(5-Chloro-2-methoxypyridin-3-yl)boronic acid → N-(5-Chloro-2-methoxy-[3,4']bipyridinyl-3'-yl)-N-methyl-3,5-bis-trifluoromethyl-benzamide

HRID 878023Notes

Reaction equation

HRID 878023 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.[Cl:26][C:27]1[CH:28]=[C:29](B(O)O)[C:30]([O:33][CH3:34])=[N:31][CH:32]=1>CN(C=O)C>[Cl:26][C:27]1[CH:28]=[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)[C:30]([O:33][CH3:34])=[N:31][CH:32]=1

Participants

4

Reactant 2

HCID 44754881(5-Chloro-2-methoxypyridin-3-yl)boronic acidHCID 86670692N-(4-bromo-pyridin-3-yl)-N-methyl-3,5-bis-trifluoromethyl-benzamide

Product 1

HCID 60196804N-(5-Chloro-2-methoxy-[3,4']bipyridinyl-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 5-chloro-2-methoxypyridine-3-boronic acid (CAS RN 943153-22-8) and using DMF as reaction solvent. Off-white solid (28%). MS (ESI): m/z=490.0 [M+H]+.

Workup

  1. customas reaction solvent

Sources & evidence

ORD record
ord-4bc702e0365a4f7e8b45d741aff1248c
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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