JP2018516843A - Ｓｕｚｕｋｉカップリング後のパラジウムの回収及び／または再利用 - Google Patents
Ｓｕｚｕｋｉカップリング後のパラジウムの回収及び／または再利用 Download PDFInfo
- Publication number
- JP2018516843A JP2018516843A JP2017547544A JP2017547544A JP2018516843A JP 2018516843 A JP2018516843 A JP 2018516843A JP 2017547544 A JP2017547544 A JP 2017547544A JP 2017547544 A JP2017547544 A JP 2017547544A JP 2018516843 A JP2018516843 A JP 2018516843A
- Authority
- JP
- Japan
- Prior art keywords
- suzuki coupling
- palladium
- palladium catalyst
- coupling reaction
- alkyl
- 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.)
- Withdrawn
Links
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 title claims abstract description 283
- 229910052763 palladium Inorganic materials 0.000 title claims abstract description 130
- 238000006069 Suzuki reaction reaction Methods 0.000 title claims abstract description 97
- 238000011084 recovery Methods 0.000 title claims description 26
- 238000000034 method Methods 0.000 claims abstract description 78
- 239000003054 catalyst Substances 0.000 claims abstract description 70
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 66
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 61
- 239000000047 product Substances 0.000 claims description 42
- -1 C 1 -C 6 alkyl Chemical group 0.000 claims description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 35
- 239000000203 mixture Substances 0.000 claims description 31
- 239000012452 mother liquor Substances 0.000 claims description 29
- 150000001875 compounds Chemical class 0.000 claims description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 21
- 150000002367 halogens Chemical class 0.000 claims description 21
- 229910052799 carbon Inorganic materials 0.000 claims description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000003446 ligand Substances 0.000 claims description 18
- 125000004104 aryloxy group Chemical group 0.000 claims description 17
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 17
- 239000002904 solvent Substances 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 16
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 16
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 16
- 239000007795 chemical reaction product Substances 0.000 claims description 16
- 239000002244 precipitate Substances 0.000 claims description 16
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims description 15
- 125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims description 15
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 15
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 15
- 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims description 15
- 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims description 15
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims description 15
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 15
- 125000005110 aryl thio group Chemical group 0.000 claims description 15
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 15
- 125000005368 heteroarylthio group Chemical group 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 238000005191 phase separation Methods 0.000 claims description 11
- 238000005406 washing Methods 0.000 claims description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 8
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 8
- 239000000376 reactant Substances 0.000 claims description 7
- GDJCQSNQOHRAGY-UHFFFAOYSA-N (4-chloro-2-fluoro-3-methoxyphenyl)boronic acid Chemical compound COC1=C(Cl)C=CC(B(O)O)=C1F GDJCQSNQOHRAGY-UHFFFAOYSA-N 0.000 claims description 6
- QOJNAEPFSUYAFL-UHFFFAOYSA-N 5,6-dichloropyridine-2-carboxylic acid Chemical compound OC(=O)C1=CC=C(Cl)C(Cl)=N1 QOJNAEPFSUYAFL-UHFFFAOYSA-N 0.000 claims description 6
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims description 5
