JP2015530367A5 - - Google Patents
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- Publication number
- JP2015530367A5 JP2015530367A5 JP2015524380A JP2015524380A JP2015530367A5 JP 2015530367 A5 JP2015530367 A5 JP 2015530367A5 JP 2015524380 A JP2015524380 A JP 2015524380A JP 2015524380 A JP2015524380 A JP 2015524380A JP 2015530367 A5 JP2015530367 A5 JP 2015530367A5
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- JP
- Japan
- Prior art keywords
- formula
- compound
- forming
- alkyl
- following
- 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.)
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- 150000001875 compounds Chemical class 0.000 claims 75
- 238000000034 method Methods 0.000 claims 21
- 230000009466 transformation Effects 0.000 claims 17
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 12
- 229910052736 halogen Inorganic materials 0.000 claims 11
- 150000002367 halogens Chemical class 0.000 claims 11
- 239000003054 catalyst Substances 0.000 claims 7
- 229910052801 chlorine Inorganic materials 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- 229910021529 ammonia Inorganic materials 0.000 claims 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 5
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims 5
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims 5
- 229910052794 bromium Inorganic materials 0.000 claims 5
- 238000006243 chemical reaction Methods 0.000 claims 5
- 229910052802 copper Inorganic materials 0.000 claims 5
- 239000010949 copper Substances 0.000 claims 5
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 5
- -1 fluoride ions Chemical class 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 229910052740 iodine Inorganic materials 0.000 claims 5
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 229910052723 transition metal Inorganic materials 0.000 claims 5
- 150000003624 transition metals Chemical class 0.000 claims 5
- 239000002253 acid Substances 0.000 claims 4
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 3
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- 238000005576 amination reaction Methods 0.000 claims 3
- 150000001412 amines Chemical class 0.000 claims 3
- 150000003983 crown ethers Chemical class 0.000 claims 3
- 230000002140 halogenating effect Effects 0.000 claims 3
- 229910001512 metal fluoride Inorganic materials 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 230000015572 biosynthetic process Effects 0.000 claims 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 claims 2
- 150000001805 chlorine compounds Chemical class 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 238000003682 fluorination reaction Methods 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 2
- 235000003270 potassium fluoride Nutrition 0.000 claims 2
- 239000011698 potassium fluoride Substances 0.000 claims 2
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical group [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 claims 2
- 150000003990 18-crown-6 derivatives Chemical group 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 238000010511 deprotection reaction Methods 0.000 claims 1
- 238000000605 extraction Methods 0.000 claims 1
- 230000036571 hydration Effects 0.000 claims 1
- 238000006703 hydration reaction Methods 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000007935 neutral effect Effects 0.000 claims 1
- 230000003472 neutralizing effect Effects 0.000 claims 1
- 229920000570 polyether Polymers 0.000 claims 1
- 238000001556 precipitation Methods 0.000 claims 1
- 235000013024 sodium fluoride Nutrition 0.000 claims 1
- 239000011775 sodium fluoride Substances 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims 1
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 (3)
| Publication Number | Publication Date |
|---|---|
| JP2015530367A JP2015530367A (ja) | 2015-10-15 |
| JP2015530367A5 true JP2015530367A5 (cg-RX-API-DMAC7.html) | 2016-09-08 |
| JP6046817B2 JP6046817B2 (ja) | 2016-12-21 |
Family
ID=48901197
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015524380A Active JP6046817B2 (ja) | 2012-07-24 | 2013-07-23 | ４−アミノ−５−フルオロ−３−ハロ−６−（置換）ピコリナートの調製プロセス |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US8871943B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP2877453B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP6046817B2 (cg-RX-API-DMAC7.html) |
