Methyl iodide → 5-Chloro-1-methylindole

Participants

Reaction Steps

In an oven dried, nitrogen purged, 3 neck, 50 mL round bottom flask, 1.00 g (6.60 mmol) of 5-chloroindole in 10 mL of dry dimethylformamide is reacted with 0.260 g (6.60 mmol) of 60% sodium hydride dispersed in mineral oil at room temperature for 4 h. 0.411 mL (6.60 mmol) of iodomethane is added and the reaction is allowed to stir at room temperature 15 h. The reaction is quenched with 50 mL of water, extracted 3×50 mL of ethyl acetate, dried (MgSO4), and concentrated. The crude product is purified by chromatography using hexanes:ethyl acetate as a solvent system to obtain 0.545 g of the title compound, 50% yield. MS, ES=166.0 (M+1); 1H NMR (DMSO-d6) δ 7.567-7.564 (m, 1H); 7.453-7.431 (m, 1H); 7.381-7.374 (m, 1H); 7.131-7.105 (m, 1H); 6.393-6.386 (m, 1H); 2.768 (s, 3H) ppm.

Provenance & Evidence