Methyl iodide → 5-fluoro-1-methylindole

Participants

Reaction Steps

In an oven dried, nitrogen purged, 3 neck, 50 mL round bottom flask, 1.00 g (7.40 mmol) of 5-fluoroindole in 10 mL of dry dimethylformamide is reacted with 0.335 g (8.88 mmol) of 60% sodium hydride dispersed in mineral oil at room temperature for 4 h. 0.553 mL (8.88 mmol) of iodomethane is added and the reaction is allowed to stir at room temperature overnight, 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 1.00 g of the title compound, 91% yield. MS, ES+218.2 (M+1); 1H NMR (DMSO-d6) δ 7.428-7.366 (m, 1H); 7.293-7.262 (m, 1H); 6.988-6.937 (m, 1H); 6.384-6.376 (m, 1H); 3.766 (s, 3H) ppm.

Provenance & Evidence