Dimethyl Sulfoxide → N-(4-{[tert-butyl(dimethyl)silyl]oxy}butyl)-N-[3-cyano-5-cyclopropyl-2-(4-fluorophenyl)-1-benzo furan-6-yl]methanesulfonamide

Participants

Reaction Steps

A mixture of Example 11A (0.1302 g, 0.352 mmol) and potassium carbonate (0.058 g, 0.422 mmol) in acetonitrile (2 mL) was heated at reflux for 30 minutes, then (4-iodobutoxy)-tert-butyldimethylsilane (0.122 g, 0.387 mmol) was added and the resultant mixture was stirred at reflux for 0.5 hour. The reaction mixture became thick so additional acetonitrile (2 mL) and dimethyl sulfoxide (2 mL) were added, and the resultant mixture was stirred at room temperature for 16 hours. The reaction mixture was concentrated in vacuo to a yellow oil that was taken up in ethyl acetate (100 mL) and washed with 1 N aqueous H3PO4, 10% aqueous NaHCO3, and 10% aqueous NaCl. The organic phase was dried over anhydrous Na2SO4, filtered, and concentrated in vacuo leaving a yellow oil. Purification on a silica gel column (12 g) eluting with a gradient of 10/90 ethyl acetate/hexane to 50/50 ethyl acetate/hexane over 20 minutes afforded the title compound (0.135 g, 69%).

Provenance & Evidence