Methyl iodide → HCID 86673057, compound

Participants

Reaction Steps

A solution of 7-(3-aminophenylethynyl)-2-(Isoquinolin-3-yl)-chromen-4-one O-tert-butyl oxime (tert-butyl protected oxime of example 29) (127 mg, 0.286 mmol) in dimethylformamide (3 ml) was added to a cold suspension of sodium hydride (60% in mineral oil, 24 mg, 0.608 mmol) in DMF (1 ml). The reaction mixture was stirred for 1 hour at room temperature and cooled to 0° C. Iodomethane (43 μl, 0.690 mmol) was added and the solution was stirred at room temperature for 18 hours. The mixture was poured onto water and extracted with ethyl acetate. The organic extracts were washed with water, brine, dried over sodium sulfate and absorbed over silica gel for purification by flash chromatography (gradient cyclohexane/dichloromethane: 0-45%) to yield 2-Isoquinolin-3-yl-7-{3-methylaminophenylethynyl}-chromen-4-one O-tert-butyl oxime (65 mg, 50%) as a beige solid.

Provenance & Evidence