2-Bromo-4-chlorobenzonitrile → 4-Chloro-2-(2,5-dimethoxypyridin-4-yl)benzonitrile

HRID 56735

Reaction equation

HRID 56735 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7](B(O)O)[C:6]([O:12][CH3:13])=[CH:5][N:4]=1.Br[C:15]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:16]=1[C:17]#[N:18]>>[Cl:23][C:21]1[CH:22]=[CH:15][C:16]([C:17]#[N:18])=[C:19]([C:7]2[C:6]([O:12][CH3:13])=[CH:5][N:4]=[C:3]([O:2][CH3:1])[CH:8]=2)[CH:20]=1

Participants

3

Reactant 2

HCID 234985242-Bromo-4-chlorobenzonitrileHCID 748906632,5-Dimethoxypyridine-4-boronic acid

Product 1

HCID 1176052164-Chloro-2-(2,5-dimethoxypyridin-4-yl)benzonitrile

Procedure

7.87 g (purity 95%, 40.86 mmol) of 2,5-dimethoxypyridin-4-ylboronic acid and 8.85 g (40.86 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: 6.23 g (purity 92%, 51% of theory)

Sources & evidence

ORD record
ord-e22a23f4a69c40a29f6214214a1fd8be
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Linked notes

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