)C(C)(C)C)C=O)(O)O BFTDZSDKJRIYIY-UHFFFAOYSA-N 0.000 description 1
- AGNUZGFZQZASBW-UHFFFAOYSA-N B(C1=C(C=C(C=C1)C(C)CC)C=O)(O)O Chemical compound B(C1=C(C=C(C=C1)C(C)CC)C=O)(O)O AGNUZGFZQZASBW-UHFFFAOYSA-N 0.000 description 1
- XUBBJWUYLJJCJB-UHFFFAOYSA-N B(C1=C(C=C(C=C1)CC(C)C)C=O)(O)O Chemical compound B(C1=C(C=C(C=C1)CC(C)C)C=O)(O)O XUBBJWUYLJJCJB-UHFFFAOYSA-N 0.000 description 1
- GVSQXFKQBBCEQY-UHFFFAOYSA-N B(C1=C(C=C(C=C1)CC)C=O)(O)O Chemical compound B(C1=C(C=C(C=C1)CC)C=O)(O)O GVSQXFKQBBCEQY-UHFFFAOYSA-N 0.000 description 1
- YNWBTKPVSGIPRV-UHFFFAOYSA-N B(C1=C(C=C(C=C1)CCC)C=O)(O)O Chemical compound B(C1=C(C=C(C=C1)CCC)C=O)(O)O YNWBTKPVSGIPRV-UHFFFAOYSA-N 0.000 description 1
- POQPRSZMSIVBHX-UHFFFAOYSA-N B(C1=C(C=C(C=C1)CCCC)C=O)(O)O Chemical compound B(C1=C(C=C(C=C1)CCCC)C=O)(O)O POQPRSZMSIVBHX-UHFFFAOYSA-N 0.000 description 1
- ZHNZLROKVQSTSU-UHFFFAOYSA-N B(C1=C(C=C(C=C1)OC(C)(C)C)C=O)(O)O Chemical compound B(C1=C(C=C(C=C1)OC(C)(C)C)C=O)(O)O ZHNZLROKVQSTSU-UHFFFAOYSA-N 0.000 description 1
- MWVUQGFFVPEIDF-UHFFFAOYSA-N B(C1=C(C=C(C=C1)OC(C)CC)C=O)(O)O Chemical compound B(C1=C(C=C(C=C1)OC(C)CC)C=O)(O)O MWVUQGFFVPEIDF-UHFFFAOYSA-N 0.000 description 1
- AGTITJDHMFWLHR-UHFFFAOYSA-N B(C1=C(C=C(C=C1)OCC(C)C)C=O)(O)O Chemical compound B(C1=C(C=C(C=C1)OCC(C)C)C=O)(O)O AGTITJDHMFWLHR-UHFFFAOYSA-N 0.000 description 1
- CXIOQHFZHNDNQN-UHFFFAOYSA-N B(C1=C(C=C(C=C1)OCCC)C=O)(O)O Chemical compound B(C1=C(C=C(C=C1)OCCC)C=O)(O)O CXIOQHFZHNDNQN-UHFFFAOYSA-N 0.000 description 1
- MMRCAKVUKOXZJD-UHFFFAOYSA-N B(C1=C(C=CC(=C1)C(C)CC)C=O)(O)O Chemical compound B(C1=C(C=CC(=C1)C(C)CC)C=O)(O)O MMRCAKVUKOXZJD-UHFFFAOYSA-N 0.000 description 1
- GFBGUHSEDQVNKD-UHFFFAOYSA-N B(C1=C(C=CC(=C1)CC(C)C)C=O)(O)O Chemical compound B(C1=C(C=CC(=C1)CC(C)C)C=O)(O)O GFBGUHSEDQVNKD-UHFFFAOYSA-N 0.000 description 1
- VQCKJIFHBHQCAF-UHFFFAOYSA-N B(C1=C(C=CC(=C1)CC)C=O)(O)O Chemical compound B(C1=C(C=CC(=C1)CC)C=O)(O)O VQCKJIFHBHQCAF-UHFFFAOYSA-N 0.000 description 1
- GZPOKSSJQJESRY-UHFFFAOYSA-N B(C1=C(C=CC(=C1)CCC)C=O)(O)O Chemical compound B(C1=C(C=CC(=C1)CCC)C=O)(O)O GZPOKSSJQJESRY-UHFFFAOYSA-N 0.000 description 1
- YFYNEJZZROYERR-UHFFFAOYSA-N B(C1=C(C=CC(=C1)CCCC)C=O)(O)O Chemical compound B(C1=C(C=CC(=C1)CCCC)C=O)(O)O YFYNEJZZROYERR-UHFFFAOYSA-N 0.000 description 1
- BQHQBAVLNUZHPQ-UHFFFAOYSA-N B(C1=C(C=CC(=C1)OC(C)(C)C)C=O)(O)O Chemical compound B(C1=C(C=CC(=C1)OC(C)(C)C)C=O)(O)O BQHQBAVLNUZHPQ-UHFFFAOYSA-N 0.000 description 1
- QFEFITSGUBRKIF-UHFFFAOYSA-N B(C1=C(C=CC(=C1)OC(C)CC)C=O)(O)O Chemical compound B(C1=C(C=CC(=C1)OC(C)CC)C=O)(O)O QFEFITSGUBRKIF-UHFFFAOYSA-N 0.000 description 1
- ULXQHLFIGWJDMD-UHFFFAOYSA-N B(C1=C(C=CC(=C1)OCC(C)C)C=O)(O)O Chemical compound B(C1=C(C=CC(=C1)OCC(C)C)C=O)(O)O ULXQHLFIGWJDMD-UHFFFAOYSA-N 0.000 description 1
- RKTCZODDKWCNDT-UHFFFAOYSA-N B(C1=C(C=CC(=C1)OCCC)C=O)(O)O Chemical compound B(C1=C(C=CC(=C1)OCCC)C=O)(O)O RKTCZODDKWCNDT-UHFFFAOYSA-N 0.000 description 1
- ALMXMFXNKSLJJL-UHFFFAOYSA-N B(C1=C(C=CC(=C1)OCCCC)C=O)(O)O Chemical compound B(C1=C(C=CC(=C1)OCCCC)C=O)(O)O ALMXMFXNKSLJJL-UHFFFAOYSA-N 0.000 description 1
- UUVIDWYURRCUQZ-UHFFFAOYSA-N B(C1=CC(=C(C=C1)C(C)(C)C)C=O)(O)O Chemical compound B(C1=CC(=C(C=C1)C(C)(C)C)C=O)(O)O UUVIDWYURRCUQZ-UHFFFAOYSA-N 0.000 description 1
- HABHNEXDWAMJSB-UHFFFAOYSA-N B(C1=CC(=C(C=C1)C(C)CC)C=O)(O)O Chemical compound B(C1=CC(=C(C=C1)C(C)CC)C=O)(O)O HABHNEXDWAMJSB-UHFFFAOYSA-N 0.000 description 1
- DRELYKWODKFZOM-UHFFFAOYSA-N B(C1=CC(=C(C=C1)CC(C)C)C=O)(O)O Chemical compound B(C1=CC(=C(C=C1)CC(C)C)C=O)(O)O DRELYKWODKFZOM-UHFFFAOYSA-N 0.000 description 1
- BPPSMVZXNUAMKW-UHFFFAOYSA-N B(C1=CC(=C(C=C1)CC)C=O)(O)O Chemical compound B(C1=CC(=C(C=C1)CC)C=O)(O)O BPPSMVZXNUAMKW-UHFFFAOYSA-N 0.000 description 1