- 239000000758 substrate Substances 0.000 claims description 5
- 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 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 4
- 239000000908 ammonium hydroxide Substances 0.000 claims description 4
- 238000004821 distillation Methods 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 239000007790 solid phase Substances 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 230000001172 regenerating effect Effects 0.000 claims description 3
- LHGHJAGVMNLDGA-UHFFFAOYSA-N 4,5,6-trichloropyridine-2-carboxylic acid Chemical compound OC(=O)C1=CC(Cl)=C(Cl)C(Cl)=N1 LHGHJAGVMNLDGA-UHFFFAOYSA-N 0.000 claims description 2
- 239000003880 polar aprotic solvent Substances 0.000 claims 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- 238000009825 accumulation Methods 0.000 claims 1
- 150000001642 boronic acid derivatives Chemical class 0.000 claims 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 claims 1
- 238000001179 sorption measurement Methods 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 34
- 239000010410 layer Substances 0.000 description 30
- 239000000243 solution Substances 0.000 description 29
- 239000002585 base Substances 0.000 description 24
- 239000007787 solid Substances 0.000 description 21
- 229910052757 nitrogen Inorganic materials 0.000 description 17
- 239000000654 additive Substances 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 16
- 239000012071 phase Substances 0.000 description 15
- 230000020477 pH reduction Effects 0.000 description 13
- PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 description 10
- 239000000460 chlorine Substances 0.000 description 9
- 238000005859 coupling reaction Methods 0.000 description 9
- 238000007792 addition Methods 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- 238000002955 isolation Methods 0.000 description 8
- 230000000996 additive effect Effects 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 6
- 238000004811 liquid chromatography Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000004064 recycling Methods 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 239000000010 aprotic solvent Substances 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 230000008929 regeneration Effects 0.000 description 4
- 238000011069 regeneration method Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 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 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- ULVPJKKERHMKLS-UHFFFAOYSA-N 1-chloro-4-fluoro-2-methoxybenzene Chemical compound COC1=CC(F)=CC=C1Cl ULVPJKKERHMKLS-UHFFFAOYSA-N 0.000 description 2
- ZAYTUZJMFVYJSU-UHFFFAOYSA-N 4,5-dichloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylic acid Chemical compound COC1=C(Cl)C=CC(C=2C(=C(Cl)C=C(N=2)C(O)=O)Cl)=C1F ZAYTUZJMFVYJSU-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-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
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- PZJSZBJLOWMDRG-UHFFFAOYSA-N furan-2-ylboronic acid Chemical compound OB(O)C1=CC=CO1 PZJSZBJLOWMDRG-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical group COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- UGOMMVLRQDMAQQ-UHFFFAOYSA-N xphos Chemical group CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 UGOMMVLRQDMAQQ-UHFFFAOYSA-N 0.000 description 2
- JCKZNMSBFBPDPM-UHFFFAOYSA-N (2-fluoro-3-methoxyphenyl)boronic acid Chemical compound COC1=CC=CC(B(O)O)=C1F JCKZNMSBFBPDPM-UHFFFAOYSA-N 0.000 description 1
- KYLUAQBYONVMCP-UHFFFAOYSA-N (2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P KYLUAQBYONVMCP-UHFFFAOYSA-N 0.000 description 1
