AU2017268424B2 - 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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AU2017268424B2
AU2017268424B2 AU2017268424A AU2017268424A AU2017268424B2 AU 2017268424 B2 AU2017268424 B2 AU 2017268424B2 AU 2017268424 A AU2017268424 A AU 2017268424A AU 2017268424 A AU2017268424 A AU 2017268424A AU 2017268424 B2 AU2017268424 B2 AU 2017268424B2
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chloro
aryl
mmol
methyl
alkyl
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AU2017268424A
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AU2017268424A1 (en
Inventor
Robert S. BAUMAN
Reetam Chakrabarti
Shawn D. Feist
Jason S. FISK
Ronald B. Leng
Xiaoyong Li
Mark MUEHLFELD
Mark A. Nitz
Jossian Oppenheimer
James W. Ringer
Siyu TU
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Corteva Agriscience LLC
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Corteva Agriscience LLC
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Assigned to CORTEVA AGRISCIENCE LLC reassignment CORTEVA AGRISCIENCE LLC Request to Amend Deed and Register Assignors: DOW AGROSCIENCES LLC
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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)
AU2017268424A 2016-05-19 2017-05-19 Synthesis of 6-aryl-4-aminopicolinates and 2-aryl-6-aminopyrimidine-4-carboxylates by direct suzuki coupling Ceased AU2017268424B2 (en)

Priority Applications (1)

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AU2021203233A AU2021203233A1 (en) 2016-05-19 2021-05-20 Synthesis of 6-aryl-4-aminopicolinates and 2-aryl-6-aminopyrimidine-4-carboxylates by direct Suzuki coupling

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

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AU2021203233A Division AU2021203233A1 (en) 2016-05-19 2021-05-20 Synthesis of 6-aryl-4-aminopicolinates and 2-aryl-6-aminopyrimidine-4-carboxylates by direct Suzuki coupling

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AU2017268424A1 AU2017268424A1 (en) 2018-11-22
AU2017268424B2 true AU2017268424B2 (en) 2021-07-15

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AU2021203233A Abandoned AU2021203233A1 (en) 2016-05-19 2021-05-20 Synthesis of 6-aryl-4-aminopicolinates and 2-aryl-6-aminopyrimidine-4-carboxylates by direct Suzuki coupling

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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)

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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

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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
KR20190007048A (ko) 2019-01-21
EP3458442A4 (en) 2020-04-22
US20170334878A1 (en) 2017-11-23

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