2-Methylindole → 1-(4-Methoxyphenyl)-2-methyl-1H-indole

Participants

Reaction Steps

1-(4-Methoxyphenyl)-2-methyl-1H-indole was synthesized according to Buchwald et al. J. Am. Chem. Soc. 2001, 123, 7727. 2-Methylindole (157 mg, 1.2 mmol), 4-iodoanisole (234 mg, 1 mmol), copper(I) iodide (2 mg, 0.01 mmol), trans-1,2-diaminocyclohexane (11.4 mg, 0.1 mmol), and potassium phosphate tribasic (446 mg, 2.1 mmol) were stirred in dioxane (1 mL) at 90° C. overnight. The reaction mixture was filtered through a pad of silica and washed with ethyl acetate. SiO2 chromatography with 5-20% ethyl acetate/hexanes gave 175 mg of the desired product (74% yield). LC-MS (C16H15NO calc'd 237) m/z 238 (M+H).

Provenance & Evidence