RU2632203C2 - Способ получения 4-амино-5-фтор-3-галоген-6-(замещенных)пиколинатов - Google Patents
Способ получения 4-амино-5-фтор-3-галоген-6-(замещенных)пиколинатов Download PDFInfo
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- RU2632203C2 RU2632203C2 RU2015106019A RU2015106019A RU2632203C2 RU 2632203 C2 RU2632203 C2 RU 2632203C2 RU 2015106019 A RU2015106019 A RU 2015106019A RU 2015106019 A RU2015106019 A RU 2015106019A RU 2632203 C2 RU2632203 C2 RU 2632203C2
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- Prior art keywords
- formula
- compound
- alkyl
- give
- halogen
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- 238000004519 manufacturing process Methods 0.000 title abstract description 21
- 150000001875 compounds Chemical class 0.000 claims abstract description 340
- 238000006243 chemical reaction Methods 0.000 claims abstract description 96
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 76
- 150000002367 halogens Chemical class 0.000 claims abstract description 64
- 230000009466 transformation Effects 0.000 claims abstract description 62
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 60
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 44
- 125000001424 substituent group Chemical group 0.000 claims abstract description 43
- 150000003839 salts Chemical class 0.000 claims abstract description 42
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 41
- 239000003054 catalyst Substances 0.000 claims abstract description 40
- 239000001257 hydrogen Substances 0.000 claims abstract description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 38
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims abstract description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 25
- 230000002140 halogenating effect Effects 0.000 claims abstract description 24
- 229910052802 copper Inorganic materials 0.000 claims abstract description 23
- 239000010949 copper Substances 0.000 claims abstract description 23
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 22
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 22
- 229910052723 transition metal Inorganic materials 0.000 claims abstract description 22
- 150000003624 transition metals Chemical class 0.000 claims abstract description 22
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000005977 Ethylene Substances 0.000 claims abstract description 21
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims abstract description 21
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 21
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 17
- 125000003277 amino group Chemical group 0.000 claims abstract description 14
- 238000000844 transformation Methods 0.000 claims abstract description 6
- -1 phosphonium halide Chemical class 0.000 claims description 87
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 85
- 238000000034 method Methods 0.000 claims description 53
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 52
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 42
- 238000009833 condensation Methods 0.000 claims description 31
- 230000005494 condensation Effects 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 239000002904 solvent Substances 0.000 claims description 28
- 229910021529 ammonia Inorganic materials 0.000 claims description 25
- 238000003682 fluorination reaction Methods 0.000 claims description 25
- 238000005576 amination reaction Methods 0.000 claims description 22
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 21
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 claims description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 11
- 239000011698 potassium fluoride Substances 0.000 claims description 11
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 11
