US 12,281,076 B2
Process for synthesis of picolinamides
Nicholas R. Babij, Carmel, IN (US); Elizabeth O. McCusker, Carmel, IN (US); Gregory T. Whiteker, Carmel, IN (US); Neeraj Sane, Carmel, IN (US); Siyu Tu, Midland, MI (US); Xiaoyong Li, Zionsville, IN (US); Daniel W. Klosowski, Indianapolis, IN (US); Patrick T. McGough, Zionsville, IN (US); Meng Guo, Carmel, IN (US); Matthew Robinson, Indianapolis, IN (US); Jeffrey Scott Nissen, Indianapolis, IN (US); Tyler Davis, Carmel, IN (US); and Yan Hao, Zionsville, IN (US)
Assigned to CORTEVA AGRISCIENCE LLC, , IN (US)
Appl. No. 17/754,977
Filed by CORTEVA AGRISCIENCE LLC, Indianapolis, IN (US)
PCT Filed Oct. 15, 2020, PCT No. PCT/US2020/055658
§ 371(c)(1), (2) Date Apr. 18, 2022,
PCT Pub. No. WO2021/076681, PCT Pub. Date Apr. 22, 2021.
Claims priority of provisional application 62/923,235, filed on Oct. 18, 2019.
Prior Publication US 2022/0411375 A1, Dec. 29, 2022
Int. Cl. C07D 213/803 (2006.01); C07C 227/20 (2006.01)
CPC C07D 213/803 (2013.01) [C07C 227/20 (2013.01)] 13 Claims
 
1. A process for the preparation of the compound of Formula A

OG Complex Work Unit Chemistry
wherein Z is CH3CO, CH3CH2CO or (CH3)2CHCO;
from the compound of Formula B

OG Complex Work Unit Chemistry
wherein Z is CH3CO, CH3CH2CO or (CH3)2CHCO;
which comprises the steps of:
a) creating a first mixture containing the compound of Formula B, wherein Z is CH3CO, CH3CH2CO or (CH3)2CHCO, a coupling reagent, and a base;
b) adding at least one of the compounds of Formula C and Formula C1

OG Complex Work Unit Chemistry
wherein X is CI, Br, HSO4, H2PO4 or CH3SO3; to the first mixture to form a second mixture; and
c) isolating the compound of Formula A from the second mixture.