Tetrahydrofuran → HCID 86656396, compound

Participants

Reaction Steps

To a mixture of N′-hydroxy-2-(trifluoromethyl)-4-vinylbenzimidamide (460 mg, 2 mmol), 3-phenyl-4-(trifluoromethyl)isoxazole-5-carboxylic acid, Int-I (350 mg, 1.361 mmol), and DIEA (0.475 mL, 2.72 mmol) in DMF (10 mL) was added BOP—Cl (346 mg, 1.361 mmol). The reaction mixture was stirred at room temperature for 2 hours and then 1M TBAF in THF (1.361 mL, 1.361 mmol) was added. The reaction was stirred overnight, diluted with ethyl acetate, and washed with H2O. The organic layer was dried with MgSO2, filtered, and concentrated. The resulting solids were purified on a silica gel cartridge using an EtOAc/hexanes gradient to yield 56 mg of 5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-3-(2-(trifluoromethyl)-4-vinylphenyl)-1,2,4-oxadiazole. MS (m+1)=452. HPLC Peak RT=2.03 minutes (Analytical Method B).

Provenance & Evidence