Iodine → 3-Iodo-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile

Participants

Reaction Conditions

Reaction Steps

To a solution of 35 (3.0 g, 21.0 mmol) in DMF (53 mL) was added KOH (4.35 g, 77.5 mmol, pellets) and the reaction mixture stirred for 20 min., cooled to 0° C., and treated with iodine (5.32 g, 21.0 mmol). It was stirred at room temperature for 50 min then poured onto a mixture of water (306 mL)/sat. aqueous Na2S2O3 (46 mL). The resulting solid was filtered off and washed with water (2×) to give 36 (3.57 g, 63%) as creamy solid; 1H NMR (400 MHz, DMSO) δ 7.96 (s), 8.25 (s), 8.64 (s), 12.74 (NH).

Provenance & Evidence