Methyl iodide → HCID 11998804, compound

Participants

Reaction Steps

To a stirred solution of Example 24 (0.10 g, 0.25 mmol) in DMF (5 mL) at 0° C. was added sodium hydride (0.01 g, 40% dispersion in oil, 0.28 mmol). After stirring at this temperature for 10 minutes, methyl iodide (0.02 mL, 0.28 mmol) was added. The reaction was stirred at r.t. for 1 h and then quenched by the addition of ice. The reaction mixture was then partitioned between EtOAc (15 mL) and water (10 mL) and the organic phase was dried over MgSO4 and concentrated in vacuo. Purification by column chromatography (SiO2, 1:1 EtOAc/hexanes) gave the title compound (0.08 g, 79%) as a white solid. δH (CDCl3) 7.79 (1H, d, J 7.7 Hz), 7.09-7.24 (3H, m), 6.90 (1H, s), 4.05 (2H, m), 3.82 (1H, d, J 12.0 Hz), 3.79 (1H, bs), 3.68 (3H, s), 3.57 (2H, m), 3.41 (2H, m), 2.95 (1H, m), 2.67 (2H, s), 2.34 (2H, s), 1.11 (6H, s). LCMS (ES+) 410.0 (M+H)+.

Provenance & Evidence