Cesium carbonate → Ethyl 2-(diphenylmethyleneamino)-4-(3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)butanoate

Participants

Reaction Conditions

Reaction Steps

A mixture of ethyl 2-(diphenylmethyleneamino)acetate (236 mg, 0.882 mmol), Cs2CO3 (144 mg, 0.441 mmol), 3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-7-vinyl-4,5-dihydronaphtho[1,2-c]isoxazole (Preparation 6A, 100 mg, 0.245 mmol), and anhydrous DMSO (0.6 mL) was purged with nitrogen for 5 min. and then sealed in a 1 dram vial. The mixture was stirred at 50° C. for 2 h. The mixture was cooled, diluted with water (15 mL) and extracted with ethyl acetate (3×5 mL). The combined ethyl acetate extracts were dried (sodium sulfate) and concentrated under reduced pressure. Flash chromatography purification (12 g silica gel column, 10→100% ethyl acetate in hexanes) afforded ethyl 2-(diphenylmethyleneamino)-4-(3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)butanoate (140 mg, 0.207 mmol, 85% yield) as a sticky liquid. The compound had an LC/MS M+1=676.2.

Provenance & Evidence