2-Bromo-4-chlorobenzonitrile → 4-Chloro-2-[2-methoxy-5-(trifluoromethyl)pyridin-4-yl]benzonitrile

HRID 56731

Reaction equation

HRID 56731 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7](B(O)O)[C:6]([C:12]([F:15])([F:14])[F:13])=[CH:5][N:4]=1.Br[C:17]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:18]=1[C:19]#[N:20]>>[Cl:25][C:23]1[CH:24]=[CH:17][C:18]([C:19]#[N:20])=[C:21]([C:7]2[C:6]([C:12]([F:15])([F:14])[F:13])=[CH:5][N:4]=[C:3]([O:2][CH3:1])[CH:8]=2)[CH:22]=1

Participants

3

Reactant 2

HCID 234985242-Bromo-4-chlorobenzonitrileHCID 1187044372-Methoxy-5-(trifluoromethyl)pyridine-4-boronic acid

Product 1

HCID 1176057584-Chloro-2-[2-methoxy-5-(trifluoromethyl)pyridin-4-yl]benzonitrile

Procedure

1.0 g (4.4 mmol) of 2-methoxy-5-trifluoromethylpyridin-4-ylboronic acid and 0.95 g (4.4 mmol) of 2-bromo-4-chlorobenzonitrile in the presence of [1,1-bis(diphenylphosphino)ferrocene]palladium(II) chloride/dichloromethane monoadduct were reacted according to General Method 2A. Yield: 351 mg (purity 71%, 18% of theory)

Sources & evidence

ORD record
ord-1fa0044468674d8d8fcdb79c4ca3d961
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Linked notes

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