Toluene → HCID 57941029, compound

Participants

Reaction Conditions

Reaction Steps

Under an argon stream, a mixture of 5-bromo-2-[(E)-2-[4-(trifluoromethyl)phenyl]ethenyl]benzoxazole (Compound of Reference Example 44) (129 mg), phenylboric acid (171 mg), tetrakis(triphenylphosphine)palladium(0) (61 mg), 2 M sodium carbonate (1.05 ml), toluene (3.15 ml) and tetrahydrofuran (1.05 ml) was stirred at 90° C. for 24 hours. The reaction mixture was subjected to distribution into ethyl acetate-tetrahydrofuran (3:1, v/v) and water. The organic layer was washed with water and dried over MgSO4, and the solvent was distilled off under reduced pressure. The residue was subjected silica gel column chromatography and the fraction eluted with ethyl acetate-hexane (1:6, v/v) was concentrated under reduced pressure. The resulting crystals were collected by filtration to obtain 5-phenyl-2-[(E)-2-[4-(trifluoromethyl)phenyl]ethenyl]benzoxazole (70 mg, 55%). The compound was recrystallized from ethyl acetate-hexane.

Provenance & Evidence