Cesium carbonate → HCID 66740288, compound

Participants

Reaction Steps

To a stirred solution of 5-(2-(4-fluoro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole-2-thiol (548 mg, 1.52 mmol) and 4-(3-(tert-butyldimethylsilyloxy)propoxy)-2-chloro-6-fluorobenzyl methanesulfonate (681 mg, 1.60 mmol) in CH3CN (5 mL) was added Cs2CO3 (743 mg, 2.28 mmol, 1.5 eq). The reaction mixture was stirred for 2 h, filtered and evaporated in vacuo to give a residue, which was purified by flash column chromatography (EtOAc/Hex=1:4) to afford 2-(4-(3-(tert-Butyldimethylsilyloxy)propoxy)-2-chloro-6-fluorobenzylthio)-5-(2-(4-fluoro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole (756 mg, 72%). 1H NMR (400 MHz, CDCl3) δ 7.20 (s, 1H), 6.85 (dd, J=11.04, 8.48 Hz, 1H), 6.80-6.72 (m, 2H), 6.66 (dd, J=2.37, 1.50 Hz, 1H), 6.56 (dd, J=8.11, 2.19 Hz, 1H), 6.48 (ddd, J=8.41, 4.28, 2.19 Hz, 2H), 6.44 (d, J=2.45 Hz, 1H), 6.39-6.32 (m, 2H), 4.19 (d, J=1.41 Hz, 2H), 3.99 (t, J=6.19 Hz, 2H), 3.83-3.72 (m, 5H), 1.95 (dd, J=12.08, 6.05 Hz, 2H), 1.48 (s, 6H), 0.96-0.84 (m, 10H), 0.03 (t, J=4.73 Hz, 6H).

Provenance & Evidence