N-methyl-2-pyrrolidone → ethyl 5-cyano-6-methoxy-1H-indole-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of ethyl 5-bromo-6-methoxy-1H-indole-2-carboxylate obtained in step 1 (300 mg; 1.01 mmol) and cuprous cyanide (108 mg; 1.21 mmol) in NMP (10 mL) was heated under microwave irradiations at 200° C. for 30 minutes. The dark solution was filtered through a short pad of silica, which was washed with DCM. The obtained dark red solution was concentrated in vacuo and the oily residue was precipitated in water. The solid was collected by filtration, washed thoroughly with water and dried under high vacuum. Purification by silica column chromatography (DCM then DCM/MeOH, 99/1) gave the title compound as a slightly pink solid. HPLC (Method A), Rt 3.45 min (Purity: 97.4%). LC/MS (Method B): 243.2 (M+H)+.

Provenance & Evidence