- 150000001412 amines Chemical class 0.000 claims description 10
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 9
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 9
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 7
- 230000015572 biosynthetic process Effects 0.000 claims description 7
- 150000003983 crown ethers Chemical class 0.000 claims description 6
- 235000003270 potassium fluoride Nutrition 0.000 claims description 6
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical group [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 claims description 5
- 238000000605 extraction Methods 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- 238000001953 recrystallisation Methods 0.000 claims description 4
- 229920000728 polyester Polymers 0.000 claims description 3
- 230000007935 neutral effect Effects 0.000 claims description 2
- 238000001556 precipitation Methods 0.000 claims description 2
- 230000005588 protonation Effects 0.000 claims description 2
- 239000011775 sodium fluoride Substances 0.000 claims description 2
- 235000013024 sodium fluoride Nutrition 0.000 claims description 2
- 229910001512 metal fluoride Inorganic materials 0.000 claims 3
- 150000003990 18-crown-6 derivatives Chemical group 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 230000003472 neutralizing effect Effects 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 11
- 230000000694 effects Effects 0.000 abstract description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 abstract 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- 229910003204 NH2 Inorganic materials 0.000 abstract 1
- 238000005481 NMR spectroscopy Methods 0.000 description 78
- 239000000460 chlorine Substances 0.000 description 61
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 60
- 239000011541 reaction mixture Substances 0.000 description 54
- 239000000203 mixture Substances 0.000 description 50
- 239000007787 solid Substances 0.000 description 47
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- 239000000047 product Substances 0.000 description 26
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 description 22
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 239000012453 solvate Substances 0.000 description 21
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 description 18
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 18
- 238000004949 mass spectrometry Methods 0.000 description 18
- 229910052757 nitrogen Inorganic materials 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 16
- 235000019439 ethyl acetate Nutrition 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- 239000000741 silica gel Substances 0.000 description 14
- 229910002027 silica gel Inorganic materials 0.000 description 14
- 238000003756 stirring Methods 0.000 description 14
- 239000003153 chemical reaction reagent Substances 0.000 description 13
- 125000005843 halogen group Chemical group 0.000 description 13
- 238000004128 high performance liquid chromatography Methods 0.000 description 13
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 238000004458 analytical method Methods 0.000 description 12
- 125000001153 fluoro group Chemical group F* 0.000 description 12
- 239000000725 suspension Substances 0.000 description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 11
- 125000006239 protecting group Chemical group 0.000 description 11
- 239000007858 starting material Substances 0.000 description 11
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 10
- 238000006482 condensation reaction Methods 0.000 description 10
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
- 238000004821 distillation Methods 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 239000012442 inert solvent Substances 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 7
