Water → 1-Benzenesulfonyl-5-bromo-3-iodo-1H-pyrrolo[2,3-b]pyridine

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Reaction Steps

To a solution of 3-iodo-5-bromo-1H-pyrrolo[2,3-b]-pyridine (500 mg, 1.55 mmol) in CH2Cl2 (4.1 ml) are added 60% sodium hydride (186 mg, 4.66 mmol) and benzyltriethylammonium chloride (8 mg, 0.03 mmol) under argon at 0° C. After 30 minutes, benzenesulfonyl chloride (240 μl, 1.86 mmol) is added at 0° C. and the mixture is stirred at room temperature for 2 hours. The mixture is neutralized with water and extracted several times with CH2Cl2. The organic phases are combined, dried on MgSO4 and concentrated under reduced pressure. The residue is precipitated with methanol and the resulting solid filtered to yield the expected product in the form of a pink solid with 97% yield.

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