Tetrabutylammonium Fluoride → HCID 66740014, compound

Participants

Reaction Steps

To a solution of 2-(4-(3-(tert-Butyldimethylsilyloxy)propoxy)-2-chloro-6-fluorobenzylthio)-5-(2-(4-fluoro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole (750 mg, 1.08 mmol) in THF (10 mL) was added dropwise TBAF (1.0M in THF, 0.54 mL, 0.54 mmol). After the reaction was complete, it was quenched by addition of AcOH (0.5 mL). The mixture was evaporated in vacuo and the residue was purified by flash chromatography (EtOAc/Hex=1:2) to give the title compound (592 mg, 95%). 1H NMR (400 MHz, CDCl3) δ 7.29-7.26 (m, 1H), 7.21 (d, J=0.96 Hz, 1H), 6.91-6.84 (m, 1H), 6.76 (dt, J=8.18, 0.81 Hz, 3H), 6.70-6.65 (m, 1H), 6.58 (d, J=8.03 Hz, 1H), 6.52-6.43 (m, 2H), 6.38-6.30 (m, 2H), 4.15 (s, 3H), 4.06 (t, J=5.98 Hz, 3H), 3.84 (t, J=5.89 Hz, 2H), 3.79 (t, J=10.73 Hz, 4H), 2.13-1.97 (m, 4H), 1.48 (s, 8H).

Provenance & Evidence