Sodium hydride → HCID 22007016, compound

Participants

Reaction Steps

A solution of ethyl-2-indolecarboxylate (500 mg, 2.64 mmol) in dry THF (5 mL) under an argon atmosphere was cooled to 0° C. and treated with sodium hydride (116 mg, 2.90 mmol). After stirring at room temperature for 5 minutes, the reaction was cooled to 0° C. and treated with methanesulfonyl chloride (0.23 mL, 2.90 mmol). The resulting mixture was gradually warmed to room temperature and stirred for 20 h. The reaction was quenched with saturated NaHCO3 and diluted with ethyl acetate. The organic layer was washed with water and brine, dried over Na2SO4, and concentrated in vacuo. The resulting golden yellow oil was chromatographed over silica gel eluting with 5%, 10%, and 15% ethyl acetate/hexane to provide the title compound (79%, 556.6 mg) as a cream solid. 1H NMR (400 MHz, CDCl3) δ8.05 (d, 1H), 7.65 (d, 1H), 744 (t, 1H), 7.31 (m, 2H), 4.42 (q, 2H), 3.71 (s, 3H), 1.42 (t, 3H).

Provenance & Evidence