Sodium hydride → N-(4-Fluoro-phenyl)-N-isobutyl-4-(1-methanesulfonyl-piperidin-4-yloxy)-benzenesulfonamide

Participants

Reaction Steps

To a solution of 1-methanesulfonyl-piperidin-4-ol (61 mg) in anhydrous tetrohydrofuran (5 mL) at room temperature was added NaH (60% dispersion in mineral oil, 15 mg, 369 μmol) and the reaction was stirred at room temperature for 30 minutes. 4-Fluoro-N-(4-fluoro-phenyl)-N-isobutyl-benzenesulfonamide (100 mg, 308 μmol) was added and the reaction was heated at 90° C. for 3 hours. The reaction was allowed to cool to room temperature, water was added and then extracted with EtOAc, concentrated, purified by preparative reverse-phase HPLC and then freeze dried to give the title compound (51.8 mg). 1H NMR (400 MHz, DMSO): δ 7.44 (d, J=8.8 Hz, 2H), 7.13-7.14 (m, 7H), 4.69 (t, J=3.8 Hz, 1H), 3.35 (d, J=10.8 Hz, 4H), 3.28 (d, J=7.4 Hz, 3H), 3.12-3.14 (m, 2H), 2.91 (s, 3H), 2.03 (br s, 3H), 1.71-1.79 (m, 3H), 1.41 (t, J=6.8 Hz, 1H), 0.84 (d, J=6.6 Hz, 6H). LCMS (m/z, Method B) ES+ 484.9 [M+1]+.

Provenance & Evidence