Tetrabutylammonium Fluoride → 3-chloro-5-fluoro-4-((5-(2-(4-fluoro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-N-(3-hydroxypropyl)benzenesulfonamide

Participants

Reaction Steps

To a solution of N-(3-(tert-butyldimethylsilyloxy)propyl)-3-chloro-5-fluoro-4-((5-(2-(4-fluoro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)benzenesulfonamide (1.08 g, 1.44 mmol) in THF (10 mL) was added TBAF (1.0M in THF, 0.7 mL, 1.39 mmol). After stirring 2 h, the reaction was quenched with AcOH (1 mL) and then evaporated in vacuo. The residue was purified by column chromatography (Hex/EtOAc=1:2) to give 3-chloro-5-fluoro-4-((5-(2-(4-fluoro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-N-(3-hydroxypropyl)benzenesulfonamide (0.91 g, 99%). 1H NMR (400 MHz, CDCl3) δ 7.69 (d, J=1.11 Hz, 1H), 7.43 (dd, J=8.41, 1.71 Hz, 1H), 7.15 (s, 1H), 6.56 (dd, J=8.17, 2.21 Hz, 1H), 6.48 (ddd, J=4.63, 3.53, 1.95 Hz, 3H), 3.93 (d, J=1.24 Hz, 2H), 3.78 (s, 3H), 3.64 (t, J=5.63 Hz, 2H), 3.29-3.19 (m, 2H), 1.77-1.69 (m, 2H), 1.51 (s, 7H), 1.30-1.23 (m, 1H), 5.41-5.23 (m, 1H), 6.87 (ddd, J=10.85, 9.87, 5.32 Hz, 3H).

Provenance & Evidence