MX2018014174A - Sintesis de 6-aril-4-aminopicolinatos y 2-aril-6-aminopirimidin-4- carboxilatos mediante acoplamiento suzuki directo. - Google Patents

Sintesis de 6-aril-4-aminopicolinatos y 2-aril-6-aminopirimidin-4- carboxilatos mediante acoplamiento suzuki directo.

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Publication number
MX2018014174A
MX2018014174A MX2018014174A MX2018014174A MX2018014174A MX 2018014174 A MX2018014174 A MX 2018014174A MX 2018014174 A MX2018014174 A MX 2018014174A MX 2018014174 A MX2018014174 A MX 2018014174A MX 2018014174 A MX2018014174 A MX 2018014174A
Authority
MX
Mexico
Prior art keywords
aryl
carboxylates
chloro
fluoro
aminopicolinates
Prior art date
Application number
MX2018014174A
Other languages
English (en)
Inventor
S Fisk Jason
Li Xiaoyong
Chakrabarti Reetam
B Leng Ronald
Muehlfeld Mark
S Bauman Robert
Oppenheimer Jossian
Tu Siyu
D Feist Shawn
W Ringer James
A Nitz Mark
Original Assignee
Dow Agrosciences Llc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Dow Agrosciences Llc filed Critical Dow Agrosciences Llc
Publication of MX2018014174A publication Critical patent/MX2018014174A/es

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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)

Abstract

En la presente se describen métodos mejorados para la síntesis de 6-aril-4-aminopicolinatos, tales como arilalquilo y 4-amino-3-cloro-6-(4-cloro-2-fluoro-3-metoxifenil)piridina-2-carb oxilatos de alquilo y 4-amino-3-cloro-5-fluoro-6-(4-cloro-2-fluoro -3-metoxifenil)piridina-2-carboxilatos de alquilo y arilalquilo. Los métodos mejorados incluyen una etapa de acopamiento Suzuki directo, que elimina las etapas de protección/desprotección en los procesos químicos actuales y, por lo tanto, elimina o reduce las diversas materias primas, equipos y tiempos de ciclo, así como la modificación de otras condiciones de los procesos que incluyen el uso de AP bruta, uso de ABA-diMe, y variación del pH, concentración del catalizador, composición del solvente y/o procedimientos de tratamiento. La presente invención se amplió para que incluya la síntesis de 2-aril-6-aminopirimidina-4-carboxi latos.
MX2018014174A 2016-05-19 2017-05-19 Sintesis de 6-aril-4-aminopicolinatos y 2-aril-6-aminopirimidin-4- carboxilatos mediante acoplamiento suzuki directo. MX2018014174A (es)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201662338562P 2016-05-19 2016-05-19
US201662416811P 2016-11-03 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
MX2018014174A true MX2018014174A (es) 2019-03-14

Family

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Family Applications (1)

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MX2018014174A MX2018014174A (es) 2016-05-19 2017-05-19 Sintesis de 6-aril-4-aminopicolinatos y 2-aril-6-aminopirimidin-4- carboxilatos mediante acoplamiento suzuki directo.

Country Status (12)

Country Link
US (3) US10087164B2 (es)
EP (1) EP3458442B1 (es)
JP (2) JP7113762B2 (es)
KR (1) KR20190007048A (es)
CN (1) CN109415319A (es)
AU (2) AU2017268424B2 (es)
BR (1) BR112018073348B8 (es)
CA (1) CA3023935A1 (es)
IL (1) IL263075A (es)
MX (1) MX2018014174A (es)
RU (1) RU2018144344A (es)
WO (1) WO2017201377A1 (es)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2017268424B2 (en) * 2016-05-19 2021-07-15 Corteva Agriscience Llc Synthesis of 6-aryl-4-aminopicolinates and 2-aryl-6-aminopyrimidine-4-carboxylates by direct suzuki coupling
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
EP4121416A1 (en) 2020-03-18 2023-01-25 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

Family Cites Families (18)

* Cited by examiner, † Cited by third party
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
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
MX2010003464A (es) * 2007-10-02 2010-04-27 Dow Agrosciences Llc Acidos 2-substituido-6-amino-5-alquilo, alquenilo o alquinilo-4-pirimidinacarboxilico y acidos picolinicos 6-substituido-4-amino-3-alquilo, alquenilo o alquinilo y su uso como herbicidas.
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
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
EP2667717A4 (en) 2011-01-25 2015-10-14 Dow Agrosciences Llc 6-AMINO-2-SUBSTITUTED-5-VINYLSILYLPYRIMIDIN-4-CARBOXYLIC ACIDS AND ESTERS AND 4-AMINO-6-SUBSTITUTED-3-VINYLSILYLPYRIDINE-2-CARBOXYLIC ESTERS AS HERBICIDES
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）
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
IN2014DN05767A (es) 2011-12-30 2015-04-10 Dow Agrosciences Llc
BR112014016049B8 (pt) 2011-12-30 2022-10-11 Dow Agrosciences Llc Métodos para produção, síntese, isolamento e uso de (4-cloro-2-flúor-3-substituído-fenil)boronatos
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
KR102305436B1 (ko) * 2013-03-15 2021-09-27 코르테바 애그리사이언스 엘엘씨 4-아미노-6-(헤테로시클릭)피콜리네이트 및 6-아미노-2-(헤테로시클릭)피리미딘-4-카르복실레이트 및 제초제로서의 그의 용도
JP6513073B2 (ja) 2013-03-15 2019-05-15 ダウ アグロサイエンシィズ エルエルシー ４−アミノ−６−（複素環式）ピコリネートおよび６−アミノ−２−（複素環式）ピリミジン−４−カルボキシレートならびに除草剤としてのそれらの使用
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
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
AU2017268424B2 (en) * 2016-05-19 2021-07-15 Corteva Agriscience 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
BR112018073348B8 (pt) 2023-05-16
EP3458442A4 (en) 2020-04-22
BR112018073348B1 (pt) 2023-01-24
US10087164B2 (en) 2018-10-02
US20170334878A1 (en) 2017-11-23
CA3023935A1 (en) 2017-11-23
IL263075A (en) 2018-12-31
JP2019516708A (ja) 2019-06-20
US10570114B2 (en) 2020-02-25
JP2022141912A (ja) 2022-09-29
US10544121B2 (en) 2020-01-28
CN109415319A (zh) 2019-03-01
NZ747932A (en) 2022-03-25
KR20190007048A (ko) 2019-01-21
AU2017268424A1 (en) 2018-11-22
JP7113762B2 (ja) 2022-08-05
US20180334444A1 (en) 2018-11-22
EP3458442A1 (en) 2019-03-27
RU2018144344A (ru) 2020-06-19
WO2017201377A1 (en) 2017-11-23
AU2017268424B2 (en) 2021-07-15
AU2021203233A1 (en) 2021-06-10
BR112018073348A2 (pt) 2019-03-06
EP3458442B1 (en) 2022-12-28
US20180334445A1 (en) 2018-11-22
RU2018144344A3 (es) 2021-02-18

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