Indole → 1-(3-Bromo-4-methoxy-benzyl)-1H-indole

Participants

Reaction Steps

A solution of indole (250 mg, 2.14 mmol) in DMF (15 mL) was cooled in an ice bath. To this solution was added sodium hydride (64.3 mg, 2.68 mmol), followed by 2-Bromo-4-bromomethyl-1-methoxy-benzene (500 mg, 1.79 mmol). The reaction was warmed to room temperature and stirred overnight. To the reaction was added saturated aqueous ammonium chloride (75 mL) and the layers separated. The organic extract was washed with saturated aqueous ammonium chloride (2×75 mL), water (3×75 mL) and brine (50 mL). The extract was dried over sodium sulfate, and the solvent removed under reduced pressure. To residue was purified by flash silica gel column chromatography eluting with 1:3 hexanes: dichloromethane to give the title compound (I-107, X═CH) (490 mg, 87% yield) which was taken into further reactions.

Provenance & Evidence