- SDYMTGZUJMFMFE-UHFFFAOYSA-N B(C1=CC(=C(C=C1)CCC)C=O)(O)O Chemical compound B(C1=CC(=C(C=C1)CCC)C=O)(O)O SDYMTGZUJMFMFE-UHFFFAOYSA-N 0.000 description 1
- ASFSXYDVIHAJIE-UHFFFAOYSA-N B(C1=CC(=C(C=C1)CCCC)C=O)(O)O Chemical compound B(C1=CC(=C(C=C1)CCCC)C=O)(O)O ASFSXYDVIHAJIE-UHFFFAOYSA-N 0.000 description 1
- IBXLLDOHEPVEKU-UHFFFAOYSA-N B(C1=CC(=C(C=C1)OC(C)(C)C)C=O)(O)O Chemical compound B(C1=CC(=C(C=C1)OC(C)(C)C)C=O)(O)O IBXLLDOHEPVEKU-UHFFFAOYSA-N 0.000 description 1
- UDVIATAESRFREH-UHFFFAOYSA-N B(C1=CC(=C(C=C1)OC(C)CC)C=O)(O)O Chemical compound B(C1=CC(=C(C=C1)OC(C)CC)C=O)(O)O UDVIATAESRFREH-UHFFFAOYSA-N 0.000 description 1
- RVRXCRIJYPEUBT-UHFFFAOYSA-N B(C1=CC(=C(C=C1)OCC(C)C)C=O)(O)O Chemical compound B(C1=CC(=C(C=C1)OCC(C)C)C=O)(O)O RVRXCRIJYPEUBT-UHFFFAOYSA-N 0.000 description 1
- WNGNIFFIEGWNLQ-UHFFFAOYSA-N B(C1=CC(=CC(=C1)C(C)(C)C)C=O)(O)O Chemical compound B(C1=CC(=CC(=C1)C(C)(C)C)C=O)(O)O WNGNIFFIEGWNLQ-UHFFFAOYSA-N 0.000 description 1
- QKPHKMZPDWLAIG-UHFFFAOYSA-N B(C1=CC(=CC(=C1)C(C)CC)C=O)(O)O Chemical compound B(C1=CC(=CC(=C1)C(C)CC)C=O)(O)O QKPHKMZPDWLAIG-UHFFFAOYSA-N 0.000 description 1
- NPCRQZQSMFUTJZ-UHFFFAOYSA-N B(C1=CC(=CC(=C1)C=O)CC(C)C)(O)O Chemical compound B(C1=CC(=CC(=C1)C=O)CC(C)C)(O)O NPCRQZQSMFUTJZ-UHFFFAOYSA-N 0.000 description 1
- RCXMEWSOKPSIKL-UHFFFAOYSA-N B(C1=CC(=CC(=C1)C=O)CC)(O)O Chemical compound B(C1=CC(=CC(=C1)C=O)CC)(O)O RCXMEWSOKPSIKL-UHFFFAOYSA-N 0.000 description 1
- LBGKYENLBUGNSZ-UHFFFAOYSA-N B(C1=CC(=CC(=C1)C=O)CCC)(O)O Chemical compound B(C1=CC(=CC(=C1)C=O)CCC)(O)O LBGKYENLBUGNSZ-UHFFFAOYSA-N 0.000 description 1
- YBWROZOUYXSLND-UHFFFAOYSA-N B(C1=CC(=CC(=C1)C=O)CCCC)(O)O Chemical compound B(C1=CC(=CC(=C1)C=O)CCCC)(O)O YBWROZOUYXSLND-UHFFFAOYSA-N 0.000 description 1
- UYWACUPOKNBYOE-UHFFFAOYSA-N B(C1=CC(=CC(=C1)OC(C)(C)C)C=O)(O)O Chemical compound B(C1=CC(=CC(=C1)OC(C)(C)C)C=O)(O)O UYWACUPOKNBYOE-UHFFFAOYSA-N 0.000 description 1
- ZVLSYYSYTDKLJO-UHFFFAOYSA-N B(C1=CC(=CC(=C1)OC(C)CC)C=O)(O)O Chemical compound B(C1=CC(=CC(=C1)OC(C)CC)C=O)(O)O ZVLSYYSYTDKLJO-UHFFFAOYSA-N 0.000 description 1
- AVYYCCHZRQOFDZ-UHFFFAOYSA-N B(C1=CC(=CC(=C1)OCC(C)C)C=O)(O)O Chemical compound B(C1=CC(=CC(=C1)OCC(C)C)C=O)(O)O AVYYCCHZRQOFDZ-UHFFFAOYSA-N 0.000 description 1
- UXCUMPFVDLLFOK-UHFFFAOYSA-N B(C1=CC(=CC=C1)C(=O)OC(C)CC)(O)O Chemical compound B(C1=CC(=CC=C1)C(=O)OC(C)CC)(O)O UXCUMPFVDLLFOK-UHFFFAOYSA-N 0.000 description 1
- GRORYWAZWBZMGM-UHFFFAOYSA-N B(C1=CC(=CC=C1)[Si](C(C)(C)C)(C(C)(C)C)C(C)(C)C)(O)O Chemical compound B(C1=CC(=CC=C1)[Si](C(C)(C)C)(C(C)(C)C)C(C)(C)C)(O)O GRORYWAZWBZMGM-UHFFFAOYSA-N 0.000 description 1
- UTTNOFUSSLVCKL-UHFFFAOYSA-N B(C1=CC(=CC=C1)[Si](C(C)C)(C(C)C)C(C)C)(O)O Chemical compound B(C1=CC(=CC=C1)[Si](C(C)C)(C(C)C)C(C)C)(O)O UTTNOFUSSLVCKL-UHFFFAOYSA-N 0.000 description 1
- PVJSSFKDVRDWEH-UHFFFAOYSA-N B(C1=CC(=CC=C1)[Si](CCC)(CCC)CCC)(O)O Chemical compound B(C1=CC(=CC=C1)[Si](CCC)(CCC)CCC)(O)O PVJSSFKDVRDWEH-UHFFFAOYSA-N 0.000 description 1
- GOMHXSWABYUJOX-UHFFFAOYSA-N B(C1=CC(=CC=C1)[Si](CCCC)(CCCC)CCCC)(O)O Chemical compound B(C1=CC(=CC=C1)[Si](CCCC)(CCCC)CCCC)(O)O GOMHXSWABYUJOX-UHFFFAOYSA-N 0.000 description 1
- MNEJPYRFUJGJJC-UHFFFAOYSA-N B(C1=CC=C(C=C1)[Si](C(C)(C)C)(C(C)(C)C)C(C)(C)C)(O)O Chemical compound B(C1=CC=C(C=C1)[Si](C(C)(C)C)(C(C)(C)C)C(C)(C)C)(O)O MNEJPYRFUJGJJC-UHFFFAOYSA-N 0.000 description 1
- POYSEZFZXXHQPI-UHFFFAOYSA-N B(C1=CC=C(C=C1)[Si](CCC)(CCC)CCC)(O)O Chemical compound B(C1=CC=C(C=C1)[Si](CCC)(CCC)CCC)(O)O POYSEZFZXXHQPI-UHFFFAOYSA-N 0.000 description 1
