(3,4-Difluoro-2-methoxyphenyl)boronic acid → N-[4-(3,4-Difluoro-2-methoxy-phenyl)-pyridin-3-yl]-N-methyl-3,5-bis-trifluoromethyl-benzamide

HRID 878040Notes

Reaction equation

HRID 878040 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N:8]([CH3:25])[C:9](=[O:24])[C:10]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[C:12]([C:20]([F:23])([F:22])[F:21])[CH:11]=1.[CH3:26][O:27][C:28]1[C:33]([F:34])=[C:32]([F:35])[CH:31]=[CH:30][C:29]=1B(O)O>>[F:34][C:33]1[C:28]([O:27][CH3:26])=[C:29]([C:2]2[CH:7]=[CH:6][N:5]=[CH:4][C:3]=2[N:8]([CH3:25])[C:9](=[O:24])[C:10]2[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[C:12]([C:20]([F:23])([F:22])[F:21])[CH:11]=2)[CH:30]=[CH:31][C:32]=1[F:35]

Participants

3

Reactant 2

HCID 53216751(3,4-Difluoro-2-methoxyphenyl)boronic acidHCID 86670692N-(4-bromo-pyridin-3-yl)-N-methyl-3,5-bis-trifluoromethyl-benzamide

Product 1

HCID 86670707N-[4-(3,4-Difluoro-2-methoxy-phenyl)-pyridin-3-yl]-N-methyl-3,5-bis-trifluoromethyl-benzamide

Procedure

The title compound was prepared in analogy to example 58, from N-(4-bromo-pyridin-3-yl)-N-methyl-3,5-bis-trifluoromethyl-benzamide (example 25, intermediate a) and 2-methoxy-3,4-difluorophenylboronic acid (CAS RN 905583-06-4) and using preparative HPLC for the chromatographic purification. Off-white solid (49%). MS (ESI): m/z=491.1 [M+H]+.

Workup

  1. customfor the chromatographic purification

Sources & evidence

ORD record
ord-46c88e0c06844e58a3a1381fc408a965
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

Loading…