Indole → HCID 21260630, compound

Participants

Reaction Steps

Under argon, a dimethylformamide (50 ml) solution of indole (18 g) was added into dimethylformamide (350 ml) in which 60% sodium hydride (7.9 g) was suspended, and the mixture was stirred at room temperature for 30 minutes. A dimethylformamide (100 ml) solution of 3-chloromethylpyridine hydrochloride (25 g) was added at 0° C. and the mixture stirred at room temperature for 18 hours. After the reaction, a saturated aqueous sodium hydrogencarbonate solution was added at 0° C. and the mixture was extracted with ethyl acetate. The organic phase was washed with brine and dried over magnesium sulfate, then the solvent was evaporated in vacuo and the residue was purified by silica gel column chromatography to obtain 1-(3-pyridylmethyl)indole (31.9 g).

Provenance & Evidence