- VUVLBRVLIJEBMG-UHFFFAOYSA-N B(C1=CC=C(C=C1)[Si](CCCC)(CCCC)CCCC)(O)O Chemical compound B(C1=CC=C(C=C1)[Si](CCCC)(CCCC)CCCC)(O)O VUVLBRVLIJEBMG-UHFFFAOYSA-N 0.000 description 1
- BQBYBOUOVBCNHK-UHFFFAOYSA-N B(C1=CC=CC=C1C(=O)CCC)(O)O Chemical compound B(C1=CC=CC=C1C(=O)CCC)(O)O BQBYBOUOVBCNHK-UHFFFAOYSA-N 0.000 description 1
- UYEMBRSWAQCIMV-UHFFFAOYSA-N B(C1=CC=CC=C1C(=O)OCCC)(O)O Chemical compound B(C1=CC=CC=C1C(=O)OCCC)(O)O UYEMBRSWAQCIMV-UHFFFAOYSA-N 0.000 description 1
- RYQZQUGAUIOEKK-UHFFFAOYSA-N B(C1=CC=CC=C1NC(=O)CCC)(O)O Chemical compound B(C1=CC=CC=C1NC(=O)CCC)(O)O RYQZQUGAUIOEKK-UHFFFAOYSA-N 0.000 description 1
- VBMLDABROCNLIS-UHFFFAOYSA-N B(C1=CC=CC=C1[Si](C(C)CC)(C(C)CC)C(C)CC)(O)O Chemical compound B(C1=CC=CC=C1[Si](C(C)CC)(C(C)CC)C(C)CC)(O)O VBMLDABROCNLIS-UHFFFAOYSA-N 0.000 description 1
- QLASNHKSWARPKZ-UHFFFAOYSA-N B(C1=CC=CC=C1[Si](CCC)(CCC)CCC)(O)O Chemical compound B(C1=CC=CC=C1[Si](CCC)(CCC)CCC)(O)O QLASNHKSWARPKZ-UHFFFAOYSA-N 0.000 description 1
- FULZGMJVXIIADO-UHFFFAOYSA-N C(=CC)C1=C(C=CC=C1)B(O)O Chemical compound C(=CC)C1=C(C=CC=C1)B(O)O FULZGMJVXIIADO-UHFFFAOYSA-N 0.000 description 1
- UUONBHPWUGKXJD-UHFFFAOYSA-N C(=CC)C=1C=C(C=CC1)B(O)O Chemical compound C(=CC)C=1C=C(C=CC1)B(O)O UUONBHPWUGKXJD-UHFFFAOYSA-N 0.000 description 1
- PTNIKLQJMWLUBY-UHFFFAOYSA-N C(=CCC)C1=C(C=CC=C1)B(O)O Chemical compound C(=CCC)C1=C(C=CC=C1)B(O)O PTNIKLQJMWLUBY-UHFFFAOYSA-N 0.000 description 1
- JILWOIXKXYISBH-UHFFFAOYSA-N C(=CCC)C1=CC=C(C=C1)B(O)O Chemical compound C(=CCC)C1=CC=C(C=C1)B(O)O JILWOIXKXYISBH-UHFFFAOYSA-N 0.000 description 1
- YSBOXZOOVYLIEE-UHFFFAOYSA-N C(C)(=O)NC1=CC=C(C=C1)C(=C(F)F)F Chemical compound C(C)(=O)NC1=CC=C(C=C1)C(=C(F)F)F YSBOXZOOVYLIEE-UHFFFAOYSA-N 0.000 description 1
- QQGYMFUWNSTHAO-UHFFFAOYSA-N C(C)(C)[Si](C1=CC=C(C=C1)B(O)O)(C(C)C)C(C)C Chemical compound C(C)(C)[Si](C1=CC=C(C=C1)B(O)O)(C(C)C)C(C)C QQGYMFUWNSTHAO-UHFFFAOYSA-N 0.000 description 1
- NEPULMUUMKQSNX-UHFFFAOYSA-N C(C)C1=C(C=O)C=CC(=C1)C(=C(F)F)F Chemical compound C(C)C1=C(C=O)C=CC(=C1)C(=C(F)F)F NEPULMUUMKQSNX-UHFFFAOYSA-N 0.000 description 1
- DOGIKTAXIVPAGY-UHFFFAOYSA-N C(C=CC)C1=C(C=CC=C1)B(O)O Chemical compound C(C=CC)C1=C(C=CC=C1)B(O)O DOGIKTAXIVPAGY-UHFFFAOYSA-N 0.000 description 1
- VYSWQIWKCZASJW-UHFFFAOYSA-N C(C=CC)C=1C=C(C=CC1)B(O)O Chemical compound C(C=CC)C=1C=C(C=CC1)B(O)O VYSWQIWKCZASJW-UHFFFAOYSA-N 0.000 description 1
- ASEQINSSHIASPN-UHFFFAOYSA-N C(CC(C)C)(=O)C1=C(C=CC=C1)B(O)O Chemical compound C(CC(C)C)(=O)C1=C(C=CC=C1)B(O)O ASEQINSSHIASPN-UHFFFAOYSA-N 0.000 description 1
- LELUQDVTPZAQND-UHFFFAOYSA-N C(CC(C)C)(=O)NC1=C(C=CC=C1)B(O)O Chemical compound C(CC(C)C)(=O)NC1=C(C=CC=C1)B(O)O LELUQDVTPZAQND-UHFFFAOYSA-N 0.000 description 1
- JDHGGRBSEYQRPW-UHFFFAOYSA-N C(CCCC)(=O)C1=C(C=CC=C1)B(O)O Chemical compound C(CCCC)(=O)C1=C(C=CC=C1)B(O)O JDHGGRBSEYQRPW-UHFFFAOYSA-N 0.000 description 1
- PGIALYIRFMVPMF-UHFFFAOYSA-N C(CCCC)(=O)NC1=C(C=CC=C1)B(O)O Chemical compound C(CCCC)(=O)NC1=C(C=CC=C1)B(O)O PGIALYIRFMVPMF-UHFFFAOYSA-N 0.000 description 1
- LPKODNINELGCIA-UHFFFAOYSA-N CC(C)C(=O)NC1=CC=CC=C1B(O)O Chemical compound CC(C)C(=O)NC1=CC=CC=C1B(O)O LPKODNINELGCIA-UHFFFAOYSA-N 0.000 description 1
- BTMWGAUQQTZKHN-UHFFFAOYSA-N CCC(C)OC(=O)C1=CC=C(C=C1)B(O)O Chemical compound CCC(C)OC(=O)C1=CC=C(C=C1)B(O)O BTMWGAUQQTZKHN-UHFFFAOYSA-N 0.000 description 1
- BGMYWBBURKZZRX-UHFFFAOYSA-N COC1=C(C=O)C=C(C=C1)C(=C(F)F)F Chemical compound COC1=C(C=O)C=C(C=C1)C(=C(F)F)F BGMYWBBURKZZRX-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- LRULVYSBRWUVGR-FCHUYYIVSA-N GSK2879552 Chemical compound C1=CC(C(=O)O)=CC=C1CN1CCC(CN[C@H]2[C@@H](C2)C=2C=CC=CC=2)CC1 LRULVYSBRWUVGR-FCHUYYIVSA-N 0.000 description 1