- 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 7
- 235000017168 chlorine Nutrition 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 7
- 239000000543 intermediate Substances 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 238000002451 electron ionisation mass spectrometry Methods 0.000 description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- MUCAKBKIVUFYQH-UHFFFAOYSA-N propan-2-yl 4,5,6-trichloropyridine-2-carboxylate Chemical compound CC(C)OC(=O)C1=CC(Cl)=C(Cl)C(Cl)=N1 MUCAKBKIVUFYQH-UHFFFAOYSA-N 0.000 description 6
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- 238000005658 halogenation reaction Methods 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- PJAIMBYNTXNOCN-UHFFFAOYSA-N 3,6-dibromo-1h-indole Chemical compound BrC1=CC=C2C(Br)=CNC2=C1 PJAIMBYNTXNOCN-UHFFFAOYSA-N 0.000 description 4
- ZAFLZRNJFHWOQQ-UHFFFAOYSA-N 3-chloropyridine-2-carbonyl chloride Chemical class ClC(=O)C1=NC=CC=C1Cl ZAFLZRNJFHWOQQ-UHFFFAOYSA-N 0.000 description 4
- LPLSXEQPNFWFFS-UHFFFAOYSA-N 4,5,6-trichloropyridine-2-carbonyl chloride Chemical compound ClC(=O)C1=CC(Cl)=C(Cl)C(Cl)=N1 LPLSXEQPNFWFFS-UHFFFAOYSA-N 0.000 description 4
- JRIASDXJZYOBCA-UHFFFAOYSA-N 5-chloropyridine-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=N1 JRIASDXJZYOBCA-UHFFFAOYSA-N 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000012320 chlorinating reagent Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 150000002148 esters Chemical group 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 230000026030 halogenation Effects 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000002808 molecular sieve Substances 0.000 description 4
- 238000012544 monitoring process Methods 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical class OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 4
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 4
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 4
- 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 4
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 3
- XTMUXJBJCMRWPG-UHFFFAOYSA-N 3-chloropyridine-2-carboxylic acid Chemical class OC(=O)C1=NC=CC=C1Cl XTMUXJBJCMRWPG-UHFFFAOYSA-N 0.000 description 3
- QERMRZQVBGYSFJ-UHFFFAOYSA-N 4,5,6-trifluoropyridine-2-carbonyl fluoride Chemical compound FC(=O)C1=CC(F)=C(F)C(F)=N1 QERMRZQVBGYSFJ-UHFFFAOYSA-N 0.000 description 3
- BASWDJWLHQQKAU-UHFFFAOYSA-N 4,5-dichloro-6-(4-chlorophenyl)pyridine-2-carbonyl chloride Chemical compound ClC(=O)C1=CC(Cl)=C(Cl)C(C=2C=CC(Cl)=CC=2)=N1 BASWDJWLHQQKAU-UHFFFAOYSA-N 0.000 description 3
- AHDFCMPBXDNBBR-UHFFFAOYSA-N 4,5-dichloro-6-(4-chlorophenyl)pyridine-2-carboxylic acid Chemical compound OC(=O)C1=CC(Cl)=C(Cl)C(C=2C=CC(Cl)=CC=2)=N1 AHDFCMPBXDNBBR-UHFFFAOYSA-N 0.000 description 3
- YRUPBIPDCOEFHZ-UHFFFAOYSA-N 4,5-dichloro-6-(4-methoxyphenyl)pyridine-2-carbonyl chloride Chemical compound C1=CC(OC)=CC=C1C1=NC(C(Cl)=O)=CC(Cl)=C1Cl YRUPBIPDCOEFHZ-UHFFFAOYSA-N 0.000 description 3
- BNQYSFWLVLAPPF-UHFFFAOYSA-N 4,5-dichloro-6-(4-methoxyphenyl)pyridine-2-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C1=NC(C(O)=O)=CC(Cl)=C1Cl BNQYSFWLVLAPPF-UHFFFAOYSA-N 0.000 description 3
- XQZXNWKQNTWHOZ-UHFFFAOYSA-N 4,5-dichloro-6-phenylpyridine-2-carbonyl chloride Chemical compound ClC(=O)C1=CC(Cl)=C(Cl)C(C=2C=CC=CC=2)=N1 XQZXNWKQNTWHOZ-UHFFFAOYSA-N 0.000 description 3
- HBPSHBLIEQWDMD-UHFFFAOYSA-N 4,5-dichloro-6-phenylpyridine-2-carboxylic acid Chemical compound OC(=O)C1=CC(Cl)=C(Cl)C(C=2C=CC=CC=2)=N1 HBPSHBLIEQWDMD-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- WAIPAZQMEIHHTJ-UHFFFAOYSA-N [Cr].[Co] Chemical compound [Cr].[Co] WAIPAZQMEIHHTJ-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 229910001515 alkali metal fluoride Inorganic materials 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 125000004104 aryloxy group Chemical group 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000005660 chlorination reaction Methods 0.000 description 3
