5-Bromopentanenitrile → 3-(4-Cyanobutyl)-2-(3-pyridyl)indole

Participants

Reaction Steps

To 6.0 ml of a 2M solution of ethylmagnesium bromide in tetrahydrofuran under nitrogen at 0° is added dropwise over 20 minutes a solution of 2-(3-pyridyl)indole (1.9 g) in 12 ml of tetrahydrofuran. The mixture is stirred at 0° for 0.5 hour and is then treated with a solution of 1.78 g of 5-bromovaleronitrile in 4 ml of tetrahydrofuran. This mixture is stirred at 0° for 1 hour, then at room temperature for 1 hour, and is then poured into 125 ml of ice-water. This is extracted with 2×50 ml of ether, the extract is washed with water, dried, evaporated to dryness and purified to give 3-(4-cyanobutyl)-2-(3-pyridyl)indole.

Provenance & Evidence