- VKXZJMSMWLJLLW-UHFFFAOYSA-N NC(c1ccccc1)=C(N)N Chemical compound NC(c1ccccc1)=C(N)N VKXZJMSMWLJLLW-UHFFFAOYSA-N 0.000 description 1
- BLJTTZQBZGMVDA-UHFFFAOYSA-N NC1=C(C=CC(=C1)C)[B] Chemical compound NC1=C(C=CC(=C1)C)[B] BLJTTZQBZGMVDA-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- UQONAEXHTGDOIH-AWEZNQCLSA-N O=C(N1CC[C@@H](C1)N1CCCC1=O)C1=CC2=C(NC3(CC3)CCO2)N=C1 Chemical compound O=C(N1CC[C@@H](C1)N1CCCC1=O)C1=CC2=C(NC3(CC3)CCO2)N=C1 UQONAEXHTGDOIH-AWEZNQCLSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 238000006161 Suzuki-Miyaura coupling reaction Methods 0.000 description 1
- MCRWZBYTLVCCJJ-DKALBXGISA-N [(1s,3r)-3-[[(3s,4s)-3-methoxyoxan-4-yl]amino]-1-propan-2-ylcyclopentyl]-[(1s,4s)-5-[6-(trifluoromethyl)pyrimidin-4-yl]-2,5-diazabicyclo[2.2.1]heptan-2-yl]methanone Chemical compound C([C@]1(N(C[C@]2([H])C1)C(=O)[C@@]1(C[C@@H](CC1)N[C@@H]1[C@@H](COCC1)OC)C(C)C)[H])N2C1=CC(C(F)(F)F)=NC=N1 MCRWZBYTLVCCJJ-DKALBXGISA-N 0.000 description 1
- VZVDPGLLBNZTSL-UHFFFAOYSA-N [2-(2,2-dimethylpropanoyl)phenyl]boronic acid Chemical compound CC(C)(C)C(=O)C1=CC=CC=C1B(O)O VZVDPGLLBNZTSL-UHFFFAOYSA-N 0.000 description 1
- MXRAJVMTCAUABO-UHFFFAOYSA-N [2-(2,2-dimethylpropanoylamino)phenyl]boronic acid Chemical compound CC(C)(C)C(=O)NC1=CC=CC=C1B(O)O MXRAJVMTCAUABO-UHFFFAOYSA-N 0.000 description 1
- GJIQSSSNYDILOS-UHFFFAOYSA-N [2-(2-methylpropanoyl)phenyl]boronic acid Chemical compound CC(C)C(=O)C1=CC=CC=C1B(O)O GJIQSSSNYDILOS-UHFFFAOYSA-N 0.000 description 1
- ODUIXUGXPFKQLG-QWRGUYRKSA-N [2-(4-chloro-2-fluoroanilino)-5-methyl-1,3-thiazol-4-yl]-[(2s,3s)-2,3-dimethylpiperidin-1-yl]methanone Chemical compound C[C@H]1[C@@H](C)CCCN1C(=O)C1=C(C)SC(NC=2C(=CC(Cl)=CC=2)F)=N1 ODUIXUGXPFKQLG-QWRGUYRKSA-N 0.000 description 1
- YJOCMAAPKZMJBR-UHFFFAOYSA-N [2-(propanoylamino)phenyl]boronic acid Chemical compound CCC(=O)NC1=CC=CC=C1B(O)O YJOCMAAPKZMJBR-UHFFFAOYSA-N 0.000 description 1
- STNQVBCAMCAFKC-UHFFFAOYSA-N [2-[(2-methylpropan-2-yl)oxy]phenyl]boronic acid Chemical compound CC(C)(C)OC1=CC=CC=C1B(O)O STNQVBCAMCAFKC-UHFFFAOYSA-N 0.000 description 1
- NGCHASOIZPPFBK-UHFFFAOYSA-N [2-[(2-methylpropan-2-yl)oxycarbonyl]phenyl]boronic acid Chemical compound CC(C)(C)OC(=O)C1=CC=CC=C1B(O)O NGCHASOIZPPFBK-UHFFFAOYSA-N 0.000 description 1
- LXGQHDUCNDGTDB-PAMNCVQHSA-N [2-[(8s,9r,10s,13s,14s,16s,17r)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate;[2-[(8s,9r,10s,13s,14s,16s,17r)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11, Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)COC(C)=O)(O)[C@@]1(C)CC2O.C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)COP(O)(O)=O)(O)[C@@]1(C)CC2O LXGQHDUCNDGTDB-PAMNCVQHSA-N 0.000 description 1
- LKLYKTFDBGKKSS-UHFFFAOYSA-N [3-(2,2-dimethylpropanoyl)phenyl]boronic acid Chemical compound CC(C)(C)C(=O)C1=CC=CC(B(O)O)=C1 LKLYKTFDBGKKSS-UHFFFAOYSA-N 0.000 description 1
- FCFJZCTYFIECHV-UHFFFAOYSA-N [3-(2-methylpropanoyl)phenyl]boronic acid Chemical compound CC(C)C(=O)C1=CC=CC(B(O)O)=C1 FCFJZCTYFIECHV-UHFFFAOYSA-N 0.000 description 1
- HXBVOKMSEWLCKA-UHFFFAOYSA-N [3-(2-methylpropanoylamino)phenyl]boronic acid Chemical compound CC(C)C(=O)NC1=CC=CC(B(O)O)=C1 HXBVOKMSEWLCKA-UHFFFAOYSA-N 0.000 description 1
- LRVNWWSPVGZJSF-UHFFFAOYSA-N [3-(3-methylbutanoyl)phenyl]boronic acid Chemical compound CC(C)CC(=O)C1=CC=CC(B(O)O)=C1 LRVNWWSPVGZJSF-UHFFFAOYSA-N 0.000 description 1
- YSTOTUBRPRPJHA-UHFFFAOYSA-N [3-(3-methylbutanoylamino)phenyl]boronic acid Chemical compound CC(C)CC(=O)NC1=CC=CC(B(O)O)=C1 YSTOTUBRPRPJHA-UHFFFAOYSA-N 0.000 description 1
- WKBFEWURUDLFFY-UHFFFAOYSA-N [3-(butanoylamino)phenyl]boronic acid Chemical compound CCCC(=O)NC1=CC=CC(B(O)O)=C1 WKBFEWURUDLFFY-UHFFFAOYSA-N 0.000 description 1