- 238000010276 construction Methods 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- YDVNLQGCLLPHAH-UHFFFAOYSA-N dichloromethane;hydrate Chemical compound O.ClCCl YDVNLQGCLLPHAH-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 238000003818 flash chromatography Methods 0.000 description 3
- 239000004009 herbicide Substances 0.000 description 3
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 3
- 239000011630 iodine Chemical group 0.000 description 3
- DKCGUEHEVORRHJ-UHFFFAOYSA-N methyl 4-acetamido-3,6-dichloro-5-fluoropyridine-2-carboxylate Chemical compound COC(=O)C1=NC(Cl)=C(F)C(NC(C)=O)=C1Cl DKCGUEHEVORRHJ-UHFFFAOYSA-N 0.000 description 3
- 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 3
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 3
- 239000002798 polar solvent Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- CICGUYUXQJWNFS-UHFFFAOYSA-N propan-2-yl 4-amino-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylate Chemical compound COC1=C(Cl)C=CC(C=2C(=C(N)C=C(N=2)C(=O)OC(C)C)F)=C1F CICGUYUXQJWNFS-UHFFFAOYSA-N 0.000 description 3
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- HSNUXDIQZKIQRR-UHFFFAOYSA-N hydroxy-imino-bis(phenylmethoxy)-$l^{5}-phosphane Chemical compound C=1C=CC=CC=1COP(=O)(N)OCC1=CC=CC=C1 HSNUXDIQZKIQRR-UHFFFAOYSA-N 0.000 description 1
- RIGIWEGXTTUCIQ-UHFFFAOYSA-N hydroxy-imino-diphenyl-$l^{5}-phosphane Chemical compound C=1C=CC=CC=1P(=O)(N)C1=CC=CC=C1 RIGIWEGXTTUCIQ-UHFFFAOYSA-N 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 238000010952 in-situ formation Methods 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 239000012336 iodinating agent Substances 0.000 description 1
- 238000006192 iodination reaction Methods 0.000 description 1
- 159000000014 iron salts Chemical class 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229940049920 malate Drugs 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- LJDVXARAHMAOFP-UHFFFAOYSA-N methyl 4-acetamido-6-bromo-5-fluoropyridine-2-carboxylate Chemical compound COC(=O)C1=CC(NC(C)=O)=C(F)C(Br)=N1 LJDVXARAHMAOFP-UHFFFAOYSA-N 0.000 description 1
- CVYZJUXLXNJDEU-UHFFFAOYSA-N methyl 4-amino-6-bromo-3-chloro-5-fluoropyridine-2-carboxylate Chemical compound COC(=O)C1=NC(Br)=C(F)C(N)=C1Cl CVYZJUXLXNJDEU-UHFFFAOYSA-N 0.000 description 1
- GJRCHXIGVQXIPY-UHFFFAOYSA-N methyl 4-amino-6-bromo-5-fluoropyridine-2-carboxylate Chemical compound COC(=O)C1=CC(N)=C(F)C(Br)=N1 GJRCHXIGVQXIPY-UHFFFAOYSA-N 0.000 description 1
- ODRFMIJNQNBMMJ-UHFFFAOYSA-N methyl 6-(4-chloro-2-fluoro-3-methoxyphenyl)-4,5-difluoropyridine-2-carboxylate Chemical compound COC(=O)C1=CC(F)=C(F)C(C=2C(=C(OC)C(Cl)=CC=2)F)=N1 ODRFMIJNQNBMMJ-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- MEPIGJGXDFBYLW-UHFFFAOYSA-N n-(2,4,6-trimethyl-3-pyridin-2-ylphenyl)methanimine Chemical compound CC1=C(N=C)C(C)=CC(C)=C1C1=CC=CC=N1 MEPIGJGXDFBYLW-UHFFFAOYSA-N 0.000 description 1
- BAYDZXVPEQFLCZ-UHFFFAOYSA-N n-(2-trimethylsilylethoxy)methanamine Chemical compound CNOCC[Si](C)(C)C BAYDZXVPEQFLCZ-UHFFFAOYSA-N 0.000 description 1
- YNTOKMNHRPSGFU-UHFFFAOYSA-N n-Propyl carbamate Chemical compound CCCOC(N)=O YNTOKMNHRPSGFU-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- XBXCNNQPRYLIDE-UHFFFAOYSA-M n-tert-butylcarbamate Chemical compound CC(C)(C)NC([O-])=O XBXCNNQPRYLIDE-UHFFFAOYSA-M 0.000 description 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
