Iodine → 1H-Pyrrolo[2,3-b]pyridine, 3-iodo-5-(4-morpholinyl)-

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Reaction Steps

To a stirred solution of 53 (0.096 g, 0.47 mmol) in DMF (2 mL) was added solid KOH (85%, 0.112 g, 1.69 mmol). After 20 min iodine (0.132 g, 0.52 mmol) was added in one portion. After stirring for 1 hour the mixture was cooled with ice-water bath, and water (10 mL) followed by saturated aqueous Na2S2O3 solution (2 mL) were added. The precipitate was filtered off, washed with water and dried to afford 54 (0.102 g, 66%) as a brown solid. 1H NMR (400 MHz, CDCl3) δ 3.11-3.15 (m, 4H), 3.85-3.89 (m, 4H), 7.19 (d, J=0.26 Hz, 1H), 7.33 (d, J=0.24 Hz, 1H), 8.08 (d, J=0.26 Hz, 1H), 9.81 (bs, 1H).

Provenance & Evidence