Dimethylformamide → N-(1-Cyanoisoquinolin-5-yl)-N'-[4(trifluoromethyl)benzyl]urea

Participants

Reaction Steps

To a solution of N-(1-chloroisoquinolin-5-yl)-N′-[4-(trifluoromethyl)benzyl]urea (Example 69) (250 mg, 0.7 mmol) in DMF (5 ml) was added zinc cyanide (43 mg, 0.37 mmol) and tetrakis(triphenylphosphine)palladium (76 mg, 0.07 mmol). The reaction was heated at 80° C., under an atmosphere of nitrogen, for 72 hr, with the addition of extra tetrakis(triphenylphosphine)palladium (76 mg, 0.07 mmol) after 16 hr. Reaction mixture was quenched with water and extracted with ethyl acetate (3×5 ml), dried over MgSO4 and evaporated. The residue was purified by flash column chromatography using an eluant system of 3% methanol/97% DCM increasing to 5% MeOH/95% DCM. Recrystallisation in ethanol of a small portion of product gave a pure sample of the title compound (50 mg, 65.6%). m/z (ES+) 371, 373 (M+H)+.

Provenance & Evidence