Sodium Iodide → 5-(1-((2-Chlorothiazol-5-yl)methyl)-5-methyl-1H-1,2,4-triazol-3-yl)-3-(4-(trifluoro methoxy)phenyl)-1,2,4-oxadiazole

Participants

Reaction Steps

To a suspension of 5-(5-methyl-1H-1,2,4-triazol-3-yl)-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole (31 mg, 0.1 mmol) in THF (1 mL), K2CO3 (28 mg, 0.2 mmol), NaI (22 mg, 0.15 mmol), and 5-(chloromethyl)-2-chlorothiazole (25 mg, 0.15 mmol) were added at RT. The mixture was stirred at RT for 3 days. The resulting crude product was filtered and purified by a silica gel column with (EtOAc/Hexane 16% to 100% EtOAc) to give 5-(1-((2-chlorothiazol-5-yl)methyl)-5-methyl-1H-1,2,4-triazol-3-yl)-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole as a white solid (24 mg, 55%). MS (ES+) C16H10F3N6ClO2S requires: 442, 444. found: 443, 445 [M+H]+; 1H NMR (600 MHz, CDCl3) δ 8.28 (d, J=8.9 Hz, 2H), 7.60 (s, 1H), 7.35 (d, J=8.2 Hz, 2H), 5.57 (s, 2H), 2.65 (s, 3H).

Provenance & Evidence