Indazolinone → 1-[4-(5-Fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-1,2-dihydroindazol-3-one

Participants

Reaction Steps

To a solution of 2-[2-(5-fluoro-2-methoxyphenyl)-2-methylpropyl]-2-trifluoromethyloxirane (0.29 g) and 1,2-dihydroindazol-3-one (0.17 g) in anhydrous dimethylsulfoxide (1 mL) was added sodium bis(trimethylsilyl)amide (1.0M in tetrahydrofuran, 1.0 mL). After 14 days, the reaction mixture was diluted with ethyl acetate and washed twice with water. The organic phase was dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by preparative TLC (eluted with 1% ethanol-methylene chloride) to give 1-[4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-1,2-dihydroindazol-3-one as a white solid (91 mg), m.p. 141° C.-144° C.

Provenance & Evidence