Sodium hydride → 6-bromo-1-(triisopropylsilyl)-1H-indole

Participants

Reaction Steps

To a solution of 6-bromo-1H-indole (2 g, 10.2 mmol) in THF (20 mL) at 0° C. was added 0.46 g of sodium hydride (12 mmol) in 3 portions. The mixture was stirred 30 min followed by addition of chlorotriisopropylsilane (2 g, 10.4 mmol). The reaction was allowed to warm to room temperature and stirring was continued overnight. The mixture was then poured into sat. aq. sodium bicarbonate and extracted with ethyl acetate. The organic phase was washed with brine, dried (magnesium sulfate) and concentrate under vacuum to afford the crude product as an orange oil that was purified by flash chromatography on silica gel using a 4:1 ethyl acetate/heptane mixture as the eluent. The purified product (2.8 g) was a light orange oil.

Provenance & Evidence