Triethylamine → 7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-5-methyl-6-phenyl-2-[(E)-2-phenylethenyl]-1,3-benzoxazole-4-carbonitrile

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Reaction Conditions

Reaction Steps

7-Fluoro-5-methyl-6-phenyl-2-[(E)-2-phenylethenyl]-1,3-benzoxazole-4-carbonitrile (I-92) (200 mg, 0.56 mmol) was dissolved in dimethylsulfoxide (2 ml), triethylamine (190 μl, 1.35 mmol) and (3S)-3-(dimethylamino)pyrrolidine (86 μl, 0.68 mmol) were added, followed by stirring at 90° C. for 15 hours under nitrogen atmosphere. After cooling to room temperature, ethyl acetate was added, followed by fractionation with water. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate. The solvent was evaporated away and the resulting residue was subjected to silica gel column chromatography, eluted with a mixed solvent of chloroform/methanol (50:1, v/v), recrystallized and purified with n-hexane/ethyl acetate to obtain the entitled compound (163 mg, 65%) as a yellow solid.

Provenance & Evidence