5-Chloro-2-cyanophenylboronic acid → 4-Chloro-2-(5-ethoxy-2-methoxypyridin-4-yl)benzonitrile

HRID 56851Notes

Reaction equation

HRID 56851 reaction equation
[CH2:1]([O:3][C:4]1[C:5](I)=[CH:6][C:7]([O:10][CH3:11])=[N:8][CH:9]=1)[CH3:2].[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:5]2[C:4]([O:3][CH2:1][CH3:2])=[CH:9][N:8]=[C:7]([O:10][CH3:11])[CH:6]=2)[CH:19]=1

Participants

3

Reactant 2

HCID 467389345-Chloro-2-cyanophenylboronic acidHCID 1176054865-Ethoxy-4-iodo-2-methoxypyridine

Product 1

HCID 1176049684-Chloro-2-(5-ethoxy-2-methoxypyridin-4-yl)benzonitrile

Procedure

322 mg (purity 93%, 1.07 mmol) of 5-ethoxy-4-iodo-2-methoxypyridine and 234 mg (1.29 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 (silica gel 50, cyclohexane/ethyl acetate gradient). Yield: 135 mg (41% of theory)

Workup

  1. customThe crude product was purified by flash chromatography (silica gel 50, cyclohexane/ethyl acetate gradient)

Sources & evidence

ORD record
ord-92844939f5a14b539b19f8cf2c1cf435
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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