CA3023935A1 - Synthesis of 6-aryl-4-aminopicolinates and 2-aryl-6-aminopyrimidine-4-carboxylates by direct suzuki coupling - Google Patents
Synthesis of 6-aryl-4-aminopicolinates and 2-aryl-6-aminopyrimidine-4-carboxylates by direct suzuki coupling Download PDFInfo
- Publication number
- CA3023935A1 CA3023935A1 CA3023935A CA3023935A CA3023935A1 CA 3023935 A1 CA3023935 A1 CA 3023935A1 CA 3023935 A CA3023935 A CA 3023935A CA 3023935 A CA3023935 A CA 3023935A CA 3023935 A1 CA3023935 A1 CA 3023935A1
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- Canada
- Prior art keywords
- catalyst
- alkyl
- aryl
- chloro
- suzuki coupling
- Prior art date
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- Pending
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- 238000006069 Suzuki reaction reaction Methods 0.000 title claims abstract description 46
- 238000003786 synthesis reaction Methods 0.000 title abstract description 9
- 230000015572 biosynthetic process Effects 0.000 title abstract description 8
- 238000000034 method Methods 0.000 claims abstract description 109
- 239000000203 mixture Substances 0.000 claims abstract description 61
- 239000003054 catalyst Substances 0.000 claims abstract description 60
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 16
- 239000002904 solvent Substances 0.000 claims abstract description 15
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 144
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 119
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 83
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 72
- 235000015320 potassium carbonate Nutrition 0.000 claims description 66
- 125000003118 aryl group Chemical group 0.000 claims description 54
- 150000001543 aryl boronic acids Chemical class 0.000 claims description 49
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 40
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 40
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical group [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims description 40
- 125000000217 alkyl group Chemical group 0.000 claims description 39
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- 229910052731 fluorine Inorganic materials 0.000 claims description 32
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 29
- 229910052801 chlorine Inorganic materials 0.000 claims description 25
- 229910052736 halogen Chemical group 0.000 claims description 25
- 150000002367 halogens Chemical group 0.000 claims description 24
- 150000005005 aminopyrimidines Chemical class 0.000 claims description 23
- 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 21
- 125000001188 haloalkyl group Chemical group 0.000 claims description 21
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 19
- 238000005859 coupling reaction Methods 0.000 claims description 19
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 17
- 150000003927 aminopyridines Chemical class 0.000 claims description 17
- 229910052763 palladium Inorganic materials 0.000 claims description 17
- 230000008878 coupling Effects 0.000 claims description 15
- 238000010168 coupling process Methods 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 claims description 14
- FRMBCYILCYTPHY-UHFFFAOYSA-N methyl 4-amino-3,6-dichloropyridine-2-carboxylate Chemical compound COC(=O)C1=NC(Cl)=CC(N)=C1Cl FRMBCYILCYTPHY-UHFFFAOYSA-N 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000002837 carbocyclic group Chemical group 0.000 claims description 8
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 7
- 239000012035 limiting reagent Substances 0.000 claims description 7
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical group [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 claims description 7
- 125000006273 (C1-C3) alkyl group Chemical class 0.000 claims description 6
