5-Chloro-2-cyanophenylboronic acid → 4-Chloro-2-[5-(difluoromethyl)-2-methoxypyridin-4-yl]benzonitrile

HRID 56727Notes

Reaction equation

HRID 56727 reaction equation
[F:1][CH:2]([F:12])[C:3]1[C:4](I)=[CH:5][C:6]([O:9][CH3:10])=[N:7][CH:8]=1.[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([C:23]#[N:24])=[C:18](B(O)O)[CH:19]=1>>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([C:23]#[N:24])=[C:18]([C:4]2[C:3]([CH:2]([F:12])[F:1])=[CH:8][N:7]=[C:6]([O:9][CH3:10])[CH:5]=2)[CH:19]=1

Participants

3

Reactant 2

HCID 467389345-Chloro-2-cyanophenylboronic acidHCID 1176057525-(Difluoromethyl)-4-iodo-2-methoxypyridine

Product 1

HCID 1176048794-Chloro-2-[5-(difluoromethyl)-2-methoxypyridin-4-yl]benzonitrile

Procedure

616 mg (purity 83%, 1.79 mmol) of 5-(difluoromethyl)-4-iodo-2-methoxypyridine and 325 mg (1.79 mmol) of 5-chloro-2-cyanophenylboronic acid in the presence of [1,1-bis(diphenylphosphino)ferrocene]palladium(II) chloride/dichloromethane monoadduct were reacted according to General Method 2A. Yield: 223 mg (42% of theory)

Sources & evidence

ORD record
ord-904989de005b4bff9637fe666df1165f
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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