Sodium hydride → Ethyl 3-[4-(2-aminothiazol-5-yl)oxyphenyl]isoxazole-5-carboxylate

Participants

Reaction Steps

To a stirred solution of ethyl 3-(4-hydroxyphenyl)isoxazole-5-carboxylate (0.97 g, 4.16 mmol) in dry THF, sodium hydride (60%, 0.25 g, 6.09 mmol) was added at room temperature and stirred for 10 min. 5-bromothiazol-2-amine (0.5 g, 2.77 mmol) dissolved in 10 mL dry THF was added and continued to stir for additional 1 hr. Reaction mixture was poured on ice cold water and extracted with ethyl acetate (50 mL×3). The combined organic layer was washed with water, brine and dried over sodium sulfate, filtered and concentrated under reduced pressure to get crude material which was purified by silica gel column chromatography using 40-50% ethyl acetate in hexane to provide the title compound (0.19 g).

Provenance & Evidence