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- LVOXVUFKRAUPQA-UHFFFAOYSA-N (4-chloro-2-fluoro-3-methoxyphenyl)-dimethoxyborane Chemical compound COB(OC)C1=CC=C(Cl)C(OC)=C1F LVOXVUFKRAUPQA-UHFFFAOYSA-N 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- YEUYMEGMXJWEDE-UHFFFAOYSA-N methyl 6-amino-2,5-dichloropyrimidine-4-carboxylate Chemical compound COC(=O)C1=NC(Cl)=NC(N)=C1Cl YEUYMEGMXJWEDE-UHFFFAOYSA-N 0.000 claims description 2
- VHXVXHHVPQJMFM-UHFFFAOYSA-N methyl 6-amino-2-chloro-5-methoxypyrimidine-4-carboxylate Chemical compound COC(=O)C1=NC(Cl)=NC(N)=C1OC VHXVXHHVPQJMFM-UHFFFAOYSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 4
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 2
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims 1
- WHKVMIKJUDLXNI-UHFFFAOYSA-N [7-fluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indol-1-yl]-tri(propan-2-yl)silane Chemical compound FC1=C2N([Si](C(C)C)(C(C)C)C(C)C)C=CC2=CC=C1B1OC(C)(C)C(C)(C)O1 WHKVMIKJUDLXNI-UHFFFAOYSA-N 0.000 claims 1
- -1 alkyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylates Chemical class 0.000 abstract description 114
- 238000010626 work up procedure Methods 0.000 abstract description 5
- 239000002994 raw material Substances 0.000 abstract description 3
- 230000002194 synthesizing effect Effects 0.000 abstract description 3
- 238000001311 chemical methods and process Methods 0.000 abstract 1
- 230000004048 modification Effects 0.000 abstract 1
- 238000012986 modification Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 86
- 239000000243 solution Substances 0.000 description 77
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 68
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 59
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
- 125000003545 alkoxy group Chemical group 0.000 description 31
- KDHKOPYYWOHESS-UHFFFAOYSA-N halauxifen-methyl Chemical compound NC1=C(Cl)C(C(=O)OC)=NC(C=2C(=C(OC)C(Cl)=CC=2)F)=C1 KDHKOPYYWOHESS-UHFFFAOYSA-N 0.000 description 30
- 229910052757 nitrogen Inorganic materials 0.000 description 29
- 125000001424 substituent group Chemical group 0.000 description 22
- 239000011541 reaction mixture Substances 0.000 description 21
- 239000002002 slurry Substances 0.000 description 19
- 239000012074 organic phase Substances 0.000 description 17
- 239000012071 phase Substances 0.000 description 17
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 14
- 125000004414 alkyl thio group Chemical group 0.000 description 13
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 12
- 239000011736 potassium bicarbonate Substances 0.000 description 12
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 12
- 125000004995 haloalkylthio group Chemical group 0.000 description 11
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 11
- 235000015497 potassium bicarbonate Nutrition 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 125000004093 cyano group Chemical group *C#N 0.000 description 8
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 7
- 125000006809 haloalkylaminocarbonyl group Chemical group 0.000 description 7
- 230000000717 retained effect Effects 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 6
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 description 6
- 239000001569 carbon dioxide Substances 0.000 description 6
- 229910002092 carbon dioxide Inorganic materials 0.000 description 6
- 238000010511 deprotection reaction Methods 0.000 description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- 125000004993 haloalkoxycarbonyl group Chemical group 0.000 description 6
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 description 6
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 description 6
- 238000011068 loading method Methods 0.000 description 6
- 230000007935 neutral effect Effects 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 235000011181 potassium carbonates Nutrition 0.000 description 6
- SSSUQLVGYOIGIX-UHFFFAOYSA-N 4-amino-6-chloropyridine-2-carboxylic acid Chemical class NC1=CC(Cl)=NC(C(O)=O)=C1 SSSUQLVGYOIGIX-UHFFFAOYSA-N 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 125000000304 alkynyl group Chemical group 0.000 description 5
