Tetrabutylammonium Fluoride → 2-(4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluorophenoxy)ethanol

Participants

Reaction Steps

To a solution of 2-(4-(2-(tert-butyldimethylsilyloxy)ethoxy)-2,6-difluorobenzylthio)-5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole (440 mg, 0.65 mmol, 1.0 eq) in anhyd DCM was added tetrabutylammonium fluoride (2.9 mL, 2.9 mmol, 4.4 eq, 1.0 M in THF). After stirring 16 h, the reaction was quenched with satd NaHCO3 and extracted with DCM. The combined extracts were washed with water and brine, dried, concentrated and purified (silica, 0 to 80% EtOAc/Hex) to yield 2-(4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluorophenoxy)ethanol (290 mg, 79%) as a white foam: 1H NMR (400 MHz, CDCl3) δ 7.18 (d, J=7.8 Hz, 1H), 7.06 (d, J=8.2 Hz, 1H), 6.74-6.63 (m, 2H), 6.46-6.33 (m, 2H), 6.33-6.20 (m, 4H), 4.03 (s, H), 3.90 (dt, J=8.7, 4.1 Hz, 4H), 3.68 (s, 3H), 1.39 (s, 6H).

Provenance & Evidence