Indole-3-acetonitrile → HCID 22607581, compound

Participants

Reaction Steps

A solution of 3-cyanomethylindole (156 mg, 1.0 mmol) in anhydrous ethanol (1.5 mL) at room temperature was treated with 21% sodium ethoxide in ethanol (450 μL), stirred for 1 hour, treated with 3-bromopyridine-5-carboxaldehyde (J. Heterocycl. Chem., 1995, 32, 1801.) (187 mg, 1.0 mmol), stirred overnight, and concentrated. The residue was purified by flash column chromatography on silica gel with 2% methanol/dichloromethane to provide the desired product (52 mg, 16%). MS (DCI/NH3) m/e 325 (M+H)+.

Provenance & Evidence