Methyl iodide → HCID 58566577, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (310) (20 mg, 0.05 mmol) in DMF (3 mL) was added sodium hydride (4.3 mg, 2 eq.) and the reaction mixture was stirred at 40° C. for 1 hour. The solution was warmed to room temperature, an excess of methyl iodide was added and the reaction was sealed and warmed to 40° C. overnight. The reaction was quenched with water and extracted with ethyl acetate (2×20 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography to afford compound (311). 1H NMR (400 MHz, CDCl3) δ 6.97 (d, J=8.2 Hz, 1H), 6.93-6.91 (m, 2H), 6.78 (d, J=8.2 Hz, 1H), 4.99 (s, 2H), 3.83 (s, 2H), 3.68 (s, 3H), 2.94-2.90 (m, 2H), 2.56-2.52 (m, 2H), 2.20 (s, 3H), 2.12 (s, 3H), 1.54 (s, 6H). LC-MS ESI m/z: found 384.5 (M−H)−.

Provenance & Evidence