Diisopropylethylamine → 4-bromo-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine

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Reaction Steps

A mixture of 4-bromo-1H-pyrrolo[2,3-b]pyridine (1.00 g, 5.08 mmol), SEMCl (0.898 mL, 5.08 mmol) and DIPEA (1.768 mL, 10.15 mmol) in DCM (20.0 mL) was stirred at RT. After 3 nights the mixture was evaporated to dryness. The residues were purified on silica eluting with isohexane and ethyl acetate (0-100%). The appropriate fractions were combined and evaporated to dryness producing the title compound (1.65 g). LCMS (A): m/z (M+H)+ 327/329, C13H19BrN2OSi requires 326/328 (basic).

Provenance & Evidence