Iodine → 3-Iodo-7-azaindole

Participants

Reaction Conditions

Reaction Steps

A solution of 7-azaindole (20.0 g, 169 mmol) in ethanol is treated with iodine (57.9 g, 228 mmol), potassium iodide (37.8 g, 228 mmol), and 1 N aqueous NaOH (204 mL, 204 mmol). After stirring for 4 h at 20° C., the reaction is diluted with water and extracted with ethyl acetate. The organic extracts are combined and concentrated in vacuo. The resultant residue is crystallized from methanol/water to afford the title compound as a pinkish-white solid, 35.4 g, mp 201-204° C., characterized by mass spectral and HNMR analyses.

Provenance & Evidence