- OWHHCOKJBCMMOX-UHFFFAOYSA-N [3-(propanoylamino)phenyl]boronic acid Chemical compound CCC(=O)NC1=CC=CC(B(O)O)=C1 OWHHCOKJBCMMOX-UHFFFAOYSA-N 0.000 description 1
- NHNUYDRSOHYBSP-UHFFFAOYSA-N [3-[(2-methylpropan-2-yl)oxy]phenyl]boronic acid Chemical compound CC(C)(C)OC1=CC=CC(B(O)O)=C1 NHNUYDRSOHYBSP-UHFFFAOYSA-N 0.000 description 1
- HVJDVHCPCSZDSR-UHFFFAOYSA-N [3-[(2-methylpropan-2-yl)oxycarbonyl]phenyl]boronic acid Chemical compound CC(C)(C)OC(=O)C1=CC=CC(B(O)O)=C1 HVJDVHCPCSZDSR-UHFFFAOYSA-N 0.000 description 1
- ABJLQQGXHGSDGJ-UHFFFAOYSA-N [4-(2,2-dimethylpropanoyl)phenyl]boronic acid Chemical compound CC(C)(C)C(=O)C1=CC=C(B(O)O)C=C1 ABJLQQGXHGSDGJ-UHFFFAOYSA-N 0.000 description 1
- CFUNNCDOCRSHJT-UHFFFAOYSA-N [4-(2-methylpropanoyl)phenyl]boronic acid Chemical compound CC(C)C(=O)C1=CC=C(B(O)O)C=C1 CFUNNCDOCRSHJT-UHFFFAOYSA-N 0.000 description 1
- DBWRRIVRDITVFV-UHFFFAOYSA-N [4-(2-methylpropanoylamino)phenyl]boronic acid Chemical compound CC(C)C(=O)NC1=CC=C(B(O)O)C=C1 DBWRRIVRDITVFV-UHFFFAOYSA-N 0.000 description 1
- HFIQYDWQIGRTGC-UHFFFAOYSA-N [4-(3-methylbutanoyl)phenyl]boronic acid Chemical compound CC(C)CC(=O)C1=CC=C(B(O)O)C=C1 HFIQYDWQIGRTGC-UHFFFAOYSA-N 0.000 description 1
- IYIJQCANLYFTLT-UHFFFAOYSA-N [4-(3-methylbutanoylamino)phenyl]boronic acid Chemical compound CC(C)CC(=O)NC1=CC=C(B(O)O)C=C1 IYIJQCANLYFTLT-UHFFFAOYSA-N 0.000 description 1
- RUUADMXVPYHFKN-UHFFFAOYSA-N [4-(butanoylamino)phenyl]boronic acid Chemical compound CCCC(=O)Nc1ccc(cc1)B(O)O RUUADMXVPYHFKN-UHFFFAOYSA-N 0.000 description 1
- MWMLMKYIVVQMHD-UHFFFAOYSA-N [4-(pentanoylamino)phenyl]boronic acid Chemical compound CCCCC(=O)NC1=CC=C(B(O)O)C=C1 MWMLMKYIVVQMHD-UHFFFAOYSA-N 0.000 description 1
- GFMJBBAAKDKKCC-UHFFFAOYSA-N [4-(propanoylamino)phenyl]boronic acid Chemical compound CCC(=O)NC1=CC=C(B(O)O)C=C1 GFMJBBAAKDKKCC-UHFFFAOYSA-N 0.000 description 1
- OKHCKPPOCZWHRN-UHFFFAOYSA-N [4-[(2-methylpropan-2-yl)oxy]phenyl]boronic acid Chemical compound CC(C)(C)OC1=CC=C(B(O)O)C=C1 OKHCKPPOCZWHRN-UHFFFAOYSA-N 0.000 description 1
- XXKVCXDNRANROA-UHFFFAOYSA-N [B]C1=CC(=CC=C1)NC(=O)CCCC Chemical compound [B]C1=CC(=CC=C1)NC(=O)CCCC XXKVCXDNRANROA-UHFFFAOYSA-N 0.000 description 1
- NDFWAUNAFRZGAZ-UHFFFAOYSA-N [dichloro(diphenylphosphanyl)methyl]-diphenylphosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C(Cl)(Cl)P(C=1C=CC=CC=1)C1=CC=CC=C1 NDFWAUNAFRZGAZ-UHFFFAOYSA-N 0.000 description 1
- RBYGDVHOECIAFC-UHFFFAOYSA-L acetonitrile;palladium(2+);dichloride Chemical compound [Cl-].[Cl-].[Pd+2].CC#N.CC#N RBYGDVHOECIAFC-UHFFFAOYSA-L 0.000 description 1
- WXNOJTUTEXAZLD-UHFFFAOYSA-L benzonitrile;dichloropalladium Chemical compound Cl[Pd]Cl.N#CC1=CC=CC=C1.N#CC1=CC=CC=C1 WXNOJTUTEXAZLD-UHFFFAOYSA-L 0.000 description 1
- WXMZPPIDLJRXNK-UHFFFAOYSA-N butyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(CCCC)C1=CC=CC=C1 WXMZPPIDLJRXNK-UHFFFAOYSA-N 0.000 description 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- WMKGGPCROCCUDY-PHEQNACWSA-N dibenzylideneacetone Chemical compound C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 WMKGGPCROCCUDY-PHEQNACWSA-N 0.000 description 1
- QDGONURINHVBEW-UHFFFAOYSA-N dichlorodifluoroethylene Chemical group FC(F)=C(Cl)Cl QDGONURINHVBEW-UHFFFAOYSA-N 0.000 description 1
- CCAFPWNGIUBUSD-UHFFFAOYSA-N diethyl sulfoxide Chemical compound CCS(=O)CC CCAFPWNGIUBUSD-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- JMZFEHDNIAQMNB-UHFFFAOYSA-N m-aminophenylboronic acid Chemical compound NC1=CC=CC(B(O)O)=C1 JMZFEHDNIAQMNB-UHFFFAOYSA-N 0.000 description 1
- SKTCDJAMAYNROS-UHFFFAOYSA-N methoxycyclopentane Chemical compound COC1CCCC1 SKTCDJAMAYNROS-UHFFFAOYSA-N 0.000 description 1
