m-Chloroperbenzoic acid → 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-[2-(methylsulfinyl)ethyl]-1-naphthalenecarboxamide

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Reaction Conditions

Reaction Steps

m-Chloroperoxybenzoic acid (47 mg, 70% purity) was added at −78° C. to a stirred solution of 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-[2-(methylthio)ethyl]-1-naphthalenecarboxamide (i.e. the product of Example 1, Step D, 100 mg) in dichloromethane (10 mL). The reaction mixture was stirred at −78 to −70° C. for 2.5 h, then quenched with saturated aqueous sodium bicarbonate and extracted with dichloromethane. The organic extract was washed with brine, dried over sodium sulfate, and concentrated under reduced pressure to provide the title compound (102 mg), a compound of this invention, as a white solid. 1H NMR (CDCl3): δ 8.78 (d, 1H), 8.29 (d, 1H), 7.42-7.64 (m, 7H), 7.37 (br t, 1H), 4.23 (d, 1H), 4.00 (q, 2H), 3.88 (d, 1H), 3.18 (dt, 1H), 2.89 (dt, 1H), 2.62 (s, 3H).

Provenance & Evidence