Water → 4-Chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine

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Reaction Steps

NaH (0.177 g, 4.42 mmol) was added to 4-chloro-1H-pyrrolo[2,3-b]pyridine (0.450 g, 2.95 mmol) in dimethylformamide (“DMF”; 5 mL) at 0° C. The reaction was then warmed to room temperature and stirred for 1 hour. The reaction was then cooled to 0° C. Chlorotriisopropylsilane (0.945 mL, 4.42 mmol) was added to the mixture. The reaction mixture was warmed to 70° C. and stirred for 2 hours. Next, the reaction was poured into water (50 mL) and extracted with DCM (3×50 mL). The combined organic fractions were dried (MgSO4), filtered and concentrated. The resulting residue was purified by column chromatography (10:1 hexanes:DCM) to give 4-chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine (0.55 g, 60.4% yield).

Provenance & Evidence