Sodium hydride → 5-Bromo-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine

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Reaction Steps

Sodium hydride (0.63 g, 25.15 mol) was added in small portion to a stirred solution of 5-bromo-7-azaindole (3.3 g, 16.75 mmol) in THF (50 mL) at room temperature and the resulting suspension was stirred at room temperature for 15 min. Triisopropylsilyl chloride (5.3 mL, 25.15 mmol) was added and the mixture was heated at 80° C. for 3 h. The solvent was evaporated and the residue was dissolved in water (50 mL). The aqueous layer was extracted with EtOAc (3×50 mL), dried (Na2SO4) and concentrated under reduced pressure. The crude product was purified by Biotage HPFC system (10% EtOAc/Hexane) to afford the desired 5-bromo-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine as a white solid (5.2 g, 88%); Mass Spec 355 (M+1).

Provenance & Evidence