Iodoethane → 1-ethyl-4-methyl-1H-indole-3-carbaldehyde

Participants

Reaction Steps

To a solution of 4-methyl-1H-indole-3-carbaldehyde (150 mg. 0.942 mmol) in dry DMF (1 mL) was added NaH (26 mg, 1.08 mmol) in 3 portions. When the evolution of gas was complete, the reaction vial was sealed and agitated for 5 m, after which time ethyl iodide (0.086 mL, 1.1 mmol) was added and agitation was continued overnight. The mixture was diluted with dichloromethane (10 mL), washed with water (2×5 mL), and brine (5 mL), dried and concentrated. This mixture was purified by flash chromatography using a gradient of ethyl acetate/hexane to provide 1-ethyl-4-methyl-1H-indole-3-carbaldehyde (111 mg, 63%). This intermediate (371 mg, 2 mmol) was dissolved in THF (3 mL) and NaBH4 (38 mg, 5 mmol) was added followed by 3 drops of water. The reaction mixture was agitated for 4 h then added to a saturated solution of NaHCO3 (10 mL). This mixture was stirred for 1 h and the intermediate, (1-ethyl-4-methyl-1H-indol-3-yl)-methanol was isolated by filtration and dried (330 mg, 88% yield). This intermediate was then convened to the title compound using methods similar to those described in Example 31. LCMS (ESMS): m/z 420 (M+H+).

Provenance & Evidence