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
- Authority
- CA
- Canada
- Prior art keywords
- catalyst
- alkyl
- aryl
- chloro
- suzuki coupling
- 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.)
- Pending
Links
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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA3023935A1 true CA3023935A1 (en) | 2017-11-23 |
Family
ID=60326419
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA3023935A Pending CA3023935A1 (en) | 2016-05-19 | 2017-05-19 | Synthesis of 6-aryl-4-aminopicolinates and 2-aryl-6-aminopyrimidine-4-carboxylates by direct suzuki coupling |
Country Status (12)
| Country | Link |
|---|---|
| US (3) | US10087164B2 (https=) |
| EP (1) | EP3458442B1 (https=) |
| JP (2) | JP7113762B2 (https=) |
| KR (1) | KR20190007048A (https=) |
| CN (1) | CN109415319A (https=) |
| AU (2) | AU2017268424B2 (https=) |
| BR (1) | BR112018073348B8 (https=) |
| CA (1) | CA3023935A1 (https=) |
| IL (1) | IL263075A (https=) |
| MX (1) | MX2018014174A (https=) |
| RU (1) | RU2018144344A (https=) |
| WO (1) | WO2017201377A1 (https=) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10087164B2 (en) * | 2016-05-19 | 2018-10-02 | Dow Agrosciences Llc | Synthesis of 6-aryl-4-aminopicolinates and 2-aryl-6-aminopyrimidine-4-carboxylates by direct Suzuki coupling |
| EP3853205A1 (en) * | 2018-09-19 | 2021-07-28 | 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 |
| WO2021188639A1 (en) | 2020-03-18 | 2021-09-23 | 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 |
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 |
| CA2626018C (en) * | 2006-01-13 | 2014-05-06 | Dow Agrosciences Llc | 2-(poly-substituted aryl)-6-amino-5-halo-4-pyrimidinecarboxylic acids and their use as herbicides |
| ES2400405T3 (es) * | 2007-08-13 | 2013-04-09 | Dow Agrosciences Llc | 2-(Fenil 2-fluoro-substituido)-6-amino-5-cloro-4-pirimidinacarboxilatos y su uso como herbicidas |
| MY150491A (en) * | 2007-08-30 | 2014-01-30 | Dow Agrosciences Llc | 2-(substituted phenyl)-6-amino-5-alkoxy, thioalkoxy and aminoalkyl 4- pyrimidinecarboxylates and their use as herbicides |
| CA2699598C (en) * | 2007-10-02 | 2013-05-21 | Dow Agrosciences Llc | 2-substituted-6-amino-5-alkyl, alkenyl or alkynyl-4-pyrimidinecarboxylic acids and 6-substituted-4-amino-3-alkyl, alkenyl or alkynyl picolinic acids and their use as herbicides |
| EP2279178B1 (en) * | 2008-04-18 | 2015-05-20 | Dow AgroSciences LLC | 2-(substituted phenyl)-6-hydroxy- or alkoxy-5-substituted-4-pyrimidinecarboxylates and their use as herbicides |
| 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 |
| KR101554404B1 (ko) * | 2011-01-25 | 2015-09-18 | 다우 아그로사이언시즈 엘엘씨 | 제초제로서의 6-아미노-2-치환된-5-비닐실릴피리미딘-4-카르복실산 및 에스테르 및 4-아미노-6-치환된-3-비닐실릴피리딘-2-카르복실산 및 에스테르 |
| 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 |
| TWI547482B (zh) | 2011-01-25 | 2016-09-01 | 陶氏農業科學公司 | 增加可回收之3-氯-4,5,6-三氟-2-氰吡啶之量的改良方法 |
| 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） |
