N-(4-(3-bromophenyl)-3-oxobutan-2-yl)-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole-5-carboxamide → 3-(4-(Trifluoromethoxy)phenyl)-1,2,4-oxadiazole

Participants

Reaction Steps

A solution of N-(4-(3-bromophenyl)-3-oxobutan-2-yl)-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole-5-carboxamide (200 mg, 0.4 mmol) in POCl3 (5 mL) was stirred at 110° C. for 5 h, cooled to RT, concentrated, and neutralized with aqueous K2CO3 (˜8M). The residue was diluted with H2O, and extracted with EtOAc. The combined organic layers were washed with H2O and brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by prep-TLC (Petroleum ether:EtOAc=5:1) to afford 545-(3-bromobenzyl)-4-methyloxazol-2-yl)-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole (100 mg, 52%) as a white solid. MS (ES+) C20H13BrF3N2O2 requires: 479, 481, found: no desired peak; 1H NMR (500 MHz, CDCl3) δ 8.23 (d, J=9.0 Hz, 2H), 7.42-7.31 (m, 4H), 7.23-7.

Provenance & Evidence