Dichloromethane → HCID 67349699, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 3-(6-chloropyridin-3-yl)-2,2-dimethyl-3-phenylpropanoate (0.11 g, 0.38 mmol), zinc cyanide (45 mg, 0.38 mmol), zinc (5 mg, 0.08 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (14 mg, 0.019 mmol), and N,N-dimethylacetamide (0.5 mL) was stirred at 120° C. under argon for 2 hr. The reaction mixture was concentrated under reduced pressure and the residue was partitioned between saturated aqueous sodium bicarbonate solution (10 mL) and ethyl acetate (20 mL). The aqueous layer was separated and extracted with ethyl acetate (10 mL). The combined organic solutions were dried (Na2SO4) and concentrated. Silica gel flash chromatography (0-100% ethyl acetate in hexanes) gave methyl 3-(6-cyanopyridin-3-yl)-2,2-dimethyl-3-phenylpropanoate (70 mg, 0.24 mmol, 63% yield) as a colorless solid. MS found: (M+H)+=295.27.

Provenance & Evidence