Methyl 4-iodo-3-phenylisothiazole-5-carboxylate → Methyl 4-cyano-3-phenylisothiazole-5-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 4-iodo-3-phenylisothiazole-5-carboxylate (Preparation 103D, 600 mg, 1.738 mmol) in NMP (2 mL) was added copper cyanide (311 mg, 3.48 mmol). The resulting mixture was heated at 100° C. in a microwave reactor for 45 min. The reaction mixture was diluted with EtOAc (40 mL), filtered, washed with water (2×20 mL), brine (10 mL) and concentrated. Flash chromatography gave methyl 4-cyano-3-phenylisothiazole-5-carboxylate (360 mg, 1.474 mmol, 85% yield) as a white solid. The compound had an LC/MS M+1=245.1.

Provenance & Evidence