JP2019516708A5 - - Google Patents
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- Publication number
- JP2019516708A5 JP2019516708A5 JP2018560490A JP2018560490A JP2019516708A5 JP 2019516708 A5 JP2019516708 A5 JP 2019516708A5 JP 2018560490 A JP2018560490 A JP 2018560490A JP 2018560490 A JP2018560490 A JP 2018560490A JP 2019516708 A5 JP2019516708 A5 JP 2019516708A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- catalyst
- halogen
- alkoxy
- aryl
- 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.)
- Granted
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- 238000000034 method Methods 0.000 claims 18
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 claims 12
- 125000000217 alkyl group Chemical group 0.000 claims 9
- 239000003054 catalyst Substances 0.000 claims 9
- 229910052736 halogen Chemical group 0.000 claims 8
- 150000002367 halogens Chemical group 0.000 claims 8
- 238000006069 Suzuki reaction reaction Methods 0.000 claims 7
- 125000003545 alkoxy group Chemical group 0.000 claims 7
- 150000003927 aminopyridines Chemical class 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 3
- 239000012035 limiting reagent Substances 0.000 claims 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 230000008878 coupling Effects 0.000 claims 2
- 238000010168 coupling process Methods 0.000 claims 2
- 238000005859 coupling reaction Methods 0.000 claims 2
- 150000002431 hydrogen Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 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 1
- 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 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 239000013058 crude material Substances 0.000 claims 1
- 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 1
- 239000000203 mixture Substances 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 claims 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical group [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2022118930A JP2022141912A (ja) | 2016-05-19 | 2022-07-26 | 直接的な鈴木カップリングによる６－アリール－４－アミノピコリネートおよび２－アリール－６－アミノピリミジン－４－カルボキシレートの合成 |
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662338562P | 2016-05-19 | 2016-05-19 | |
| US62/338,562 | 2016-05-19 | ||
| US201662416811P | 2016-11-03 | 2016-11-03 | |
| US62/416,811 | 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 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022118930A Division JP2022141912A (ja) | 2016-05-19 | 2022-07-26 | 直接的な鈴木カップリングによる６－アリール－４－アミノピコリネートおよび２－アリール－６－アミノピリミジン－４－カルボキシレートの合成 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019516708A JP2019516708A (ja) | 2019-06-20 |
| JP2019516708A5 true JP2019516708A5 (cg-RX-API-DMAC7.html) | 2020-07-02 |
| JP7113762B2 JP7113762B2 (ja) | 2022-08-05 |
Family
ID=60326419
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018560490A Active JP7113762B2 (ja) | 2016-05-19 | 2017-05-19 | 直接的な鈴木カップリングによる６－アリール－４－アミノピコリネートおよび２－アリール－６－アミノピリミジン－４－カルボキシレートの合成 |
| JP2022118930A Ceased JP2022141912A (ja) | 2016-05-19 | 2022-07-26 | 直接的な鈴木カップリングによる６－アリール－４－アミノピコリネートおよび２－アリール－６－アミノピリミジン－４－カルボキシレートの合成 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022118930A Ceased JP2022141912A (ja) | 2016-05-19 | 2022-07-26 | 直接的な鈴木カップリングによる６－アリール－４－アミノピコリネートおよび２－アリール－６－アミノピリミジン－４－カルボキシレートの合成 |
Country Status (12)
| Country | Link |
|---|---|
| US (3) | US10087164B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP3458442B1 (cg-RX-API-DMAC7.html) |
| JP (2) | JP7113762B2 (cg-RX-API-DMAC7.html) |
| KR (1) | KR20190007048A (cg-RX-API-DMAC7.html) |
| CN (1) | CN109415319A (cg-RX-API-DMAC7.html) |
| AU (2) | AU2017268424B2 (cg-RX-API-DMAC7.html) |
| BR (1) | BR112018073348B8 (cg-RX-API-DMAC7.html) |
| CA (1) | CA3023935A1 (cg-RX-API-DMAC7.html) |
| IL (1) | IL263075A (cg-RX-API-DMAC7.html) |
| MX (1) | MX2018014174A (cg-RX-API-DMAC7.html) |
| RU (1) | RU2018144344A (cg-RX-API-DMAC7.html) |
