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1. (WO2017201377) SYNTHESIS OF 6-ARYL-4-AMINOPICOLINATES AND 2-ARYL-6-AMINOPYRIMIDINE-4-CARBOXYLATES BY DIRECT SUZUKI COUPLING
Latest bibliographic data on file with the International Bureau    Submit observation

Pub. No.:    WO/2017/201377    International Application No.:    PCT/US2017/033489
Publication Date: 23.11.2017 International Filing Date: 19.05.2017
IPC:
C07D 213/803 (2006.01), C07F 5/02 (2006.01)
Applicants: DOW AGROSCIENCES LLC [US/US]; 9330 Zionsville Road Indianapolis, IN 46268 (US)
Inventors: FISK, Jason S.; (US).
LI, Xiaoyong; (US).
MUEHLFELD, Mark; (US).
BAUMAN, Robert S.; (US).
OPPENHEIMER, Jossian; (US).
TU, Siyu; (US).
NITZ, Mark A.; (US).
CHAKRABARTI, Reetam; (US).
FEIST, Shawn D.; (US).
RINGER, James W.; (US).
LENG, Ronald B.; (US)
Agent: TERAPANE, Michael; (US)
Priority Data:
62/338562 19.05.2016 US
62/416811 03.11.2016 US
Title (EN) SYNTHESIS OF 6-ARYL-4-AMINOPICOLINATES AND 2-ARYL-6-AMINOPYRIMIDINE-4-CARBOXYLATES BY DIRECT SUZUKI COUPLING
(FR) SYNTHÈSE DE 6-ARYL-4-AMINOPICOLINATES ET DE 2-ARYL-6-AMINOPYRIMIDINE-4-CARBOXYLATES PAR COUPLAGE DIRECT DE SUZUKI
Abstract: front page image
(EN)Improved methods of synthesizing 6-aryl-4-aminopicolinates, such as arylalky and alkyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylates and arylalkyl and alkyl 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2- carboxylates, are described herein. The improved methods include a direct Suzuki coupling step, which eliminates the protection/de-protection steps in the current chemical process, and therefore eliminates or reduces various raw materials, equipment and cycle time as well as modification of other process conditions including use of crude AP, use of ABA-diMe, and varying pH, catalyst concentration, solvent composition, and/or workup procedures. This invention was expanded to include synthesis of 2-aryl-6-aminopyrimidine-4-carboxylates.
(FR)L'invention concerne des procédés améliorés de synthèse de 6-aryl-4-aminopicolinates, tels que l'arylalkyle et l'alkyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-méthoxyphényl))pyridine-2-carboxylates et arylalkyle et alkyl 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-méthoxyphényl)pyridine-2-carboxylates. Les procédés améliorés comprennent une étape de couplage direct de Suzuki, qui élimine les étapes de protection/déprotection dans le processus chimique courant, et élimine ou réduit par conséquent diverses matières premières, l'équipement et le temps de cycle ainsi que la modification d'autres conditions de traitement, notamment l'utilisation d'AP brut, l'utilisation d'ABA-diMe, et la variation du pH, de la concentration du catalyseur, de la composition du solvant et/ou des procédures de travail. Cette invention a été étendue pour inclure la synthèse de 2-aryl-6-aminopyrimidine-4-carboxylates.
Designated States: AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DJ, DK, DM, DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IR, IS, JP, KE, KG, KH, KN, KP, KR, KW, KZ, LA, LC, LK, LR, LS, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW.
African Regional Intellectual Property Organization (BW, GH, GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, TZ, UG, ZM, ZW)
Eurasian Patent Organization (AM, AZ, BY, KG, KZ, RU, TJ, TM)
European Patent Office (AL, AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, SM, TR)
African Intellectual Property Organization (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, KM, ML, MR, NE, SN, TD, TG).
Publication Language: English (EN)
Filing Language: English (EN)