CN109415319A - 通过直接苏楚基偶联合成芳基羧酸酯 - Google Patents

通过直接苏楚基偶联合成芳基羧酸酯 Download PDF

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Publication number
CN109415319A
CN109415319A CN201780042463.6A CN201780042463A CN109415319A CN 109415319 A CN109415319 A CN 109415319A CN 201780042463 A CN201780042463 A CN 201780042463A CN 109415319 A CN109415319 A CN 109415319A
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CN
China
Prior art keywords
alkyl
catalyst
alkoxy
aryl
chloro
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Pending
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CN201780042463.6A
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English (en)
Chinese (zh)
Inventor
J·S·菲斯克
X·李
M·穆赫菲尔德
R·S·鲍曼
J·奥本海默
S·涂
M·A·尼兹
R·查克拉巴蒂
S·D·费斯特
J·W·林格
R·B·冷
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Corteva Agriscience LLC
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Dow AgroSciences LLC
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Publication of CN109415319A publication Critical patent/CN109415319A/zh
Pending legal-status Critical Current

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    • 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

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  • 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)
CN201780042463.6A 2016-05-19 2017-05-19 通过直接苏楚基偶联合成芳基羧酸酯 Pending CN109415319A (zh)

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
CN109415319A true CN109415319A (zh) 2019-03-01

Family

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CN201780042463.6A Pending CN109415319A (zh) 2016-05-19 2017-05-19 通过直接苏楚基偶联合成芳基羧酸酯

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=)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115551833A (zh) * 2020-05-11 2022-12-30 科迪华农业科技有限责任公司 具有杀有害生物活性的化合物的制备
CN115819334A (zh) * 2022-06-28 2023-03-21 安徽众邦生物工程有限公司 一种氯氟吡啶酯的制备方法

Families Citing this family (6)

* Cited by examiner, † Cited by third party
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
WO2023248174A1 (en) * 2022-06-22 2023-12-28 Hetero Labs Limited An improved process for preparation of voxelotor

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1551876A (zh) * 2001-07-30 2004-12-01 �ݶ�ũ�����޹�˾ 6-芳基-4-氨基吡啶甲酸酯及其作为除草剂的用途
CN101883759A (zh) * 2007-10-02 2010-11-10 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
CN102066336A (zh) * 2008-04-18 2011-05-18 陶氏益农公司 2-(取代的苯基)-6-羟基或烷氧基-5-取代的-嘧啶-4-羧酸酯和它们作为除草剂的用途
US20130172566A1 (en) * 2011-12-30 2013-07-04 Dow Agrosciences Llc Methods of producing methyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylate
CN103429081A (zh) * 2011-01-25 2013-12-04 陶氏益农公司 制备4-氨基-5-氟-3-卤代-6-(取代的)吡啶-2-甲酸酯的方法
CN103429082A (zh) * 2011-01-25 2013-12-04 陶氏益农公司 4-氨基-3-氯-5-氟-6-(取代的)吡啶-2-甲酸酯的制备方法
CN104093311A (zh) * 2011-01-25 2014-10-08 陶氏益农公司 作为除草剂的6-氨基-2-取代的-5-乙烯基甲硅烷基嘧啶-4-甲酸及酯和4-氨基-6-取代的-3-乙烯基甲硅烷基吡啶-2-甲酸及酯
CN104640844A (zh) * 2012-07-24 2015-05-20 美国陶氏益农公司 4-氨基-5-氟-3-卤代-6-(取代的)吡啶-2-甲酸酯的制备方法
CN105209451A (zh) * 2013-03-15 2015-12-30 美国陶氏益农公司 4-氨基-6-(杂环基)吡啶-2-甲酸酯和6-氨基-2-2(杂环基)嘧啶-4-羧酸酯和它们作为除草剂的用途
CN105209452A (zh) * 2013-03-15 2015-12-30 美国陶氏益农公司 4-氨基-6-(杂环基)吡啶-2-甲酸酯和6-氨基-2-(杂环基)嘧啶-4-羧酸酯以及它们作为除草剂的用途

Family Cites Families (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
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）
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
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
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
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

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1551876A (zh) * 2001-07-30 2004-12-01 �ݶ�ũ�����޹�˾ 6-芳基-4-氨基吡啶甲酸酯及其作为除草剂的用途
CN101883759A (zh) * 2007-10-02 2010-11-10 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
CN102066336A (zh) * 2008-04-18 2011-05-18 陶氏益农公司 2-(取代的苯基)-6-羟基或烷氧基-5-取代的-嘧啶-4-羧酸酯和它们作为除草剂的用途
CN103429081A (zh) * 2011-01-25 2013-12-04 陶氏益农公司 制备4-氨基-5-氟-3-卤代-6-(取代的)吡啶-2-甲酸酯的方法
CN103429082A (zh) * 2011-01-25 2013-12-04 陶氏益农公司 4-氨基-3-氯-5-氟-6-(取代的)吡啶-2-甲酸酯的制备方法
CN104093311A (zh) * 2011-01-25 2014-10-08 陶氏益农公司 作为除草剂的6-氨基-2-取代的-5-乙烯基甲硅烷基嘧啶-4-甲酸及酯和4-氨基-6-取代的-3-乙烯基甲硅烷基吡啶-2-甲酸及酯
US20130172566A1 (en) * 2011-12-30 2013-07-04 Dow Agrosciences Llc Methods of producing methyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylate
CN104640844A (zh) * 2012-07-24 2015-05-20 美国陶氏益农公司 4-氨基-5-氟-3-卤代-6-(取代的)吡啶-2-甲酸酯的制备方法
CN105209451A (zh) * 2013-03-15 2015-12-30 美国陶氏益农公司 4-氨基-6-(杂环基)吡啶-2-甲酸酯和6-氨基-2-2(杂环基)嘧啶-4-羧酸酯和它们作为除草剂的用途
CN105209452A (zh) * 2013-03-15 2015-12-30 美国陶氏益农公司 4-氨基-6-(杂环基)吡啶-2-甲酸酯和6-氨基-2-(杂环基)嘧啶-4-羧酸酯以及它们作为除草剂的用途

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115551833A (zh) * 2020-05-11 2022-12-30 科迪华农业科技有限责任公司 具有杀有害生物活性的化合物的制备
CN115819334A (zh) * 2022-06-28 2023-03-21 安徽众邦生物工程有限公司 一种氯氟吡啶酯的制备方法

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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
CA3023935A1 (en) 2017-11-23
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
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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