Methyl iodide → HCID 9823708, compound

Participants

Reaction Steps

A mixture of 4-(3-bromo-4,5-dimethoxy-phenyl)-3-cyano-4H-indolo[4,5-b]pyran (51 mg, 0.124 mmol), iodomethane (23 μL, 0.370 mmol) and cesium carbonate (120 mg, 0.368 mmol) in acetone (2 mL) was stirred at room temperature in a sealed tube. After stirring at room temperature for 2.5 days, the reaction was diluted with EtOAc (20 mL). The insoluble material was filtered, and washed with EtOAc (30 mL). The EtOAc solution were combined, washed with brine (2×5 mL), dried over MgSO4, and evaporated to yield an off-white solid. The crude product was purified by column chromatography (silica gel, EtOAc:hexanes, 1:1) to yield 51 mg (97%) of an off-white solid. 1H NMR (CDCl3): 7.43 (d, J=0.6 Hz, 1H), 7.07 (d, J=3.3 Hz, 1H), 7.05 (dd, J=0.6, 8.4 Hz, 1H), 6.95 (d, J=2.1 Hz, 1H), 6.76 (d, J=2.4 Hz, 1H), 6.72 (d, J=8.4 Hz, 1H), 6.58 (dd, J=0.6, 3.3 Hz, 1H), 4.81 (s, 1H), 3.84 (s, 3H), 3.82 (s, 3H), 3.78 (s, 3H).

Provenance & Evidence