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

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Reaction Steps

To a solution of a 4:6 mixture of 1-benzenesulfonyl-5-bromo-4-chloro-2-iodo-1H-pyrrolo[2,3-b]pyridine and 5-bromo-4-chloro-2-iodo-1-(2-iodobenzenesulfonyl)-1H-pyrrolo[2,3-b]pyridine (100 mg, 0.178 mmol) in THF (4 mL) was added 3N NaOH in methanol (1 mL), and the mixture was stirred at RT for 30 min. The reaction was quenched with saturated ammonium chloride solution (2 mL), water (5 mL) was added, and the mixture was filtered. The precipitate obtained was washed with water (3×10 mL) followed by hexane (3×10 mL) and dried under vacuum to yield the title compound as white solid. 1H NMR (400 MHz, CD3OD): δ=8.21 (s, 1H), 6.74 (s, 1H); MS (ES+): m/z 358.75 (100) [MH+]; HPLC: tR=5.68 min (ZQ2000, nonpolar—15 min).

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