- CAYQIZIAYYNFCS-UHFFFAOYSA-N (4-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Cl)C=C1 CAYQIZIAYYNFCS-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- GWEWQKZABZXLJH-UHFFFAOYSA-N 2-(furan-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=CO1 GWEWQKZABZXLJH-UHFFFAOYSA-N 0.000 description 1
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 1
- SHEHNNGFPKXFLB-UHFFFAOYSA-N 3,4-dichloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylic acid Chemical compound COC1=C(C=CC(=C1F)C2=NC(=C(C(=C2)Cl)Cl)C(=O)O)Cl SHEHNNGFPKXFLB-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- TUXYZHVUPGXXQG-UHFFFAOYSA-N 4-bromobenzoic acid Chemical compound OC(=O)C1=CC=C(Br)C=C1 TUXYZHVUPGXXQG-UHFFFAOYSA-N 0.000 description 1
- RHPUJHQBPORFGV-UHFFFAOYSA-N 4-chloro-2-methylphenol Chemical compound CC1=CC(Cl)=CC=C1O RHPUJHQBPORFGV-UHFFFAOYSA-N 0.000 description 1
- KUADVZCSDWKXEU-UHFFFAOYSA-N 5-chloro-4,6-bis(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylic acid Chemical compound ClC=1C(=CC(=NC=1C1=C(C(=C(C=C1)Cl)OC)F)C(=O)O)C1=C(C(=C(C=C1)Cl)OC)F KUADVZCSDWKXEU-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 102000020897 Formins Human genes 0.000 description 1
- 108091022623 Formins Proteins 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- BZDNMSNFLZXRLY-UHFFFAOYSA-N [2-(diphenylphosphanylmethyl)phenyl]methyl-diphenylphosphane Chemical compound C=1C=CC=C(CP(C=2C=CC=CC=2)C=2C=CC=CC=2)C=1CP(C=1C=CC=CC=1)C1=CC=CC=C1 BZDNMSNFLZXRLY-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- PDQHULYNICIFDN-UHFFFAOYSA-N benzyl 3,4,5,6-tetrachloropyridine-2-carboxylate Chemical compound ClC=1C(=NC(=C(C=1Cl)Cl)Cl)C(=O)OCC1=CC=CC=C1 PDQHULYNICIFDN-UHFFFAOYSA-N 0.000 description 1
- JOEXBHMEKNPAHP-UHFFFAOYSA-N benzyl 4-amino-3,5,6-trichloropyridine-2-carboxylate Chemical compound NC1=C(Cl)C(Cl)=NC(C(=O)OCC=2C=CC=CC=2)=C1Cl JOEXBHMEKNPAHP-UHFFFAOYSA-N 0.000 description 1
- SBSMNDZSCZNWKC-UHFFFAOYSA-N benzyl 5,6-dichloropyridine-2-carboxylate Chemical compound ClC=1C=CC(=NC=1Cl)C(=O)OCC1=CC=CC=C1 SBSMNDZSCZNWKC-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 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 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 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 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 125000000262 haloalkenyl group Chemical group 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- RYIFDLNTADZCRH-UHFFFAOYSA-N methyl 3,4,5,6-tetrachloropyridine-2-carboxylate Chemical compound COC(=O)C1=NC(Cl)=C(Cl)C(Cl)=C1Cl RYIFDLNTADZCRH-UHFFFAOYSA-N 0.000 description 1
- HVVBBQRGDOCRCA-UHFFFAOYSA-N methyl 5,6-dichloropyridine-2-carboxylate Chemical compound COC(=O)C1=CC=C(Cl)C(Cl)=N1 HVVBBQRGDOCRCA-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000000479 mixture part Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 229940081066 picolinic acid Drugs 0.000 description 1
- LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000005495 pyridazyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/803—Processes of preparation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2282—Unsaturated compounds used as ligands
- B01J31/2295—Cyclic compounds, e.g. cyclopentadienyls
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/40—Regeneration or reactivation
- B01J31/4015—Regeneration or reactivation of catalysts containing metals
- B01J31/4023—Regeneration or reactivation of catalysts containing metals containing iron group metals, noble metals or copper
- B01J31/4038—Regeneration or reactivation of catalysts containing metals containing iron group metals, noble metals or copper containing noble metals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
- B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
- B01J2231/4205—C-C cross-coupling, e.g. metal catalyzed or Friedel-Crafts type
