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 PDF

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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
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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
Application number
CA3023935A
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English (en)
French (fr)
Inventor
Jason S. FISK
Xiaoyong Li
Mark MUEHLFELD
Robert S. BAUMAN
Jossian Oppenheimer
Siyu TU
Mark A. Nitz
Reetam Chakrabarti
Shawn D. Feist
James W. Ringer
Ronald B. Leng
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Corteva Agriscience LLC
Original Assignee
Dow AgroSciences LLC
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Filing date
Publication date
Application filed by Dow AgroSciences LLC filed Critical Dow AgroSciences LLC
Publication of CA3023935A1 publication Critical patent/CA3023935A1/en
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)
CA3023935A 2016-05-19 2017-05-19 Synthesis of 6-aryl-4-aminopicolinates and 2-aryl-6-aminopyrimidine-4-carboxylates by direct suzuki coupling Pending CA3023935A1 (en)

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 (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)

* 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
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
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
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
EP4149926A1 (en) * 2020-05-11 2023-03-22 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

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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
WO2007082076A1 (en) * 2006-01-13 2007-07-19 Dow Agrosciences Llc 2-(poly-substituted aryl)-6-amino-5-halo-4-pyrimidinecarboxylic acids and their use as herbicides
EP2311815B1 (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
AU2008293462B2 (en) * 2007-08-30 2013-08-15 Corteva Agriscience Llc 2-(substituted phenyl)-6-amino-5-alkoxy, thioalkoxy and aminoalkyl-4-pyrimidinecarboxylates and their use as herbicides
PL2327694T3 (pl) * 2007-10-02 2013-12-31 Dow Agrosciences Llc Podstawione kwasy 4-aminopikolinowe i ich zastosowanie jako herbicydów
MX2010011468A (es) * 2008-04-18 2010-12-14 Dow Agrosciences Llc 2-(fenil substituido)-6-hidroxi o alcoxi-5-substituido-4-pirimidin carboxilatos y sus usos como herbicidas.
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
CA2825392C (en) * 2011-01-25 2016-10-25 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
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）
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
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）
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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
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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
WO2014151008A1 (en) * 2013-03-15 2014-09-25 Dow Agrosciences Llc 4-amino-6-(heterocyclic)picolinates and 6-amino-2-(heterocyclic)pyrimidine-4-carboxylates and their use as herbicides
EP2967057B1 (en) * 2013-03-15 2018-11-21 Dow AgroSciences LLC Novel 4-aminopyridine and 6-aminopyrimidine carboxylates 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

Also Published As

Publication number Publication date
JP2019516708A (ja) 2019-06-20
RU2018144344A3 (enExample) 2021-02-18
IL263075A (en) 2018-12-31
EP3458442A1 (en) 2019-03-27
KR20190007048A (ko) 2019-01-21
BR112018073348B1 (pt) 2023-01-24
JP7113762B2 (ja) 2022-08-05
WO2017201377A1 (en) 2017-11-23
US10570114B2 (en) 2020-02-25
US20180334445A1 (en) 2018-11-22
AU2017268424B2 (en) 2021-07-15
US20170334878A1 (en) 2017-11-23
US20180334444A1 (en) 2018-11-22
MX2018014174A (es) 2019-03-14
AU2021203233A1 (en) 2021-06-10
EP3458442B1 (en) 2022-12-28
US10087164B2 (en) 2018-10-02
AU2017268424A1 (en) 2018-11-22
BR112018073348A2 (pt) 2019-03-06
BR112018073348B8 (pt) 2023-05-16
US10544121B2 (en) 2020-01-28
JP2022141912A (ja) 2022-09-29
EP3458442A4 (en) 2020-04-22
RU2018144344A (ru) 2020-06-19
NZ747932A (en) 2022-03-25
CN109415319A (zh) 2019-03-01

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