| KR (1) | KR101946681B1 (cg-RX-API-DMAC7.html) |
| CN (1) | CN104640844B (cg-RX-API-DMAC7.html) |
| AR (1) | AR091856A1 (cg-RX-API-DMAC7.html) |
| AU (1) | AU2013293200B2 (cg-RX-API-DMAC7.html) |
| BR (1) | BR112015001615B8 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2879530C (cg-RX-API-DMAC7.html) |
| CO (1) | CO7200265A2 (cg-RX-API-DMAC7.html) |
| IL (1) | IL236816A (cg-RX-API-DMAC7.html) |
| IN (1) | IN2015DN00821A (cg-RX-API-DMAC7.html) |
| MX (1) | MX351886B (cg-RX-API-DMAC7.html) |
| NZ (1) | NZ704103A (cg-RX-API-DMAC7.html) |
| PL (1) | PL2877453T3 (cg-RX-API-DMAC7.html) |
| RU (1) | RU2632203C2 (cg-RX-API-DMAC7.html) |
| TW (1) | TWI577663B (cg-RX-API-DMAC7.html) |
| UY (1) | UY34946A (cg-RX-API-DMAC7.html) |
| WO (1) | WO2014018502A1 (cg-RX-API-DMAC7.html) |
| ZA (1) | ZA201500701B (cg-RX-API-DMAC7.html) |
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 |
| BR102014028164A2 (pt) * | 2013-11-12 | 2015-09-08 | Dow Agrosciences Llc | processo para fluoração de compostos |
| 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） |
| 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 |
| US10259789B2 (en) * | 2016-01-22 | 2019-04-16 | Dow Agrosciences Llc | Process for the preparation of 4-alkoxy-3-acetoxypicolinic acids |
| EP3458442B1 (en) | 2016-05-19 | 2022-12-28 | Corteva Agriscience LLC | Synthesis of 6-aryl-4-aminopicolinates and 2-aryl-6-aminopyrimidine-4-carboxylates by direct suzuki coupling |
| WO2018111639A1 (en) * | 2016-12-13 | 2018-06-21 | Dow Agrosciences Llc | Method of preparing benzy 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl)picolinate |
| US11401242B2 (en) | 2018-09-19 | 2022-08-02 | Corteva Agriscience Llc | Preparation of halogen analogs of picloram |
| CN115279737A (zh) * | 2020-03-18 | 2022-11-01 | 科迪华农业科技有限责任公司 | 4-氨基-6-(杂环)吡啶甲酸酯的改进合成 |
| 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 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US4847442A (en) * | 1988-07-18 | 1989-07-11 | Allied-Signal Inc. | Process for the preparation of difluorobenzenes |
| 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 |
| WO2003101926A1 (de) | 2002-06-04 | 2003-12-11 | Clariant Gmbh | Verfahren zur herstellung von fluor enthaltenden verbindungen über fluor-halogenaustausch durch spezielle polyaminophosphazen-katalysatoren |
| UA82358C2 (uk) | 2003-04-02 | 2008-04-10 | Дау Агросайенсиз Ллс | 6-алкіл або алкеніл-4-амінопіколінати гербіцидна композиція, спосіб боротьби з небажаною рослинністю |
| RU2428416C2 (ru) * | 2006-01-13 | 2011-09-10 | Дау Агросайенсиз Ллс | 6-(полизамещенный арил)-4-аминопиколинаты и их применение в качестве гербицидов |
| 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） |
| 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 |
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2013
- 2013-07-22 AR ARP130102597A patent/AR091856A1/es active IP Right Grant
- 2013-07-23 TW TW102126266A patent/TWI577663B/zh active
- 2013-07-23 JP JP2015524380A patent/JP6046817B2/ja active Active
- 2013-07-23 EP EP13742581.5A patent/EP2877453B1/en active Active
- 2013-07-23 MX MX2015001141A patent/MX351886B/es active IP Right Grant
- 2013-07-23 PL PL13742581T patent/PL2877453T3/pl unknown
- 2013-07-23 UY UY0001034946A patent/UY34946A/es active IP Right Grant
- 2013-07-23 CN CN201380048518.6A patent/CN104640844B/zh active Active
- 2013-07-23 KR KR1020157004099A patent/KR101946681B1/ko active Active
- 2013-07-23 IN IN821DEN2015 patent/IN2015DN00821A/en unknown
- 2013-07-23 WO PCT/US2013/051623 patent/WO2014018502A1/en not_active Ceased
- 2013-07-23 US US13/949,060 patent/US8871943B2/en active Active
- 2013-07-23 NZ NZ704103A patent/NZ704103A/en unknown
- 2013-07-23 AU AU2013293200A patent/AU2013293200B2/en active Active
- 2013-07-23 RU RU2015106019A patent/RU2632203C2/ru active
- 2013-07-23 CA CA2879530A patent/CA2879530C/en active Active
- 2013-07-23 BR BR112015001615A patent/BR112015001615B8/pt active IP Right Grant
-
2015
- 2015-01-20 IL IL236816A patent/IL236816A/en active IP Right Grant
- 2015-01-30 ZA ZA2015/00701A patent/ZA201500701B/en unknown
- 2015-02-06 CO CO15024012A patent/CO7200265A2/es unknown