- B01J2231/4211—Suzuki-type, i.e. RY + R'B(OR)2, in which R, R' are optionally substituted alkyl, alkenyl, aryl, acyl and Y is the leaving group
- B01J2231/4227—Suzuki-type, i.e. RY + R'B(OR)2, in which R, R' are optionally substituted alkyl, alkenyl, aryl, acyl and Y is the leaving group with Y= Cl
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/824—Palladium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/04—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing carboxylic acids or their salts
-
- 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
- Y02P20/582—Recycling of unreacted starting or intermediate materials
-
- 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
- Y02P20/584—Recycling of catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Separation, Recovery Or Treatment Of Waste Materials Containing Plastics (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562165502P | 2015-05-22 | 2015-05-22 | |
| US62/165,502 | 2015-05-22 | ||
| PCT/US2016/033429 WO2016191245A1 (en) | 2015-05-22 | 2016-05-20 | Recovery and/or reuse of palladium catalyst after a suzuki coupling |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2018516843A true JP2018516843A (ja) | 2018-06-28 |
| JP2018516843A5 JP2018516843A5 (https=) | 2019-06-20 |
Family
ID=57325189
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017547544A Withdrawn JP2018516843A (ja) | 2015-05-22 | 2016-05-20 | Ｓｕｚｕｋｉカップリング後のパラジウムの回収及び／または再利用 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US20160340311A1 (https=) |
| EP (1) | EP3297436A4 (https=) |
| JP (1) | JP2018516843A (https=) |
| KR (1) | KR20180011050A (https=) |
| CN (1) | CN107426998A (https=) |
| AR (1) | AR104734A1 (https=) |
| BR (1) | BR112017019207A2 (https=) |
| CA (1) | CA2978972A1 (https=) |
| CO (1) | CO2017008865A2 (https=) |
| IL (1) | IL254346A (https=) |
| MX (1) | MX2017011447A (https=) |
| TW (1) | TW201718503A (https=) |
| WO (1) | WO2016191245A1 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2021070684A (ja) * | 2019-10-30 | 2021-05-06 | 東ソー株式会社 | ハロゲン化合物の製造方法 |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR112020018094A2 (pt) | 2018-03-08 | 2020-12-22 | Incyte Corporation | Compostos de aminopirazina diol como inibidores de pi3k-¿ |
| US11046658B2 (en) | 2018-07-02 | 2021-06-29 | Incyte Corporation | Aminopyrazine derivatives as PI3K-γ inhibitors |
| CN110041373A (zh) * | 2019-04-29 | 2019-07-23 | 江苏万年长药业有限公司 | 一种雷迪帕韦中间体制备过程中贵金属催化剂的回收方法 |
| KR102419596B1 (ko) | 2020-10-06 | 2022-07-08 | 김창기 | 팔라듐이 포함된 슬러지 회수 장치 |
| CN114921657A (zh) * | 2022-05-06 | 2022-08-19 | 浙江微通催化新材料有限公司 | 一种从含铯盐的废钯催化剂中回收铯和钯的方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3641076A (en) * | 1970-08-24 | 1972-02-08 | Union Oil Co | Catalyst recovery |
| US4791226A (en) * | 1983-06-23 | 1988-12-13 | Amoco Corporation | Catalyst and process for purification of crude terephthalic acid |
| AR037228A1 (es) * | 2001-07-30 | 2004-11-03 | Dow Agrosciences Llc | Compuestos del acido 6-(aril o heteroaril)-4-aminopicolinico, composicion herbicida que los comprende y metodo para controlar vegetacion no deseada |
| US20060258875A1 (en) * | 2005-05-10 | 2006-11-16 | Clementine Reyes | Methods for manufacturing supported nanocatalysts and methods for using supported nanocatalysts |
| FR2914867B1 (fr) * | 2007-04-16 | 2009-06-05 | Univ Haute Alsace Etablissemen | Procede de synthese de catalyseurs heterogenes au palladium, catalyseurs obtenus et utilisations de ces derniers. |
| WO2011020900A2 (en) * | 2009-08-21 | 2011-02-24 | Technische Universität Berlin | A process for preparing biaryl compounds in a suzuki type reaction allowing product isolation and catalyst recycling in one step |
| US8912339B2 (en) * | 2011-12-30 | 2014-12-16 | Dow Agrosciences, Llc. | Methods of forming 4-chloro-2-fluoro-3-substituted-phenylboronic acid pinacol esters and methods of using the same |
