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

HRID 878019Notes

Reaction equation

HRID 878019 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.[F:26][C:27]1[C:28]([O:36][CH3:37])=[C:29](B(O)O)[CH:30]=[CH:31][CH:32]=1>CN(C=O)C>[F:26][C:27]1[C:28]([O:36][CH3:37])=[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][CH:32]=1

Participants

4

Reactant 2

HCID 21931617B-(3-Fluoro-2-methoxyphenyl)boronic acidHCID 86670692N-(4-bromo-pyridin-3-yl)-N-methyl-3,5-bis-trifluoromethyl-benzamide

Product 1

HCID 60196808N-[4-(3-Fluoro-2-methoxy-phenyl)-pyridin-3-yl]-N-methyl-3,5-bis-trifluoromethyl-benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared in analogy to example 25, from N-(4-bromo-pyridin-3-yl)-N-methyl-3,5-bis-trifluoromethyl-benzamide (example 25, intermediate a) and 3-fluoro-2-methoxyphenylboronic acid (CAS RN 762287-59-2) and using DMF as reaction solvent. Off-white solid (27%). MS (ESI): m/z=473.2 [M+H]+.

Workup

  1. customas reaction solvent

Sources & evidence

ORD record
ord-7555814c210c4ca999a604c8b3fef583
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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