Ethyl Acetate → {3,5-Dimethyl-1-[4-(4-trifluoromethyl-phenylsulfanylmethyl)-benzyl]-1H-pyrazol-4-yl}-acetic acid methyl ester

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Reaction Steps

4-(Trifluoromethyl)thiophenol (0.25 ml, 1.8 mmol) was dissolved in 5 ml dimethylformamide, and K2CO3 (337 mg, 2.4 mmol) was added to the solution. A solution of [1-(4-chloromethyl-benzyl)-3,5-dimethyl-1H-pyrazol-4-yl]-acetic acid methyl ester (intermediate 16.1.2, 1 g, 1.6 mmol) in dimethylformamide was added to the mixture within 5 min, and the mixture was stirred for 1 h at room temperature. Ethyl acetate and water were added, the mixture was washed with aqueous NaOH solution (1 M) and with water. The organic layer was dried over MgSO4 and the solvent was evaporated under reduced pressure. The residue was purified by MPLC (silica gel, CH2Cl2/methanol 99:1) and preparative reversed phase HPLC (gradient of methanol in water+0.1% NH3).

Provenance & Evidence