Methyl iodide → Methyl 6-bromo-1-methyl-1H-indole-3-carboxylate

Participants

Reaction Steps

To a mixture of 25 g (98.39 mmol) of 6-bromo-1H-indole-3-carboxylic acid methyl ester and 27.20 g (196 mmol) of potassium carbonate in 300 mL of acetonitrile is added at room temperature Methyl Iodide (20.95 g, 147.6 mmol). The reaction mixture is stirred at room temperature for 3 days. The solvent is evaporated, 500 ml of water is added, and the organic layer is extracted with (3×300 ml) ethyl acetate. The organics are combined, dried over magnesium sulfate and evaporated. The crude is purified by silica gel chromatography eluting with hex/EtOAc 8:2. The title compound (23.3 g (88%)) is obtained as a brown solid. MS (m/e): 268 (M+1).

Provenance & Evidence