- VZUGBLTVBZJZOE-KRWDZBQOSA-N n-[3-[(4s)-2-amino-1,4-dimethyl-6-oxo-5h-pyrimidin-4-yl]phenyl]-5-chloropyrimidine-2-carboxamide Chemical compound N1=C(N)N(C)C(=O)C[C@@]1(C)C1=CC=CC(NC(=O)C=2N=CC(Cl)=CN=2)=C1 VZUGBLTVBZJZOE-KRWDZBQOSA-N 0.000 description 1
- VOVZXURTCKPRDQ-CQSZACIVSA-N n-[4-[chloro(difluoro)methoxy]phenyl]-6-[(3r)-3-hydroxypyrrolidin-1-yl]-5-(1h-pyrazol-5-yl)pyridine-3-carboxamide Chemical compound C1[C@H](O)CCN1C1=NC=C(C(=O)NC=2C=CC(OC(F)(F)Cl)=CC=2)C=C1C1=CC=NN1 VOVZXURTCKPRDQ-CQSZACIVSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- XULSCZPZVQIMFM-IPZQJPLYSA-N odevixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)N[C@@H](CC)C(O)=O)C=3C=CC(O)=CC=3)C=C2S(=O)(=O)NC(CCCC)(CCCC)CN1C1=CC=CC=C1 XULSCZPZVQIMFM-IPZQJPLYSA-N 0.000 description 1
- PENAXHPKEVTBLF-UHFFFAOYSA-L palladium(2+);prop-1-ene;dichloride Chemical class [Pd+]Cl.[Pd+]Cl.[CH2-]C=C.[CH2-]C=C PENAXHPKEVTBLF-UHFFFAOYSA-L 0.000 description 1
- JKDRQYIYVJVOPF-FDGPNNRMSA-L palladium(ii) acetylacetonate Chemical compound [Pd+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O JKDRQYIYVJVOPF-FDGPNNRMSA-L 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000004262 preparative liquid chromatography Methods 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005930 sec-butyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- NZMOFYDMGFQZLS-UHFFFAOYSA-N terazosin hydrochloride dihydrate Chemical compound [H+].O.O.[Cl-].N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1CCCO1 NZMOFYDMGFQZLS-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000002306 tributylsilyl group Chemical group C(CCC)[Si](CCCC)(CCCC)* 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
- TXABOOAVXFFJQL-UHFFFAOYSA-N trimethyl-[4-(1,2,2-trifluoroethenyl)phenyl]silane Chemical compound C[Si](C)(C)C1=CC=C(C(F)=C(F)F)C=C1 TXABOOAVXFFJQL-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- KMIOJWCYOHBUJS-HAKPAVFJSA-N vorolanib Chemical compound C1N(C(=O)N(C)C)CC[C@@H]1NC(=O)C1=C(C)NC(\C=C/2C3=CC(F)=CC=C3NC\2=O)=C1C KMIOJWCYOHBUJS-HAKPAVFJSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Description
Tetrahedron Letters,38巻,3844ページ,1997年 The Journal of Organic Chemistry,62巻,6459ページ,1997年 The Chemistry of Metal−Carbon Bond,Wiley社,1987年,第4巻,307−499ページ。 Pure and Applied Chemistry,78巻,1369ページ,2006年
2−フルオロ−4−ホルミルフェニルボロン酸、3−フルオロ−4−ホルミルフェニルボロン酸、5−フルオロ−3−ホルミルフェニルボロン酸、1−ナフチルボロン酸、2−ナフチルボロン酸等のボロン酸類を例示できる。
実施例−1
ム7.3mg(0.01mmol)、3−ニトロフェニルボロン酸167mg(1.0mmol)、及び炭酸ナトリウム212mg(2.0mmol)を加え、アルゴン置換した後、1,4−ジオキサン2mL、水0.3mL(16.7mmol)を加えた。この混合物を、−196℃に冷却しクロロトリフルオロエチレン466mg(4.0mmol)を加え、アルゴン気流下にて密閉し、100℃に加熱し2時間攪拌した。反応後、ガスクロマトグラフィーにより1−ニトロ−3−(トリフルオロビニル)ベンゼンの生成を確認した(GC収率84%)。混合物をろ過し、ろ液を濃縮して得られた残渣をシリカゲルカラムクロマトグラフィーにより精製し、1−ニトロ−3−(トリフルオロビニル)ベンゼン162mgを得た(収率77%)。
1H−NMR(CDCl3,400MHz)δ7.65(t,1H,J=8.1Hz),7.80(d,1H,J=8.1Hz),8.22(dd,1H,J=2.0Hz,J=8.1Hz),8.35(t,1H,J=2.0Hz).
19F−NMR(CDCl3,376MHz)δ−177.3(dd,J=34.0Hz,110.2Hz,1F),−111.0(dd,J=62.8Hz,110.2Hz,1F),−95.7(dd,J=34.0Hz,62.8Hz,1F).
比較例−1
比較例−2
比較例−3
実施例−2
実施例−3
実施例−4
1H−NMR(CDCl3,400MHz)δ3.94(s,3H),7.54(d,J=8.4Hz,2H),8.09(d,J=8.4Hz,2H).
19F−NMR(CDCl3,376MHz)δ−177.5(dd,J=33.0Hz,108.6Hz,1F),−111.3(dd,J=63.0Hz,108.6Hz,1F),−96.7(dd,J=33.0Hz,63.0Hz,1F).
実施例−5
1H−NMR(CDCl3,400MHz)δ2.62(s,3H),7.57(d,J=8.4Hz,2H),8.01(d,J=8.4Hz,2H).
19F−NMR(CDCl3,376MHz)δ−177.5(dd,J=33.3Hz,108.2Hz,1F),−111.1(dd,J=62.0Hz,108.2Hz,1F),−96.3(dd,J=33.3Hz,62.0Hz,1F).
実施例−6
1H−NMR(CDCl3,400MHz)δ7.59(d,J=8.5Hz,2H),7.72(d,J=8.5Hz,2H).
19F−NMR(CDCl3,376MHz)δ−178.0(dd,J=34.0Hz,108.8Hz,1F),−109.7(dd,J=59.7Hz,108.8Hz,1F),−96.3(dd,J=34.0Hz,59.7Hz,1F).
実施例−7
実施例−8
1H−NMR(CDCl3,400MHz)δ7.35(t,J=7.3Hz,1H),7.43(t,J=7.3Hz,2H),7.51(d,J=8.3Hz,2H),7.57(d,J=8.3Hz,2H),7.62(d,J=8.3Hz,2H).
