Methyl iodide → 3-Methyl-4-methylamino-benzofuran-2-carboxylic acid ethyl ester

Participants

Reaction Steps

To 4-amino-3-methyl-benzofuran-2-carboxylic acid ethyl ester (500 mg, 2.28 mmol, 1 eq.) was added iodomethane (310 uL, 6.16 mmol, 2.7 eq.), sodium carbonate (314 mg, 2.96 mmol, 1.3 eq.), and ethanol (10 mL) and reaction was heated at reflux for 16 hours. 3-Methyl-4-methylamino-benzofuran-2-carboxylic acid ethyl ester was obtained in 17% yield after flash column chromatography, eluting with ethyl acetate/hexanes. (90 mg) 1H NMR (400 MHz, DMSO-d6) δ ppm 1.3 (t, J=7.1 Hz, 3 H) 2.7 (s, 3 H) 4.3 (q, J=7.1 Hz, 2 H) 6.5 (dd, J=7.8, 0.8 Hz, 1 H) 6.8 (d, J=8.3 Hz, 1 H) 7.2 (t, J=8.1 Hz, 1 H).

Provenance & Evidence