Methyl iodide → HCID 23435575, compound

Participants

Reaction Steps

A mixture of 9H-fluoren-9-ylmethyl-6-[5-cyano-1H-pyrrol-2-yl]-2,4,4-trimethyl-2H-3,1-benzoxazine-1(4H)-carboxylate (0.4 g, 0.8 mmol) and potassium carbonate (1.5 g) in anhydrous DMF was treated at ambient temperature under a blanket of nitrogen with iodomethane (1.5 mL, excess). The mixture was stirred for 30 minutes. A saturated ammonium sulfate solution (50 mL) and ethyl acetate (50 mL) was added. The organic layer was separated and aqueous layer was extracted with ethyl acetate (3×15 mL). The combined organic layers were dried (MgSO4), evaporated to yield the title compound as a white solid (0.35 g, 87%): mp 63-64° C.; 1H-NMR (DMSO-d6) δ 7.90 (m, 2H), 7.62 (d, 1H, J=7.7 Hz), 7.58 (d, 1H, J=7.7 Hz), 7.40 (m, 2H), 7.29-7.32 (m, 3H), 7.14 (dd, 1H, J=8.1, 1.9 Hz), 7.01-7.04 (m, 2H), 6.33 (d, 1H,J=4.3 Hz), 5.31 (q, 1H, J=5.8 Hz), 4.88 (dd, 1H, J=10.8, 5.0 Hz), 4.65 (dd, 1H, J=10.8, 4.6 Hz), 4.34 (t, 1H, J=4.6 Hz), 3.71 (s, 3H), 1.52 (s, 3H), 1.21 (s, 3H), 1.06 (d, 3H, J=5.4 Hz); MS (ESI) m/z 504 [M+H]+.

Provenance & Evidence