GENERAL METHOD: A mixture of CuI (0.6 mmol), 5-nitroindole (0.5 mmol), and phenylacetonitrile (0.6 mmol) in DMF (3.0 mL) was placed in air and reacted with stirring for 34 h at 100 °C, followed by cooling to room temperature. Upon completion of the reaction, the reaction mixture was quenched with 10 mL of water followed by extraction with dichloromethane (DCM, 3 x 10 mL). The organic layers were combined, washed with saturated aqueous sodium chloride solution and dried with anhydrous magnesium sulfate (MgSO). Finally, the solution was concentrated under reduced pressure and purified by column chromatography to afford the target product 5-nitroindole-3-carbonitrile.