| ES2561887T3 (es) * | 2011-07-27 | 2016-03-01 | Bayer Intellectual Property Gmbh | Ácidos picolínicos y piridimin-4-carboxílicos sustituidos, procedimiento para su preparación y su uso como herbicidas y reguladores del crecimiento de plantas |
| 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 |
| RU2616621C2 (ru) * | 2011-12-30 | 2017-04-18 | ДАУ АГРОСАЙЕНСИЗ ЭлЭлСи | Способы получения метил 4-амино-3-хлор-6-(4-хлор-2-фтор-3-метоксифенил)пиридин-2-карбоксилата |
| 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 |
| ES2712103T3 (es) * | 2013-03-15 | 2019-05-09 | Dow Agrosciences Llc | Nuevos carboxilatos de 4-aminopiridina y 6-aminopirimidina como herbicidas |
| 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 |
| 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 |
| 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 |
| CN110583663A (zh) | 2013-03-15 | 2019-12-20 | 美国陶氏益农公司 | 式(i)化合物及其作为除草剂的用途 |
| US10087164B2 (en) * | 2016-05-19 | 2018-10-02 | Dow Agrosciences Llc | Synthesis of 6-aryl-4-aminopicolinates and 2-aryl-6-aminopyrimidine-4-carboxylates by direct Suzuki coupling |
-
2017
- 2017-05-19 US US15/599,716 patent/US10087164B2/en active Active
- 2017-05-19 CN CN201780042463.6A patent/CN109415319A/zh active Pending
- 2017-05-19 JP JP2018560490A patent/JP7113762B2/ja active Active
- 2017-05-19 WO PCT/US2017/033489 patent/WO2017201377A1/en not_active Ceased
- 2017-05-19 KR KR1020187036364A patent/KR20190007048A/ko not_active Abandoned
- 2017-05-19 AU AU2017268424A patent/AU2017268424B2/en not_active Ceased
- 2017-05-19 CA CA3023935A patent/CA3023935A1/en active Pending
- 2017-05-19 RU RU2018144344A patent/RU2018144344A/ru unknown
- 2017-05-19 EP EP17800225.9A patent/EP3458442B1/en active Active
- 2017-05-19 BR BR112018073348A patent/BR112018073348B8/pt active IP Right Grant
- 2017-05-19 MX MX2018014174A patent/MX2018014174A/es unknown
-
2018
- 2018-07-26 US US16/045,901 patent/US10570114B2/en active Active
- 2018-07-26 US US16/045,896 patent/US10544121B2/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
Also Published As
| Publication number | Publication date |
|---|---|
| EP3458442B1 (en) | 2022-12-28 |
| US20170334878A1 (en) | 2017-11-23 |
| MX2018014174A (es) | 2019-03-14 |
| US20180334444A1 (en) | 2018-11-22 |
| NZ747932A (en) | 2022-03-25 |
| IL263075A (en) | 2018-12-31 |
| AU2017268424A1 (en) | 2018-11-22 |
| JP7113762B2 (ja) | 2022-08-05 |
| US10544121B2 (en) | 2020-01-28 |
| KR20190007048A (ko) | 2019-01-21 |
| EP3458442A4 (en) | 2020-04-22 |
| JP2022141912A (ja) | 2022-09-29 |
| US10087164B2 (en) | 2018-10-02 |
| JP2019516708A (ja) | 2019-06-20 |
| BR112018073348B1 (pt) | 2023-01-24 |
| RU2018144344A (ru) | 2020-06-19 |
| EP3458442A1 (en) | 2019-03-27 |
| CN109415319A (zh) | 2019-03-01 |
| BR112018073348A2 (pt) | 2019-03-06 |
| RU2018144344A3 (https=) | 2021-02-18 |
| WO2017201377A1 (en) | 2017-11-23 |
| BR112018073348B8 (pt) | 2023-05-16 |
| AU2021203233A1 (en) | 2021-06-10 |
| US20180334445A1 (en) | 2018-11-22 |
| US10570114B2 (en) | 2020-02-25 |
| AU2017268424B2 (en) | 2021-07-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20220518 |