Methyl iodide → HCID 67419119, compound

Participants

Reaction Steps

To a solution of compound 2g (120 mg, 0.28 mmol) in DMF (15 mL) at 10° C., NaH (60% in mineral oil; 13 mg, 0.33 mmol) was added in portions. The mixture was stirred for an additional 45 min and then MeI (116 mg, 0.82 mmol) was added dropwise. The resulting mixture was stirred at 10° C. for 30 min and warmed to rt overnight. The reaction was quenched with water (30 mL) and extracted with EA (40 mL). The organic layer was washed with brine (2×20 mL) and dried over anhydrous Na2SO4. Concentration in vacuo and purification by prep-TLC (PE:EA=1:1) gave compound 2h as a white solid (110 mg, 89% yield). 1H-NMR (400 MHz, CD3OD) δ 7.82 (dd, 1H, J=8.0, 1.6 Hz), 7.51 (t, J=8.8 Hz, 1H), 7.36-7.23 (m, 4H), 7.05-6.99 (m, 5H), 6.72-6.70 (m, 2H), 5.41 (d, J=18.8 Hz, 1H), 4.55 (d, J=19.2 Hz, 1H), 4.10 (m, 1H), 3.82 (s, 3H), 3.28 (dd, J=14.4, 11.6 Hz, 1H), 2.98 (dd, J=15.2, 4.8 Hz, 1H), 2.86 (s, 3H), 2.61 (dd, J=12.8, 9.6 Hz, 1H), 2.47 (dd, J=12.8, 4.8 Hz, 1H). MS (ESI+) m/z: 451 [M+H]+

Provenance & Evidence