- BMGNSKKZFQMGDH-FDGPNNRMSA-L nickel(2+);(z)-4-oxopent-2-en-2-olate Chemical compound [Ni+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O BMGNSKKZFQMGDH-FDGPNNRMSA-L 0.000 description 1
- ZBRJXVVKPBZPAN-UHFFFAOYSA-L nickel(2+);triphenylphosphane;dichloride Chemical compound [Cl-].[Cl-].[Ni+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 ZBRJXVVKPBZPAN-UHFFFAOYSA-L 0.000 description 1
- SFDJOSRHYKHMOK-UHFFFAOYSA-N nitramide Chemical compound N[N+]([O-])=O SFDJOSRHYKHMOK-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- XKLJHFLUAHKGGU-UHFFFAOYSA-N nitrous amide Chemical compound ON=N XKLJHFLUAHKGGU-UHFFFAOYSA-N 0.000 description 1
- 239000001702 nutmeg Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- 229940014662 pantothenate Drugs 0.000 description 1
- 235000019161 pantothenic acid Nutrition 0.000 description 1
- 239000011713 pantothenic acid Substances 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
- BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical compound NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 description 1
- AFDMODCXODAXLC-UHFFFAOYSA-N phenylmethanimine Chemical compound N=CC1=CC=CC=C1 AFDMODCXODAXLC-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- OCAAZRFBJBEVPS-UHFFFAOYSA-N prop-2-enyl carbamate Chemical compound NC(=O)OCC=C OCAAZRFBJBEVPS-UHFFFAOYSA-N 0.000 description 1
- YRGNDQQIUXCCAI-UHFFFAOYSA-N propan-2-yl 4,5,6-trifluoropyridine-2-carboxylate Chemical compound CC(C)OC(=O)C1=CC(F)=C(F)C(F)=N1 YRGNDQQIUXCCAI-UHFFFAOYSA-N 0.000 description 1
- PCHKPGRAPBRHIZ-UHFFFAOYSA-N propan-2-yl 4,5-difluoro-6-phenylpyridine-2-carboxylate Chemical compound CC(C)OC(=O)C1=CC(F)=C(F)C(C=2C=CC=CC=2)=N1 PCHKPGRAPBRHIZ-UHFFFAOYSA-N 0.000 description 1
- FHCDQJCSRTZQJW-UHFFFAOYSA-N propan-2-yl 4-acetamido-6-chloro-5-fluoropyridine-2-carboxylate Chemical compound CC(C)OC(=O)C1=CC(NC(C)=O)=C(F)C(Cl)=N1 FHCDQJCSRTZQJW-UHFFFAOYSA-N 0.000 description 1
- PIBVWUSLWKKFOU-UHFFFAOYSA-N propan-2-yl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylate Chemical compound COC1=C(Cl)C=CC(C=2C(=C(N)C(Cl)=C(C(=O)OC(C)C)N=2)F)=C1F PIBVWUSLWKKFOU-UHFFFAOYSA-N 0.000 description 1
- NAIYPGDHZPNRBP-UHFFFAOYSA-N pyridin-2-yl n-methylcarbamate Chemical compound CNC(=O)OC1=CC=CC=N1 NAIYPGDHZPNRBP-UHFFFAOYSA-N 0.000 description 1
- RWUGBYOALBYTGU-UHFFFAOYSA-N pyridin-4-ylmethyl carbamate Chemical compound NC(=O)OCC1=CC=NC=C1 RWUGBYOALBYTGU-UHFFFAOYSA-N 0.000 description 1
- PSAYJRPASWETSH-UHFFFAOYSA-N pyridine-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=CC=N1 PSAYJRPASWETSH-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- QVYNGEMFPFQXEZ-UHFFFAOYSA-N quinolin-8-ylcarbamic acid Chemical compound C1=CN=C2C(NC(=O)O)=CC=CC2=C1 QVYNGEMFPFQXEZ-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- RTKRAORYZUBVGQ-UHFFFAOYSA-N s-(2,4-dinitrophenyl)thiohydroxylamine Chemical compound NSC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O RTKRAORYZUBVGQ-UHFFFAOYSA-N 0.000 description 1
- LOVVSIULYJABJF-UHFFFAOYSA-N s-(2-nitrophenyl)thiohydroxylamine Chemical compound NSC1=CC=CC=C1[N+]([O-])=O LOVVSIULYJABJF-UHFFFAOYSA-N 0.000 description 1
- LOFZYSZWOLKUGE-UHFFFAOYSA-N s-benzyl carbamothioate Chemical compound NC(=O)SCC1=CC=CC=C1 LOFZYSZWOLKUGE-UHFFFAOYSA-N 0.000 description 1
- MAGSSGQAJNNDLU-UHFFFAOYSA-N s-phenylthiohydroxylamine Chemical compound NSC1=CC=CC=C1 MAGSSGQAJNNDLU-UHFFFAOYSA-N 0.000 description 1
- BPELEZSCHIEMAE-UHFFFAOYSA-N salicylaldehyde imine Chemical compound OC1=CC=CC=C1C=N BPELEZSCHIEMAE-UHFFFAOYSA-N 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000011272 standard treatment Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- NBNBICNWNFQDDD-UHFFFAOYSA-N sulfuryl dibromide Chemical compound BrS(Br)(=O)=O NBNBICNWNFQDDD-UHFFFAOYSA-N 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 229950002757 teoclate Drugs 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 150000004685 tetrahydrates Chemical class 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 150000004684 trihydrates Chemical class 0.000 description 1