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 description 5
- WNZCDFOXYNRBRB-UHFFFAOYSA-N florpyrauxifen-benzyl Chemical compound COC1=C(Cl)C=CC(C=2C(=C(N)C(Cl)=C(C(=O)OCC=3C=CC=CC=3)N=2)F)=C1F WNZCDFOXYNRBRB-UHFFFAOYSA-N 0.000 description 5
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 description 5
- 239000003446 ligand Substances 0.000 description 5
- WYQIQNYHZCSJQD-UHFFFAOYSA-N 4-amino-2-chloro-1H-pyridine-2-carboxylic acid Chemical compound NC1=CC(Cl)(NC=C1)C(O)=O WYQIQNYHZCSJQD-UHFFFAOYSA-N 0.000 description 4
- UHGBKWYISOUYAE-UHFFFAOYSA-N 6-amino-2-chloropyrimidine-4-carboxylic acid Chemical class NC1=CC(C(O)=O)=NC(Cl)=N1 UHGBKWYISOUYAE-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- CLQREWNDDSMAPG-UHFFFAOYSA-N methyl 6-amino-5-chloro-2-(4-chloro-2-fluoro-3-methoxyphenyl)pyrimidine-4-carboxylate Chemical compound NC1=C(Cl)C(C(=O)OC)=NC(C=2C(=C(OC)C(Cl)=CC=2)F)=N1 CLQREWNDDSMAPG-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 3
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003282 alkyl amino group Chemical group 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- ACKJTNJQCUUANK-UHFFFAOYSA-N benzyl 4-amino-3,6-dichloro-5-fluoropyridine-2-carboxylate Chemical compound NC1=C(C(=NC(=C1F)Cl)C(=O)OCC1=CC=CC=C1)Cl ACKJTNJQCUUANK-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- 239000011698 potassium fluoride Substances 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- 125000006017 1-propenyl group Chemical group 0.000 description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
- XONKJZDHGCMRRF-UHFFFAOYSA-N 7-fluoro-1h-indole Chemical group FC1=CC=CC2=C1NC=C2 XONKJZDHGCMRRF-UHFFFAOYSA-N 0.000 description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000021736 acetylation Effects 0.000 description 2
- 238000006640 acetylation reaction Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
- 230000006196 deacetylation Effects 0.000 description 2
- 238000003381 deacetylation reaction Methods 0.000 description 2
- 229940043279 diisopropylamine Drugs 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 125000004992 haloalkylamino group Chemical group 0.000 description 2
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- KIKNEFFJHGIUKZ-UHFFFAOYSA-N methyl 4-amino-3,6-dichloro-5-fluoropyridine-2-carboxylate Chemical compound COC(=O)C1=NC(Cl)=C(F)C(N)=C1Cl KIKNEFFJHGIUKZ-UHFFFAOYSA-N 0.000 description 2
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 2
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 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
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 2
- 125000006823 (C1-C6) acyl group Chemical group 0.000 description 1
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 1
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 description 1
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 description 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 1
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 description 1
- 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 description 1
- 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 description 1
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 description 1
- 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 description 1
- FIARMZDBEGVMLV-UHFFFAOYSA-N 1,1,2,2,2-pentafluoroethanolate Chemical group [O-]C(F)(F)C(F)(F)F FIARMZDBEGVMLV-UHFFFAOYSA-N 0.000 description 1
- 125000005919 1,2,2-trimethylpropyl group Chemical group 0.000 description 1
- 125000005918 1,2-dimethylbutyl group Chemical group 0.000 description 1
- 125000006083 1-bromoethyl group Chemical group 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
- 125000001478 1-chloroethyl group Chemical group [H]C([H])([H])C([H])(Cl)* 0.000 description 1
- 125000006074 1-ethyl-2-butenyl group Chemical group 0.000 description 1
- 125000006082 1-ethyl-2-methyl-2-propenyl group Chemical group 0.000 description 1
- 125000004736 1-ethyl-2-methylpropylthio group Chemical group C(C)C(C(C)C)S* 0.000 description 1