| WO (1) | WO2017201377A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US11401242B2 (en) * | 2018-09-19 | 2022-08-02 | Corteva Agriscience Llc | Preparation of halogen analogs of picloram |
| 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 |
| CN115298167A (zh) | 2020-03-18 | 2022-11-04 | 科迪华农业科技有限责任公司 | 6-芳基-4-氨基吡啶甲酸酯的改进合成 |
| 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 |
| WO2021231196A1 (en) * | 2020-05-11 | 2021-11-18 | 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 |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| MY149916A (en) * | 2006-01-13 | 2013-10-31 | Dow Agrosciences Llc | 2-(poly-substituted aryl)-6-amino-5-halo-4-pyrimidinecarboxylic acids and their use as herbicides |
| EP2176239B1 (en) * | 2007-08-13 | 2012-12-19 | Dow AgroSciences LLC | 2-(2-fluoro-substituted phenyl)-6-amino-5-chloro-4-pyrimidinecarboxylates and their use as herbicides |
| DE602008005319D1 (de) * | 2007-08-30 | 2011-04-14 | Dow Agrosciences Llc | 2-(substituierte phenyl)-6-amino-5-alkoxy-, thioalkoxy- und aminoalkyl-4-pyrimidincarboxylate und ihre verwendung als herbizide |
| DK2327695T3 (da) | 2007-10-02 | 2012-10-29 | Dow Agrosciences Llc | Substituerede 4-amino-picolinsyrer og deres anvendelse som herbicider |
| 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 |
| 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） |
| US8658568B2 (en) * | 2011-01-25 | 2014-02-25 | Dow Agrosciences, Llc. | 6-amino-2-substituted-5-vinylsilylpyrimidine-4-carboxylic acids and esters and 4-amino-6-substituted-3-vinylsilylpyridine-2-carboxylic acids and esters as herbicides |
| 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） |
| HUE028580T2 (en) * | 2011-07-27 | 2016-12-28 | Bayer Ip Gmbh | Substituted Picolinic Acids and Pyrimidine Carboxylic Acids, Process for their Preparation and Use as Herbicides and Plant Growth Regulators |
| CN104080791B (zh) * | 2011-12-30 | 2016-12-07 | 陶氏益农公司 | 分离和使用(4-氯-2-氟-3-取代的-苯基)硼酸酯的方法 |
| BR112014015962B8 (pt) * | 2011-12-30 | 2022-10-11 | Dow Agrosciences Llc | Métodos para produzir 4-amino-3-cloro-6-(4-cloro-2-flúor-3-metóxi-fenil)piridina-2-carboxilato de metila |
| 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 |
| EP2970186B1 (en) | 2013-03-15 | 2020-06-10 | Dow AgroSciences LLC | 4-amino-6-(heterocyclic)picolinates and 6-amino-2-(heterocyclic) pyrimidine-4-carboxylates and their use as herbicides |
| JP2016514138A (ja) * | 2013-03-15 | 2016-05-19 | ダウ アグロサイエンシィズ エルエルシー | 除草剤としての新規な４−アミノピリジンカルボキシレートおよび６−アミノピリミジンカルボキシレート |
| 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 |
| MX2015012947A (es) * | 2013-03-15 | 2016-06-02 | Dow Agrosciences Llc | 4-amino-6-(heterociclico) picolinatos y 6-amino-2-(heterociclico) pirimidina-4-carboxilatos 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 |
| 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 |
-
2017
- 2017-05-19 EP EP17800225.9A patent/EP3458442B1/en active Active
- 2017-05-19 WO PCT/US2017/033489 patent/WO2017201377A1/en not_active Ceased
- 2017-05-19 BR BR112018073348A patent/BR112018073348B8/pt active IP Right Grant
- 2017-05-19 RU RU2018144344A patent/RU2018144344A/ru unknown
- 2017-05-19 MX MX2018014174A patent/MX2018014174A/es unknown
- 2017-05-19 KR KR1020187036364A patent/KR20190007048A/ko not_active Abandoned
- 2017-05-19 JP JP2018560490A patent/JP7113762B2/ja active Active
- 2017-05-19 CN CN201780042463.6A patent/CN109415319A/zh active Pending
- 2017-05-19 AU AU2017268424A patent/AU2017268424B2/en not_active Ceased
- 2017-05-19 US US15/599,716 patent/US10087164B2/en active Active
- 2017-05-19 CA CA3023935A patent/CA3023935A1/en active Pending
-
2018
- 2018-07-26 US US16/045,896 patent/US10544121B2/en active Active
- 2018-07-26 US US16/045,901 patent/US10570114B2/en active Active
- 2018-11-18 IL IL263075A patent/IL263075A/en unknown
-
2021
- 2021-05-20 AU AU2021203233A patent/AU2021203233A1/en not_active Abandoned
-
2022
- 2022-07-26 JP JP2022118930A patent/JP2022141912A/ja not_active Ceased
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