Dimethyl Sulfoxide → 2-[2-(Benzyloxy)-1,1-dimethylethyl]-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

Participants

Reaction Conditions

Reaction Steps

Triethylamine (222 μl, 1.59 mmol), (3S)-3-(dimethylamino)pyrrolidine (152 μl, 1.19 mmol) were added to a dimethyl sulfoxide (16.5 ml) solution of 2-[2-(benzyloxy)-1,1-dimethylethyl]-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-66) (330 mg, 0.796 mmol), followed by stirring overnight at 90° C. After cooling, the reaction liquid was diluted with ethyl acetate, washed three times with saturated brine, then dried over anhydrous magnesium sulfate, concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform:methanol=100:1) to obtain the entitled compound (369 mg, 91%) as a pale brown oil.

Provenance & Evidence