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

HRID 878028Notes

Reaction equation

HRID 878028 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[C:28]([O:36][CH3:37])=[N:29][CH:30]=[CH:31][C:32]=1B(O)O>CN(C=O)C>[Cl:26][C:27]1[C:28]([O:36][CH3:37])=[N:29][CH:30]=[CH:31][C:32]=1[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

Participants

4

Reactant 2

HCID 441198093-Chloro-2-methoxypyridine-4-boronic acidHCID 86670692N-(4-bromo-pyridin-3-yl)-N-methyl-3,5-bis-trifluoromethyl-benzamide

Product 1

HCID 86670701N-(3'-Chloro-2'-methoxy-[4,4']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 3-chloro-2-methoxypyridine-4-boronic acid (CAS RN 957060-88-7) and using DMF as solvent. Pale yellow sticky solid (11%). MS (ESI): m/z=489.9 [M+H]+.

Sources & evidence

ORD record
ord-e7c1b83006574e469d7dbbc9a1d5846e
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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