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

HRID 56856Notes

Reaction equation

HRID 56856 reaction equation
[F:1][CH:2]([F:13])[O:3][C:4]1[C:5](I)=[CH:6][C:7]([O:10][CH3:11])=[N:8][CH:9]=1.[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([C:24]#[N:25])=[C:19](B(O)O)[CH:20]=1>>[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([C:24]#[N:25])=[C:19]([C:5]2[C:4]([O:3][CH:2]([F:13])[F:1])=[CH:9][N:8]=[C:7]([O:10][CH3:11])[CH:6]=2)[CH:20]=1

Participants

3

Reactant 2

HCID 467389345-Chloro-2-cyanophenylboronic acidHCID 1176053175-(Difluoromethoxy)-4-iodo-2-methoxypyridine

Product 1

HCID 1176057244-Chloro-2-[5-(difluoromethoxy)-2-methoxypyridin-4-yl]benzonitrile

Procedure

460 mg (purity 90%, 1.38 mmol) of 5-(difluoromethoxy)-4-iodo-2-methoxypyridine and 299 mg (1.65 mmol, 1.2 eq.) 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. The crude product was purified by flash chromatography (IR-50SI, petroleum ether/ethyl acetate 10-15%). Yield: 230 mg (purity 80%, 43% of theory)

Workup

  1. customThe crude product was purified by flash chromatography (IR-50SI, petroleum ether/ethyl acetate 10-15%)

Sources & evidence

ORD record
ord-06c49ecf66fc4c2ca0524010c4bd3825
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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