19F−NMR(CDCl3,376MHz)δ−176.8(dd,J=32.3Hz,108.9Hz,1F),−114.4(dd,J=70.7Hz,108.9Hz,1F),−99.5(dd,J=32.3Hz,70.7Hz,1F).
実施例−9
実施例−10
実施例−11
1H−NMR(CDCl3,400MHz)δ1.33(s,9H),7.40(d,J=8.7Hz,2H),7.45(d,J=8.7Hz,2H).
19F−NMR(CDCl3,376MHz)δ−176.7(dd,J=32.3Hz,109.7Hz,1F),−115.8(dd,J=73.5Hz,109.7Hz,1F),−100.8(dd,J=32.3Hz,73.5Hz,1F).
実施例−12
1H−NMR(CDCl3,400MHz)δ1.38(d,J=6.0Hz,6H),4.66(sept,J=6.0Hz,1H),7.22(s,1H),7.36(s,1H),7.50(s,1H),9.96(s,1H).
19F−NMR(CDCl3,376MHz)δ−176.8(dd,J=33.0Hz,109.6Hz,1F),−112.2(dd,J=66.4Hz,109.6Hz,1F),−97.5(dd,J=33.0Hz,66.4Hz,1F).
実施例−13
実施例−14
1H−NMR(CDCl3,400MHz)δ7.40(s,4H).
19F−NMR(CDCl3,376MHz)δ−176.9(dd,J=32.7Hz,109.8Hz,1F),−113.7(dd,J=69.4Hz,109.8Hz,1F),−98.9(dd,J=32.7Hz,69.4Hz,1F).
実施例−15
1H−NMR(CDCl3,400MHz)δ1.25(t,J=7.6Hz,3H),2.67(q,J=7.6Hz,2H),7.25(d,J=8.2Hz,2H),7.38(d,J=8.2Hz,2H).
19F−NMR(CDCl3,376MHz)δ−176.4(dd,J=32.5Hz,109.1Hz,1F),−115.8(dd,J=73.8Hz,109.1Hz,1F),−100.9(dd,J=32.5Hz,73.8Hz,1F).
実施例−16
1H−NMR(CDCl3,400MHz)δ5.31(d,J=10.9Hz,1H),5.80(d,J=17.6Hz,1H),6.71(dd,J=10.9Hz,17.6Hz,1H),7.42(d,J=8.6Hz,2H),7.45(d,J=8.6Hz,2H).
19F−NMR(CDCl3,376MHz)δ−177.0(dd,J=32.5Hz,108.8Hz,1F),−114.3(dd,J=70.4Hz,108.8Hz,1F),−99.6(dd,J=32.5Hz,70.4Hz,1F).
実施例−17
1H−NMR(CDCl3,400MHz)δ3.81(s,3H),6.89(dd,J=2.5Hz,8.3Hz,1H),7.00(t,J=2.1Hz,1H),7.05(dd,J=0.7Hz,7.8Hz,1H),7.32(t,J=8.0Hz,1H).
19F−NMR(CDCl3,376MHz)δ−176.3(dd,J=32.6Hz,108.9Hz,1F),−113.9(dd,J=69.8Hz,108.9Hz,1F),−99.5(dd,J=32.6Hz,69.8Hz,1F).
実施例−18
1H−NMR(CDCl3,400MHz)δ2.20(s,3H),7.19(s,1H),7.43(d,J=8.6Hz,2H),7.58(d,J=8.6Hz,2H),19F−NMR(CDCl3,376MHz)δ−176.6(dd,J=32.3Hz,109.3Hz,1F),−115.5(dd,J=73.1Hz,109.3Hz,1F),−100.5(dd,J=32.3Hz,73.1Hz,1F).
実施例−19
1H−NMR(CDCl3,400MHz)δ3.86(s,3H),6.94−7.01(m,2H),7.32(d,J=7.6Hz,1H),7.41(ddt,J=1.4Hz,J=1.4Hz,J=7.9Hz,1H).
19F−NMR(CDCl3,376MHz)δ−164.9(dd,J=29.6Hz,114.9Hz,1F),−116.4(dd,J=73.2Hz,114.9Hz,1F),−102.3(dd,J=29.6Hz,73.2Hz,1F).
実施例−20
1H−NMR(CDCl3,400MHz)δ0.28(s,9H),7.44(d,J=8.0Hz,2H),7.57(d,J=8.0Hz,2H).
19F−NMR(CDCl3,376MHz)δ−177.3(dd,J=32.3Hz,109.1Hz,1F),−114.3(dd,J=69.9Hz,109.1Hz,1F),−100.8(dd,J=32.3Hz,69.9Hz,1F).
実施例−21
1H−NMR(CDCl3,400MHz)δ7.94(d,J=2.4Hz,1H),7.65(dd,J=2.4Hz,8.8Hz,1H),7.07(d,J=8.8Hz,1H).
19F−NMR(CDCl3,376MHz)δ−176.2(dd,J=32.6Hz,110.3Hz,1F),−115.5(dd,J=73.5Hz,110.3Hz,1F),−100.2(dd,J=32.6Hz,73.5Hz,1F).
実施例−22
1H−NMR(CDCl3,400MHz)δ10.36(s,1H),7.94(dd,J=8.0Hz,1H),7.31(dd,J=1.5Hz,11.4Hz,1H),7.39(d,J=8.0Hz,1H).
19F−NMR(CDCl3,376MHz)δ−177.2(ddd,J=3.8Hz,33.5Hz,108.4Hz,1F),−120.6(d,J=3.8Hz,1F),−108.1(dd,J=55.3Hz,108.4Hz,1F),−93.5(dd,J=33.5Hz,55.3Hz,1F).
実施例−23
1H−NMR(CDCl3,400MHz)δ10.29(s,1H),7.88(d,J=8.2Hz,1H),7.47(d,J=8.2Hz,1H),7.41(s,1H),3.10(q,J=7.6Hz,2H),1.29(t,J=7.6Hz,3H).
19F−NMR(CDCl3,376MHz)δ−177.5(dd,J=33.2Hz,108.2Hz,1F),−110.3(dd,J=60.6Hz,108.2Hz,1F),−95.7(dd,J=33.2Hz,60.6Hz,1F).
実施例−24
1H−NMR(CDCl3,400MHz)δ7.50−7.57(m,3H),7.81−7.88(m,3H),7.95(d,J=1.2Hz,1H),19F−NMR(CDCl3,376MHz)δ−176.2(dd,J=32.0Hz,108.5Hz,1F),−114.3(dd,J=70.5Hz,108.5Hz,1F),−99.1(dd,J=32.0Hz,70.5Hz,1F).
