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

Participants

Reaction Steps

A solution of 6-Bromoindole (1 g, 5 mmol) in DMF (3 ml) was added to a suspension of NaH (134.7 mg, 5.6 mmol) in DMF (98 ml) at 0° C. and stirred for 15 mins. Triisopropylsilyl chloride (1.082 g, 5.6 mmol) was added dropwise, and the reaction mixture stirred for 2 h before being poured into ice-water and extracted with ethyl acetate. The organic layer was washed with brine, concentrated in vacuo and the crude product passed through a silica gel column, eluting with hexanes, to give the title compound (406.7 mg, 23%) as a colourless oil.

Provenance & Evidence