KR20190007048A - 직접 스즈키 커플링에 의한 6-아릴-4-아미노피콜리네이트 및 2-아릴-6-아미노피리미딘-4-카르복실레이트의 합성 - Google Patents
직접 스즈키 커플링에 의한 6-아릴-4-아미노피콜리네이트 및 2-아릴-6-아미노피리미딘-4-카르복실레이트의 합성 Download PDFInfo
- Publication number
- KR20190007048A KR20190007048A KR1020187036364A KR20187036364A KR20190007048A KR 20190007048 A KR20190007048 A KR 20190007048A KR 1020187036364 A KR1020187036364 A KR 1020187036364A KR 20187036364 A KR20187036364 A KR 20187036364A KR 20190007048 A KR20190007048 A KR 20190007048A
- Authority
- KR
- South Korea
- Prior art keywords
- catalyst
- alkyl
- aryl
- suzuki coupling
- alkoxy
- 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.)
- Abandoned
Links
- 0 *C(c1nc(Cl)c(*)c(*)c1*)=O Chemical compound *C(c1nc(Cl)c(*)c(*)c1*)=O 0.000 description 4
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
-
- B01J35/0046—
-
- 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 | |
| US62/338,562 | 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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20190007048A true KR20190007048A (ko) | 2019-01-21 |
Family
ID=60326419
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020187036364A Abandoned KR20190007048A (ko) | 2016-05-19 | 2017-05-19 | 직접 스즈키 커플링에 의한 6-아릴-4-아미노피콜리네이트 및 2-아릴-6-아미노피리미딘-4-카르복실레이트의 합성 |
Country Status (12)
| Country | Link |
|---|---|
| US (3) | US10087164B2 (enExample) |
| EP (1) | EP3458442B1 (enExample) |
| JP (2) | JP7113762B2 (enExample) |
| KR (1) | KR20190007048A (enExample) |
| CN (1) | CN109415319A (enExample) |
| AU (2) | AU2017268424B2 (enExample) |
| BR (1) | BR112018073348B8 (enExample) |
| CA (1) | CA3023935A1 (enExample) |
| IL (1) | IL263075A (enExample) |
| MX (1) | MX2018014174A (enExample) |
| RU (1) | RU2018144344A (enExample) |
| WO (1) | WO2017201377A1 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
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 |
| 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 |
-
2017
- 2017-05-19 BR BR112018073348A patent/BR112018073348B8/pt active IP Right Grant
- 2017-05-19 RU RU2018144344A patent/RU2018144344A/ru unknown
- 2017-05-19 WO PCT/US2017/033489 patent/WO2017201377A1/en not_active Ceased
- 2017-05-19 CA CA3023935A patent/CA3023935A1/en active Pending
- 2017-05-19 MX MX2018014174A patent/MX2018014174A/es unknown
- 2017-05-19 JP JP2018560490A patent/JP7113762B2/ja active Active
- 2017-05-19 EP EP17800225.9A patent/EP3458442B1/en active Active
- 2017-05-19 KR KR1020187036364A patent/KR20190007048A/ko not_active Abandoned
- 2017-05-19 CN CN201780042463.6A patent/CN109415319A/zh active Pending
- 2017-05-19 US US15/599,716 patent/US10087164B2/en active Active
- 2017-05-19 AU AU2017268424A patent/AU2017268424B2/en not_active Ceased
-
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
Also Published As
| Publication number | Publication date |
|---|---|
| EP3458442A1 (en) | 2019-03-27 |
| 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 |
| JP7113762B2 (ja) | 2022-08-05 |
| US20180334445A1 (en) | 2018-11-22 |
| RU2018144344A (ru) | 2020-06-19 |
| JP2019516708A (ja) | 2019-06-20 |
| WO2017201377A1 (en) | 2017-11-23 |
| CA3023935A1 (en) | 2017-11-23 |
| US10544121B2 (en) | 2020-01-28 |
| BR112018073348A2 (pt) | 2019-03-06 |
| CN109415319A (zh) | 2019-03-01 |
| 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 |
| EP3458442A4 (en) | 2020-04-22 |
| AU2017268424B2 (en) | 2021-07-15 |
| US20170334878A1 (en) | 2017-11-23 |
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