Methyl iodide → HCID 71542818, compound

Participants

Reaction Steps

To a stirred solution of (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-((4-nitrophenoxy)carbonyloxy)ethyl)pyridine 1-oxide (for reference procedure see Example 3, Step 1) (300 mg, 0.513 mmol) in dry THF (5 ml), (3,4-dimethoxyphenyl)methanamine (0.077 ml, 0.513 mmol) was added. The mixture was stirred at RT for 2 hours and then cooled to 0° C. NaH (60% w/w dispersion in mineral oil, 61.5 mg, 1.538 mmol) was added portion wise followed by iodomethane (0.080 ml, 1.281 mmol). The cold bath was removed and the reaction was stirred at RT for 5 hours. The mixture was cooled to 0° C., quenched with water and then extracted with EtOAc. The combined organic layers were dried over Na2SO4, the solvent was evaporated, and the crude was purified by flash chromatography on silica gel column (DCM/MeOH 100/2). The desired product was obtained as a white solid (96 mg, 0.153 mmol, 29.9% yield, MS/ESI+ 626.89 [MH]+[αD]=−12.01, c=0.616, DCM).

Provenance & Evidence