Sodium hydride → 1-(7-Ethoxycarbonylheptyl)-2-(1-imidazolyl)-3-methylindole

Participants

Reaction Steps

3-Methyl-2-(1-imidazolyl)indole (0.78 g) in dimethylformamide (8 ml) is added dropwise to a suspension of sodium hydride (50% dispersion in mineral oil, 0.20 g) in dimethylformamide (8 ml) stirred under nitrogen at 5°-10°. The resulting solution is stirred at 5°-10° for 1/2 hour. A solution of ethyl 8-bromooctanoate (1.00 g) in dimethylformamide (5 ml) is added dropwise. The reaction mixture is stirred at 5°-10° for 1/2 hour and then overnight at room temperature. The mixture is diluted with water (50 ml) and extracted into methylene chloride (3×25 ml). The extract is washed with water and saturated aqueous sodium chloride solution, dried over MgSO4, filtered, and concentrated in vacuo to give a two-phase oil. This oil is dissolved in ether (50 ml) and the solution is washed with water (5×25 ml) to remove dimethylformamide. The ether layer is dried over MgSO4, filtered, and concentrated in vacuo to give 1-(7-ethoxycarbonylheptyl)-2-(1-imidazolyl)-3-methylindole a viscous oil; NMR (CDCl3): δ 4.12 (q, 2H), 3.82 (t, 2H), 2.20 (s, 3H), 1.23 (t, 3H).

Provenance & Evidence