Methyl iodide → 6-Fluoro-1-methyl-1h-indole

Participants

Reaction Steps

In an oven dried, nitrogen purged, 3 neck, 50 mL round bottom flask, 1.00 g (7.40 mmol) of 6-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 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 0.525 g of the title compound, 48% yield. MS, ES=; 1H NMR (DMSO-d6) δ 7.523-7.488 (m, 1H); 7.300-7.292 (m, 2H); 6.852-6.825 (m, 1H); 6.411-6.409 (m, 1H); 3.767 (s, 3H) ppm.

Provenance & Evidence