Methyl iodide → 4-[Ethyl-(3,3-dimethyl-7-isopropyl-2,3-dihydro-benzofuran-5-yl)-amino]-benzoic acid ethyl ester

Participants

Reaction Steps

Following general procedure G and using 4-[(3,3-dimethyl-7-isopropyl-2,3-dihydro-benzofuran-5-yl)-amino]-benzoic acid ethyl ester (Compound 17, 0.064 g, 0.19 mmol), potassium carbonate (0.105×2 g, 0.76×2 mmol) and iodomethane (0.24×2 g, 0.76×2 mmol) in 2 mL of anhydrous N,N-dimethylacetamide, the title compound (0.05 g, 75%) was obtained as a pale yellow oil. This reaction was performed in a sealed tube for 96 hours, with addition of a second equivalent of potassium carbonate and iodomethane to the reaction mixture after 48 hours. 1H NMR (300 MHz, CDCl3): δ 7.75 (d, 2H, J=9.0 Hz), 6.74 (d, 1H, J=2.1 Hz), 6.67 (d, 1H, J=2.1 Hz), 6.49 (d, 2H, J=9.0 Hz), 4.23 (q, 2H, J=7.1 Hz), 4.20 (s, 2H), 3.66 (q, 2H, J=7.1 Hz), 3.01 (heptet, 1H J=6.8 Hz), 1.27 (t, 3H, J=7.1 Hz), 1.25 (s, 6H), 1.19-1.13 (m, 9H).

Provenance & Evidence