- 125000006075 1-ethyl-3-butenyl group Chemical group 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004776 1-fluoroethyl group Chemical group [H]C([H])([H])C([H])(F)* 0.000 description 1
- 125000006039 1-hexenyl group Chemical group 0.000 description 1
- 125000006025 1-methyl-1-butenyl group Chemical group 0.000 description 1
- 125000006028 1-methyl-2-butenyl group Chemical group 0.000 description 1
- 125000006048 1-methyl-2-pentenyl group Chemical group 0.000 description 1
- 125000006030 1-methyl-3-butenyl group Chemical group 0.000 description 1
- 125000006052 1-methyl-3-pentenyl group Chemical group 0.000 description 1
- 125000006055 1-methyl-4-pentenyl group Chemical group 0.000 description 1
- 125000006018 1-methyl-ethenyl group Chemical group 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 125000004781 2,2-dichloro-2-fluoroethyl group Chemical group [H]C([H])(*)C(F)(Cl)Cl 0.000 description 1
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- 125000004780 2-chloro-2,2-difluoroethyl group Chemical group [H]C([H])(*)C(F)(F)Cl 0.000 description 1
- 125000004779 2-chloro-2-fluoroethyl group Chemical group [H]C([H])(*)C([H])(F)Cl 0.000 description 1
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- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- JRZBTJVSAANBEV-UHFFFAOYSA-N 4-aminopyridine-2-carboxylic acid Chemical compound NC1=CC=NC(C(O)=O)=C1 JRZBTJVSAANBEV-UHFFFAOYSA-N 0.000 description 1
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- 125000003119 4-methyl-3-pentenyl group Chemical group [H]\C(=C(/C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006058 4-methyl-4-pentenyl group Chemical group 0.000 description 1
- 125000006043 5-hexenyl group Chemical group 0.000 description 1
- KXPKWHNZKVLCRR-UHFFFAOYSA-N 6-aminopyrimidine-4-carboxylic acid Chemical compound NC1=CC(C(O)=O)=NC=N1 KXPKWHNZKVLCRR-UHFFFAOYSA-N 0.000 description 1
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- 239000004135 Bone phosphate Substances 0.000 description 1
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 description 1
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- 125000000041 C6-C10 aryl group Chemical group 0.000 description 1
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- NIXXQNOQHKNPEJ-UHFFFAOYSA-N aminopyralid Chemical compound NC1=CC(Cl)=NC(C(O)=O)=C1Cl NIXXQNOQHKNPEJ-UHFFFAOYSA-N 0.000 description 1
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- 125000005997 bromomethyl group Chemical group 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 description 1
- 125000004773 chlorofluoromethyl group Chemical group [H]C(F)(Cl)* 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 208000012839 conversion disease Diseases 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 description 1
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
- VPLLTGLLUHLIHA-UHFFFAOYSA-N dicyclohexyl(phenyl)phosphane Chemical compound C1CCCCC1P(C=1C=CC=CC=1)C1CCCCC1 VPLLTGLLUHLIHA-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- UQGFMSUEHSUPRD-UHFFFAOYSA-N disodium;3,7-dioxido-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane Chemical compound [Na+].[Na+].O1B([O-])OB2OB([O-])OB1O2 UQGFMSUEHSUPRD-UHFFFAOYSA-N 0.000 description 1
- XOJNEFQLMRCOMS-UHFFFAOYSA-N ditert-butyl(phenyl)phosphane Chemical compound CC(C)(C)P(C(C)(C)C)C1=CC=CC=C1 XOJNEFQLMRCOMS-UHFFFAOYSA-N 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 125000005553 heteroaryloxy group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000003116 impacting effect Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
- PZSVMKWRONODDG-UHFFFAOYSA-N methyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylate Chemical compound NC1=C(Cl)C(C(=O)OC)=NC(C=2C(=C(OC)C(Cl)=CC=2)F)=C1F PZSVMKWRONODDG-UHFFFAOYSA-N 0.000 description 1