- BZVJOYBTLHNRDW-UHFFFAOYSA-N triphenylmethanamine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(N)C1=CC=CC=C1 BZVJOYBTLHNRDW-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- LVLANIHJQRZTPY-UHFFFAOYSA-N vinyl carbamate Chemical compound NC(=O)OC=C LVLANIHJQRZTPY-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261675235P | 2012-07-24 | 2012-07-24 | |
| US61/675,235 | 2012-07-24 | ||
| PCT/US2013/051623 WO2014018502A1 (en) | 2012-07-24 | 2013-07-23 | Process for the preparation of 4-amino-5-fluoro-3-halo-6-(substituted)picolinates |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2015106019A RU2015106019A (ru) | 2016-09-10 |
| RU2632203C2 true RU2632203C2 (ru) | 2017-10-03 |
Family
ID=48901197
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2015106019A RU2632203C2 (ru) | 2012-07-24 | 2013-07-23 | Способ получения 4-амино-5-фтор-3-галоген-6-(замещенных)пиколинатов |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US8871943B2 (enExample) |
| EP (1) | EP2877453B1 (enExample) |
| JP (1) | JP6046817B2 (enExample) |
| KR (1) | KR101946681B1 (enExample) |
| CN (1) | CN104640844B (enExample) |
| AR (1) | AR091856A1 (enExample) |
| AU (1) | AU2013293200B2 (enExample) |
| BR (1) | BR112015001615B8 (enExample) |
| CA (1) | CA2879530C (enExample) |
| CO (1) | CO7200265A2 (enExample) |
| IL (1) | IL236816A (enExample) |
| IN (1) | IN2015DN00821A (enExample) |
| MX (1) | MX351886B (enExample) |
| NZ (1) | NZ704103A (enExample) |
| PL (1) | PL2877453T3 (enExample) |
| RU (1) | RU2632203C2 (enExample) |
| TW (1) | TWI577663B (enExample) |
| UY (1) | UY34946A (enExample) |
| WO (1) | WO2014018502A1 (enExample) |
| ZA (1) | ZA201500701B (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR092355A1 (es) * | 2012-07-24 | 2015-04-15 | Dow Agrosciences Llc | Fluoruros de fluoropicolinoilo y procesos para su preparacion |
| US8764316B1 (en) | 2013-05-23 | 2014-07-01 | Corning Cable Systems Llc | Fiber optic connector with vented ferrule holder |
| TW201609651A (zh) | 2013-11-12 | 2016-03-16 | 陶氏農業科學公司 | 用於氟化化合物之過程（一） |
| BR102014028164A2 (pt) * | 2013-11-12 | 2015-09-08 | Dow Agrosciences Llc | processo para fluoração de compostos |
| TW201609652A (zh) | 2013-11-12 | 2016-03-16 | 陶氏農業科學公司 | 用於氟化化合物之過程（三） |
| TWI726900B (zh) | 2015-08-04 | 2021-05-11 | 美商陶氏農業科學公司 | 用於氟化化合物之過程 |
| CA3012167A1 (en) * | 2016-01-22 | 2017-07-27 | Dow Agrosciences Llc | Process for the preparation of 4-alkoxy-3-acetoxypicolinic acids |
| 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 |
| EP3555049A4 (en) * | 2016-12-13 | 2020-04-29 | Dow AgroSciences LLC | Method of preparing benzy 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl)picolinate |
| EP3853205A1 (en) * | 2018-09-19 | 2021-07-28 | Corteva Agriscience LLC | Preparation of halogen analogs of picloram |
| BR112022018508A2 (pt) * | 2020-03-18 | 2022-10-25 | Corteva Agriscience Llc | Síntese melhorada de 4-amino-6-(heterocíclico)picolinatos |
| CN114702440B (zh) * | 2022-04-26 | 2024-06-18 | 永农生物科学有限公司 | 一种氨氯吡啶酸的制备方法及制备的氨氯吡啶酸 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US4847442A (en) * | 1988-07-18 | 1989-07-11 | Allied-Signal Inc. | Process for the preparation of difluorobenzenes |
| RU2332404C2 (ru) * | 2003-04-02 | 2008-08-27 | Дау Агросайенсиз Ллс | 6-алкил или алкенил-4-аминопиколинаты и их применение в качестве гербицидов |
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| JP2520254B2 (ja) * | 1987-04-28 | 1996-07-31 | イハラケミカル工業株式会社 | ３，４，５−トリフルオロ安息香酸誘導体およびその製造方法 |
