5-Chloro-2-cyanophenylboronic acid → 4-Chloro-2-[2-methoxy-5-(2,2,2-trifluoroethoxy)pyridin-4-yl]benzonitrile

HRID 56861Notes

Reaction equation

HRID 56861 reaction equation
I[C:2]1[C:7]([O:8][CH2:9][C:10]([F:13])([F:12])[F:11])=[CH:6][N:5]=[C:4]([O:14][CH3:15])[CH:3]=1.[Cl:16][C:17]1[CH:18]=[CH:19][C:20]([C:26]#[N:27])=[C:21](B(O)O)[CH:22]=1>>[Cl:16][C:17]1[CH:18]=[CH:19][C:20]([C:26]#[N:27])=[C:21]([C:2]2[C:7]([O:8][CH2:9][C:10]([F:13])([F:12])[F:11])=[CH:6][N:5]=[C:4]([O:14][CH3:15])[CH:3]=2)[CH:22]=1

Participants

3

Reactant 2

HCID 467389345-Chloro-2-cyanophenylboronic acidHCID 1176057734-Iodo-2-methoxy-5-(2,2,2-trifluoroethoxy)pyridine

Product 1

HCID 1176048304-Chloro-2-[2-methoxy-5-(2,2,2-trifluoroethoxy)pyridin-4-yl]benzonitrile

Procedure

500 mg (purity 94%, 1.41 mmol) of 4-iodo-2-methoxy-5-(2,2,2-trifluoroethoxy)pyridine and 282 mg (1.55 mmol, 1.1 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: 168 mg (33% of theory)

Workup

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

Sources & evidence

ORD record
ord-18e6d29a66e342a7b89363ca8ae4b7ca
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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