Methyl iodide → 5-fluoro-1-methyl-1H-indole-3-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

In DMF (60 ml) was dissolved 5-fluoroindole-3-carbaldehyde (5.00 g, 30.6 mmol). Under stirring at 0° C., sodium hydride (60% in oil, 1.35 g, 33.7 mmol) was added in portions. After the reaction mixture was stirred at the same temperature for 1 hour, methyl iodide (5.72 ml, 91.9 mmol) was added thereto. The resulting mixture was stirred further at 0° C. for 2 hours. A saturated aqueous solution of ammonium chloride was added to the reaction mixture to neutralize the same, followed by extraction with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from ethyl acetate eluate fractions, 5-fluoro-1-methylindole-3-carbaldehyde (5.42 g, 100%) was obtained as a colorless solid.

Provenance & Evidence