Sodium hydride → tert-Butyl 4-{3-ethyl-1-[4-(methylthio)benzyl]-1H-pyrazol-4-yl}-piperidine-1-carboxylate

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Reaction Steps

A solution of 3-ethyl-4-(N-t-butoxycarbonylpiperid-4-yl)-1H-pyrazole (0.83 g, 2.97 mmol, from Step B) in 4 mL DMF was cooled to 0° C. and sodium hydride (155 mg, 3.87 mmol, 60% dispersion in mineral oil) was added cautiously. The mixture was warmed to rt and 4-(ethylthio)benzyl chloride (crude material from Step C) in 6 mL DMF was added. The mixture was stirred for 14 h. The mixture was concentrated and the residue was taken up in methylene chloride. The solution was washed with water and sat'd sodium chloride then dried over magnesium sulfate and concentrated. Flash chromatography (40 g silica, 4/1 hexane/EtOAc) afforded the product.

Provenance & Evidence