| US6297197B1 (en) | 2000-01-14 | 2001-10-02 | Dow Agrosciences Llc | 4-aminopicolinates and their use as herbicides |
| 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 |
| AU2003238390A1 (en) * | 2002-06-04 | 2003-12-19 | Clariant Gmbh | Method for producing a compound containing fluorine via fluorine-halogen exchange by special polyamino phosphazene catalysts |
| AR059010A1 (es) | 2006-01-13 | 2008-03-05 | Dow Agrosciences Llc | 6-( aril polisustituido )-4- aminopicolinatos y su uso como herbicidas |
| 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 |
| TWI537252B (zh) | 2011-01-25 | 2016-06-11 | 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（一） |
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2013
- 2013-07-22 AR ARP130102597A patent/AR091856A1/es active IP Right Grant
- 2013-07-23 EP EP13742581.5A patent/EP2877453B1/en active Active
- 2013-07-23 WO PCT/US2013/051623 patent/WO2014018502A1/en not_active Ceased
- 2013-07-23 RU RU2015106019A patent/RU2632203C2/ru active
- 2013-07-23 PL PL13742581T patent/PL2877453T3/pl unknown
- 2013-07-23 NZ NZ704103A patent/NZ704103A/en unknown
- 2013-07-23 CN CN201380048518.6A patent/CN104640844B/zh active Active
- 2013-07-23 CA CA2879530A patent/CA2879530C/en active Active
- 2013-07-23 TW TW102126266A patent/TWI577663B/zh active
- 2013-07-23 US US13/949,060 patent/US8871943B2/en active Active
- 2013-07-23 MX MX2015001141A patent/MX351886B/es active IP Right Grant
- 2013-07-23 BR BR112015001615A patent/BR112015001615B8/pt active IP Right Grant
- 2013-07-23 UY UY0001034946A patent/UY34946A/es active IP Right Grant
- 2013-07-23 KR KR1020157004099A patent/KR101946681B1/ko active Active
- 2013-07-23 AU AU2013293200A patent/AU2013293200B2/en active Active
- 2013-07-23 IN IN821DEN2015 patent/IN2015DN00821A/en unknown
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2015
- 2015-01-20 IL IL236816A patent/IL236816A/en active IP Right Grant
- 2015-01-30 ZA ZA2015/00701A patent/ZA201500701B/en unknown
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| US4847442A (en) * | 1988-07-18 | 1989-07-11 | Allied-Signal Inc. | Process for the preparation of difluorobenzenes |
| RU2332404C2 (ru) * | 2003-04-02 | 2008-08-27 | Дау Агросайенсиз Ллс | 6-алкил или алкенил-4-аминопиколинаты и их применение в качестве гербицидов |
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| Jørn B. Christensen, et al. "TFFH as an Excellent Reagent for Acylation of Alcohols, Thiols and Dithiocarbamates". SYNTHESIS, vol.15, 2004, p.2485-2492, DOI: 10.1055/s-2004-831250. * |
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| AR091856A1 (es) | 2015-03-04 |
| BR112015001615B1 (pt) | 2019-10-22 |
| PL2877453T3 (pl) | 2017-08-31 |
| KR101946681B1 (ko) | 2019-02-11 |
| MX351886B (es) | 2017-11-01 |
| US20140031556A1 (en) | 2014-01-30 |
| EP2877453B1 (en) | 2016-07-06 |
| CO7200265A2 (es) | 2015-02-27 |
| CN104640844A (zh) | 2015-05-20 |
| CA2879530A1 (en) | 2014-01-30 |
| UY34946A (es) | 2014-02-28 |
| IL236816A (en) | 2016-11-30 |
| NZ704103A (en) | 2016-08-26 |
| BR112015001615A2 (pt) | 2017-07-04 |
| AU2013293200A1 (en) | 2015-02-19 |
| WO2014018502A1 (en) | 2014-01-30 |
| IN2015DN00821A (enExample) | 2015-06-12 |
| BR112015001615B8 (pt) | 2022-08-23 |
| EP2877453A1 (en) | 2015-06-03 |
| JP2015530367A (ja) | 2015-10-15 |
| US8871943B2 (en) | 2014-10-28 |
| JP6046817B2 (ja) | 2016-12-21 |
| TWI577663B (zh) | 2017-04-11 |
| RU2015106019A (ru) | 2016-09-10 |
| CA2879530C (en) | 2019-06-18 |
| CN104640844B (zh) | 2016-11-09 |
| HK1210613A1 (en) | 2016-04-29 |
| TW201406726A (zh) | 2014-02-16 |
| KR20150036673A (ko) | 2015-04-07 |
| MX2015001141A (es) | 2015-09-08 |
| AU2013293200B2 (en) | 2016-11-17 |
| ZA201500701B (en) | 2016-10-26 |
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