Sodium hydride → 2-(2-tetrahydrofuranyl)-5-methanesulfonyl-1-(4-fluorobenzyl)-1H-indole

Participants

Reaction Steps

To a solution of the compound obtained in Example 13 (2) (113 mg) in N,N-dimethylformamide (5 ml), 60% sodium hydride (25.6 mg) was added under nitrogen atmosphere at 0° C. and the mixture was stirred for 30 minutes, followed by addition of 4-fluorobenzyl bromide (121 mg), and the mixture was stirred for 1 hour. The reaction solution was then poured into a saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous NaCl solution, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was separated using silica gel preparative thin-layer chromatography (hexane:ethyl acetate=1:1) to obtain 139 mg of the desired product as a white powder.

Provenance & Evidence