- VBJWNAVKBPJKEH-UHFFFAOYSA-N methyl 6-amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-methoxypyrimidine-4-carboxylate Chemical compound NC1=C(OC)C(C(=O)OC)=NC(C=2C(=C(OC)C(Cl)=CC=2)F)=N1 VBJWNAVKBPJKEH-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-M picolinate Chemical compound [O-]C(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-M 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 125000006238 prop-1-en-1-yl group Chemical group [H]\C(*)=C(/[H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 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
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000011182 sodium carbonates Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- NTUROZDXWLPVHB-UHFFFAOYSA-M sodium;3-diphenylphosphanylbenzenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NTUROZDXWLPVHB-UHFFFAOYSA-M 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000003107 substituted aryl group Chemical group 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
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- WXAZIUYTQHYBFW-UHFFFAOYSA-N tris(4-methylphenyl)phosphane Chemical compound C1=CC(C)=CC=C1P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 WXAZIUYTQHYBFW-UHFFFAOYSA-N 0.000 description 1
- 238000010977 unit operation Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
-
- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/30—Catalysts, in general, characterised by their form or physical properties characterised by their physical properties
- B01J35/391—Physical properties of the active metal ingredient
-
- 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
-
- 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
- C07D213/90—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 more than three double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662338562P | 2016-05-19 | 2016-05-19 | |
| US62/338562 | 2016-05-19 | ||
| US201662416811P | 2016-11-03 | 2016-11-03 | |
| US62/416811 | 2016-11-03 | ||
| PCT/US2017/033489 WO2017201377A1 (en) | 2016-05-19 | 2017-05-19 | Synthesis of 6-aryl-4-aminopicolinates and 2-aryl-6-aminopyrimidine-4-carboxylates by direct suzuki coupling |
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| BR112018073348B8 (pt) * | 2016-05-19 | 2023-05-16 | Dow Agrosciences Llc | Métodos para preparar 6-aril-4-aminopicolinatos e 2-aril-6-aminopirimidina-4-carboxilatos por acoplamento direto de suzuki |
| CN113015721B (zh) * | 2018-09-19 | 2025-07-25 | 科迪华农业科技有限责任公司 | 毒莠定卤素类似物的制备 |
| WO2020133403A1 (zh) * | 2018-12-29 | 2020-07-02 | 青岛清原化合物有限公司 | 取代的嘧啶芳酯衍生物及其制备方法、除草组合物和应用 |
| US20230357155A1 (en) * | 2020-03-18 | 2023-11-09 | Corteva Agriscience Llc | Improved synthesis of 4-amino-6-(heterocyclic)picolinates |
| US20230174490A1 (en) | 2020-03-18 | 2023-06-08 | Corteva Agriscience Llc | Improved synthesis of 6-aryl-4-aminopicolinates |
| US20230167061A1 (en) * | 2020-05-11 | 2023-06-01 | Corteva Agriscience Llc | Preparation of compounds having pesticidal activity |
| WO2023248174A1 (en) * | 2022-06-22 | 2023-12-28 | Hetero Labs Limited | An improved process for preparation of voxelotor |
| CN115819334B (zh) * | 2022-06-28 | 2025-03-18 | 安徽众邦生物工程有限公司 | 一种氯氟吡啶酯的制备方法 |
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| 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 |
| TWI396505B (zh) * | 2006-01-13 | 2013-05-21 | Dow Agrosciences Llc | ２-（聚-經取代芳基）-６-胺-５-鹵-４-嘧啶羧酸及其作為除草劑之用途 |
| BRPI0815349A2 (pt) * | 2007-08-13 | 2015-02-10 | Dow Agrosciences Llc | 6-amino-5-cloro-4-pirimidinacarboxilatos substituídos com 2-(2-fluorofeni-la) e seu uso como herbicidas |
| EP2181098B1 (en) * | 2007-08-30 | 2011-03-02 | Dow AgroSciences LLC | 2-(substituted phenyl)-6-amino-5-alkoxy, thioalkoxy and aminoalkyl-4-pyrimidinecarboxylates and their use as herbicides |
| CN101883759B (zh) | 2007-10-02 | 2014-05-21 | 陶氏益农公司 | 2-取代的-6-氨基-5-烷基、烯基或炔基-嘧啶-4-羧酸和6-取代的-4-氨基-3-烷基、烯基或炔基吡啶-2-羧酸以及它们作为除草剂的用途 |
| JP5314126B2 (ja) * | 2008-04-18 | 2013-10-16 | ダウ アグロサイエンシィズ エルエルシー | ２−（置換フェニル）−６−ヒドロキシ又はアルコキシ−５−置換−４−ピリミジンカルボキシラート及び除草剤としてのそれらの使用 |
| GB0808664D0 (en) * | 2008-05-13 | 2008-06-18 | Syngenta Ltd | Chemical compounds |