実施例−25
1H−NMR(CDCl3,400MHz)δ7.47−7.60(m,4H),7.88−8.02(m,4H),19F−NMR(CDCl3,376MHz)δ−159.9(dd,J=29.2Hz,117.5Hz,1F),−117.1(dd,J=73.9Hz,117.5Hz,1F),−101.5(dd,J=29.2Hz,73.9Hz,1F).
実施例−26
実施例−27
Claims (7)
- 一般式(1)
- Xが、塩素原子である請求項1に記載の製造方法。
- 二座ホスフィン配位子が、1,4−ビス(ジフェニルホスフィノ)ブタンまたは1,1’−ビス(ジフェニルホスフィノ)フェロセンである請求項1または2に記載の製造方法。
- 二座ホスフィン配位子が配位したパラジウム錯体が、ジクロロ[1,1’−ビス(ジフェニルホスフィノ)フェロセン]パラジウム又はジクロロ[1,4−ビス(ジフェニルホスフィノ)ブタン]パラジウムである請求項1または2に記載の製造方法。
- 二座ホスフィン配位子が配位したパラジウム錯体が、1,4−ビス(ジフェニルホスフィノ)ブタン又は1,1’−ビス(ジフェニルホスフィノ)フェロセンと、ビス(ジベンジリデンアセトン)パラジウムとから合成したパラジウム錯体である請求項1または2に記載の製造方法。
- アルカリ金属塩が、炭酸カリウム、炭酸ナトリウム、フッ化カリウムまたはフッ化セシウムである請求項1から5のいずれかに記載の製造方法。
- フェニルホウ素化合物(1)に対して2〜50当量の水の共存下で反応を実施する請求項1から6のいずれかに記載の製造方法。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2011202530A JP5833392B2 (ja) | 2010-09-17 | 2011-09-16 | (トリフルオロビニル)ベンゼン類およびその製造方法 |
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2010208769 | 2010-09-17 | ||
JP2010208769 | 2010-09-17 | ||
JP2010232100 | 2010-10-15 | ||
JP2010232100 | 2010-10-15 | ||
JP2011202530A JP5833392B2 (ja) | 2010-09-17 | 2011-09-16 | (トリフルオロビニル)ベンゼン類およびその製造方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2012102073A JP2012102073A (ja) | 2012-05-31 |
JP5833392B2 true JP5833392B2 (ja) | 2015-12-16 |
Family
ID=46392924
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2011202530A Active JP5833392B2 (ja) | 2010-09-17 | 2011-09-16 | (トリフルオロビニル)ベンゼン類およびその製造方法 |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP5833392B2 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9615155B2 (en) | 2012-06-07 | 2017-04-04 | Yamaha Corporation | Speaker apparatus and speaker box |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP6410072B2 (ja) * | 2013-02-18 | 2018-10-24 | ダイキン工業株式会社 | 有機基で置換された含フッ素オレフィンの製造方法 |
EA030705B1 (ru) * | 2013-03-06 | 2018-09-28 | Инсайт Холдингс Корпорейшн | Способы и промежуточные соединения при получении ингибитора jak |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4721791A (en) * | 1984-02-02 | 1988-01-26 | Merck & Co., Inc. | 5-amino or substituted amino 1,2,3-triazoles |
EP2684859B1 (en) * | 2011-03-10 | 2023-06-14 | Osaka University | Preparation method for fluorine-containing olefins having organic-group substituents |
-
2011
- 2011-09-16 JP JP2011202530A patent/JP5833392B2/ja active Active
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9615155B2 (en) | 2012-06-07 | 2017-04-04 | Yamaha Corporation | Speaker apparatus and speaker box |
Also Published As
Publication number | Publication date |
---|---|
JP2012102073A (ja) | 2012-05-31 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
Semba et al. | Copper-catalyzed borylative transformations of non-polar carbon–carbon unsaturated compounds employing borylcopper as an active catalyst species | |
Kambe et al. | Pd-catalyzed cross-coupling reactions of alkyl halides | |
Suginome et al. | Regio-and stereoselective synthesis of (Z)-β-silylalkenylboranes by silaboration of alkynes catalyzed by palladium and platinum complexes | |
JP4188318B2 (ja) | 非環状オレフィンのテロメリゼーションのための方法 | |
Wang et al. | Easy access to enamides: a mild nickel-catalysed alkene isomerization of allylamides | |
US9598335B2 (en) | Method for producing fluorine-containing olefin | |
KR101915491B1 (ko) | 비아릴 제조방법 | |
Özdemir et al. | Use of tetrahydropyrimidinium salts for highly efficient palladium-catalyzed cross-coupling reactions of aryl bromides and chlorides | |
JPWO2013099819A1 (ja) | バナジウム錯体を用いたファルネサールの製造方法 | |
JP5833392B2 (ja) | (トリフルオロビニル)ベンゼン類およびその製造方法 | |
CN111420709A (zh) | 氮杂环卡宾基混配型镍(ii)配合物在合成2-直链烷基苯并噻唑类化合物反应中的应用 | |
US20060122398A1 (en) | Novel nickel-carbene, palladium-carbene and platinum-carbene complexes, their produciton and use in catalytic reactions | |
US6642401B2 (en) | β-diketonatocopper(I) complex containing allene compounds as ligand and process for producing the same | |
Hyuga et al. | (E)-(2-bromoethenyl) dibromoborane. A new precursor for (E)-1, 2-disubstituted ethenes | |
EP3337808A1 (en) | Method for coupling an aromatic or vinylic compound to a boron-containing compound | |
Hosoi et al. | Palladium-catalyzed cross-coupling reaction using alkenyldimethyl (2-thienyl) silanes | |
Sato et al. | Formation of quaternary carbon center with a trifluoromethyl group using a Pd-catalyzed allylation reaction | |
JP5261140B2 (ja) | ビニル芳香族化合物の製造方法 | |
Karuo et al. | Synthesis of aryl 2-bromo-2-chloro-1, 1-difluoroethyl ethers through the base-mediated reaction between phenols and halothane | |
Ansorge et al. | Synthesis and structure of the chromiumcarbonyl complexed phenyl allene | |
JP4635251B2 (ja) | 有機ビスマス化合物およびその製法 | |
KR20220143880A (ko) | 알킬 2-벤조일벤조에이트의 효율적이고 선택적인 합성 경로 | |
JP4552405B2 (ja) | ビアリール化合物類の製造方法 | |
JP3443908B2 (ja) | アリルアルコール類の製造方法 | |
JP5869957B2 (ja) | 1,2−ビス(ビス(多置換フェニル)ホスフィノ)ベンゼン配位ニッケル(ii)錯体およびその製造方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20140714 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20150219 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20150324 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20150515 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20151027 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20151029 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5833392 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
S111 | Request for change of ownership or part of ownership |
Free format text: JAPANESE INTERMEDIATE CODE: R313115 |
|
R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
S531 | Written request for registration of change of domicile |
Free format text: JAPANESE INTERMEDIATE CODE: R313531 |
|
R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |