Methyl iodide → HCID 76462376, compound

Participants

Reaction Steps

To a solution of 1-(2-(4-(2-thiophenylsulfonyl)-1-piperazinyl)-5-(2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl)phenyl)-1-pentyn-3-ol (186 mg, 0.33 mmol, Example 154) in dry THF (5 mL) at room temperature was added sodium hydride (60% dispersion in mineral oil, 134 mg, 3.34 mmol). The reaction mixture was stirred at room temperature for 10 min then methyl iodide (0.21 mL, 3.34 mmol) was added. After stirring for an additional 2 h, the solvent was removed under reduced pressure. The crude material was absorbed onto a plug of silica gel and purified by column chromatography (12 g of silica gel, 10 to 30% ethyl acetate in hexanes), to provide 1,1,1,3,3,3-hexafluoro-2-(3-(3-methoxy-1-pentyn-1-yl)-4-(4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-2-propanol (156 mg) as an off-white solid.

Provenance & Evidence