| EP2797890B1 (en) * | 2011-12-30 | 2016-10-05 | Dow AgroSciences LLC | Methods of producing methyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylate |
| US8703953B2 (en) * | 2012-03-09 | 2014-04-22 | Bristol-Myers Squibb Company | Aryl ether-base kinase inhibitors |
-
2016
- 2016-05-20 US US15/159,973 patent/US20160340311A1/en not_active Abandoned
- 2016-05-20 WO PCT/US2016/033429 patent/WO2016191245A1/en not_active Ceased
- 2016-05-20 JP JP2017547544A patent/JP2018516843A/ja not_active Withdrawn
- 2016-05-20 MX MX2017011447A patent/MX2017011447A/es unknown
- 2016-05-20 EP EP16800528.8A patent/EP3297436A4/en not_active Withdrawn
- 2016-05-20 CA CA2978972A patent/CA2978972A1/en not_active Abandoned
- 2016-05-20 BR BR112017019207A patent/BR112017019207A2/pt not_active Application Discontinuation
- 2016-05-20 CN CN201680014261.6A patent/CN107426998A/zh active Pending
- 2016-05-20 KR KR1020177025293A patent/KR20180011050A/ko not_active Withdrawn
- 2016-05-23 AR ARP160101498A patent/AR104734A1/es unknown
- 2016-05-23 TW TW105115960A patent/TW201718503A/zh unknown
-
2017
- 2017-08-30 CO CONC2017/0008865A patent/CO2017008865A2/es unknown
- 2017-09-06 IL IL254346A patent/IL254346A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2021070684A (ja) * | 2019-10-30 | 2021-05-06 | 東ソー株式会社 | ハロゲン化合物の製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| TW201718503A (zh) | 2017-06-01 |
| EP3297436A4 (en) | 2018-12-26 |
| CA2978972A1 (en) | 2016-12-01 |
| US20160340311A1 (en) | 2016-11-24 |
| MX2017011447A (es) | 2018-06-18 |
| KR20180011050A (ko) | 2018-01-31 |
| CN107426998A (zh) | 2017-12-01 |
| WO2016191245A1 (en) | 2016-12-01 |
| IL254346A (en) | 2018-04-30 |
| CO2017008865A2 (es) | 2017-11-21 |
| EP3297436A1 (en) | 2018-03-28 |
| BR112017019207A2 (pt) | 2018-04-24 |
| AR104734A1 (es) | 2017-08-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2018516843A (ja) | Ｓｕｚｕｋｉカップリング後のパラジウムの回収及び／または再利用 | |
| Kobayashi et al. | Solvent-induced polymorphism of three-dimensional hydrogen-bonded networks of hexakis (4-carbamoylphenyl) benzene | |
| WO2012122746A1 (zh) | 一种2，3-二氯吡啶的制备方法 | |
| JP2018516843A5 (https=) | ||
| CN119137096A (zh) | 三氟甲磺酰化剂组合物、以及三氟甲磺酰氧基化合物或三氟甲磺酰化合物的制造方法 | |
| CN103880762B (zh) | 一种1,2,3-三氮唑类化合物的制备方法 | |
| CN106431979B (zh) | 一种2-硝基-4-三氟甲基苯腈的制备方法 | |
| CN103435610B (zh) | 一种咪唑并[1,2-a]吡啶类化合物的制备方法 | |
| US20120130071A1 (en) | Method for oxidizing methane | |
| CN102757390B (zh) | 一种制备2-甲氧基-4-肼基-5-氟嘧啶的方法 | |
| Kaur et al. | Ionic liquid assisted CC bond formation | |
| JP6336579B2 (ja) | ピリジン又はピラジン含有化合物 | |
| CN103483250B (zh) | 一种5-氨甲基烟酸的制备方法 | |
| JP5936511B2 (ja) | ３，３’−ジニトロ−４，４’−ジヒドロキシジフェニルエーテルの精製方法および３，３’−ジニトロ−４，４’−ジヒドロキシジフェニルエーテルの製造方法 | |
| CN107011218B (zh) | 一种氟氮型胺化试剂、其制备方法和应用 | |
| JP2012193124A (ja) | ２，３−ジクロロピリジンの製造方法 | |
| Zhang et al. | Recent Advances in the Synthesis of Nitrile Compounds Utilizing K4 [Fe (CN) 6]: Mechanistic Studies and Applications | |
| CN110563659B (zh) | 非均相铜催化一锅制备1,2,3-三唑类化合物的方法 | |
| CN108383779B (zh) | 一种3′-芳基-2,2′-联吡啶-6-甲酰胺衍生物的制备方法 | |
| JP2012097082A (ja) | 置換または非置換のトリフルオロメチル化アリールおよびヘテロアリール化合物を製造するための銅触媒による方法 | |
| JP4590049B2 (ja) | ベンゾ［ｂ］チオフェン誘導体の製造方法 | |
| CN103864645B (zh) | 一种二取代全氟烷基邻苯二甲腈化合物及其制备方法 | |
| JP4570057B2 (ja) | アリールピリジン誘導体の製造法 | |
| CN116693448B (zh) | 吲哚酰胺配体在碳氮偶联反应中的应用 | |
| US20140170058A1 (en) | Process for the removal of palladium from 4-amino-3-halo-5-fluoro-6-(aryl) pyridine-2-carboxylates and 4-amino-3-halo-6-(aryl)pyridine-2-carboxylates |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20190517 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20190517 |
|
| A761 | Written withdrawal of application |
Free format text: JAPANESE INTERMEDIATE CODE: A761 Effective date: 20191224 |