N-Iodosuccinimide → 5-Bromo-4-chloro-3-iodo-1H-pyrrolo[2,3-b]pyridine

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Reaction Conditions

Reaction Steps

5-Bromo-4-chloro-1H-pyrrolo[2,3-b]pyridine (5.19 g, 22.4 mmol) and N-iodosuccinimide (5.55 g, 24.6 mmol) were suspended in 100 mL acetone. The mixture was stirred at 23° C. for 2 h and diluted with 150 mL water and 20 mL of saturated sodium thiosulfate solution. The precipitate was filtered and residual water was removed by dissolving the solids in dry benzene and followed by evaporation (2×100 mL) to yield 5-Bromo-4-chloro-3-iodo-1H-pyrrolo[2,3-b]pyridine (7.68 g, 21.5 mmol, 96%). 1H NMR (500 MHz, DMSO-d6) δ 12.65 (bs, 1H), 8.45 (s, 1H), 7.87 (d, J=3 Hz, 1H). MS: m/z 356.8/358.8 (M+H+).

Provenance & Evidence