| GB0902474D0 (en) * | 2009-02-13 | 2009-04-01 | Syngenta Ltd | Chemical compounds |
| GB0907625D0 (en) * | 2009-05-01 | 2009-06-10 | Syngenta Ltd | Method of controlling undesired vegetation |
| TWI529163B (zh) * | 2011-01-25 | 2016-04-11 | 陶氏農業科學公司 | 用於製備４－胺基－５－氟－３－鹵素－６－（經取代之）吡啶甲酸酯的方法 |
| TWI520943B (zh) * | 2011-01-25 | 2016-02-11 | 陶氏農業科學公司 | 用於製備４－胺基－３－氯－５－氟－６－（經取代的）吡啶甲酸酯的方法（二） |
| TWI592401B (zh) * | 2011-01-25 | 2017-07-21 | 陶氏農業科學公司 | 用於製備４－胺基－３－氯－５－氟－６－（經取代的）吡啶甲酸酯的方法（一） |
| RU2556000C2 (ru) | 2011-01-25 | 2015-07-10 | ДАУ АГРОСАЙЕНСИЗ ЭлЭлСи | 6-амино-2-замещенные-5- винилсилилпиримидин-4-карбоновые кислоты и сложные эфиры и 4-амино-6-замещенные-3-винилсилилпиридин-пиколиновые кислоты и сложные эфиры как гербициды |
| MX370455B (es) * | 2011-07-27 | 2019-12-13 | Bayer Ip Gmbh | Ácidos picolínicos y piridimin-4-carboxílicos sustituidos, procedimiento para su preparación y su uso como herbicidas y reguladores del crecimiento de plantas. |
| US8754110B2 (en) * | 2011-12-30 | 2014-06-17 | Dow Agrosciences, Llc. | Methods of producing methyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylate |
| KR102065950B1 (ko) * | 2011-12-30 | 2020-01-14 | 다우 아그로사이언시즈 엘엘씨 | (4-클로로-2-플루오로-3-치환된-페닐) 보로네이트의 단리 방법 및 그의 사용 방법 |
| AR091856A1 (es) * | 2012-07-24 | 2015-03-04 | Dow Agrosciences Llc | Proceso para la preparacion de 4-amino-5-fluor-3-halo-6-(substituido) picolinatos |
| CN102875456B (zh) * | 2012-10-23 | 2013-12-11 | 西华大学 | 3,6-二氯-2-氨基吡啶的化学合成方法 |
| US20140170058A1 (en) * | 2012-12-13 | 2014-06-19 | Dow Agrosciences Llc | 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 |
| ES2811084T3 (es) | 2013-03-15 | 2021-03-10 | Dow Agrosciences Llc | 4-Amino-6-(heterociclil)picolinatos y 6-amino-2-(heterociclil)pirimidina-4-carbililatos y su uso como herbicidas |
| US9637505B2 (en) | 2013-03-15 | 2017-05-02 | Dow Agrosciences Llc | 4-amino-6-(heterocyclic)picolinates and 6-amino-2-(heterocyclic)pyrimidine-4-carboxylates and their use as herbicides |
| RU2672584C2 (ru) * | 2013-03-15 | 2018-11-16 | ДАУ АГРОСАЙЕНСИЗ ЭлЭлСи | 4-амино-6-(гетероциклил)пиколинаты и 6-амино-2-(гетероциклил)пиримидин-4-карбоксилаты и их применение в качестве гербицидов |
| HUE041698T2 (hu) * | 2013-03-15 | 2019-05-28 | Dow Agrosciences Llc | Új 4-aminopiridin- és 6-aminopririmidin-karboxilátok mint herbicidek |
| US9113629B2 (en) * | 2013-03-15 | 2015-08-25 | Dow Agrosciences Llc | 4-amino-6-(4-substituted-phenyl)-picolinates and 6-amino-2-(4-substituted-phenyl)-pyrimidine-4-carboxylates and their use as herbicides |
| BR112018073348B8 (pt) * | 2016-05-19 | 2023-05-16 | Dow Agrosciences Llc | Métodos para preparar 6-aril-4-aminopicolinatos e 2-aril-6-aminopirimidina-4-carboxilatos por acoplamento direto de suzuki |
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- 2017-05-19 RU RU2018144344A patent/RU2018144344A/ru unknown
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- 2017-05-19 CA CA3023935A patent/CA3023935A1/en active Pending
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| IL263075A (en) | 2018-12-31 |
| BR112018073348B1 (pt) | 2023-01-24 |
| US10570114B2 (en) | 2020-02-25 |
| AU2017268424A1 (en) | 2018-11-22 |
| US20180334444A1 (en) | 2018-11-22 |
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| US20180334445A1 (en) | 2018-11-22 |
| RU2018144344A (ru) | 2020-06-19 |
| JP2019516708A (ja) | 2019-06-20 |
| WO2017201377A1 (en) | 2017-11-23 |
| US10544121B2 (en) | 2020-01-28 |
| BR112018073348A2 (pt) | 2019-03-06 |
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| EP3458442B1 (en) | 2022-12-28 |
| US10087164B2 (en) | 2018-10-02 |
| RU2018144344A3 (enExample) | 2021-02-18 |
| AU2021203233A1 (en) | 2021-06-10 |
| MX2018014174A (es) | 2019-03-14 |
| JP2022141912A (ja) | 2022-09-29 |
| BR112018073348B8 (pt) | 2023-05-16 |
| NZ747932A (en) | 2022-03-25 |
| KR20190007048A (ko) | 2019-01-21 |
| EP3458442A4 (en) | 2020-04-22 |
| AU2017268424B2 (en) | 2021-07-15 |
| US20170334878A1 (en) | 2017-11-23 |
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