1,2-Dichloroethane → 2-{[(4-fluorophenyl)methyl]oxy}-N-(3-methyl-4-isoxazolyl)-5-(trifluoromethyl)benzamide

Participants

Reaction Steps

To a solution of 2-{[(4-fluorophenyl)methyl]oxy}-5-(trifluoromethyl)benzoic acid (may be prepared as described in Description 119; 100 mg, 0.32 mmol in N,N-dimethylformamide (4 ml) was added EDC (122 mg, 0.64 mmol), HOBT (63.4 mg, 0.41 mmol), 3-methyl-4-isoxazolamine (86 mg, 0.64 mmol), DIPEA (0.22 ml, 1.27 mmol) and the mixture was stirred at room temperature overnight. The mixture was then heated to 70° C. overnight (NOTE: it would be better to prepare the acid chloride and react this with the amine). The mixture was diluted with water (25 ml) and extracted with ethyl acetate (3×25 ml). The organics were combined, evaporated under reduced pressure on a buchi and the residue was purified using an MDAP to yield the title compound. 33 mg.

Provenance & Evidence