Tetrahydrofuran → HCID 86757472, compound

Participants

Reaction Steps

1.6M n-BuLi in hexane (0.085 ml 0.13 mmol) is added at −40° C. to a solution of 1-(2-(trimethylsilyl)ethoxymethyl)-4-(4-fluorophenyl)-5-(4-pyridyl)imidazole (Example 2; 50 mg 0.13 mmol) in THF (1.4 ml). After 15 min at −40° C. 4-fluorobenzaldehyde (0.018 ml 0.18 mmol) in THF (0.4 ml) is addded to the reaction mixture, which is warmed to r.t. and after 10 min. poured on water and extracted 3× with ethyl acetate. The combined organic phases are dried over Na2SO4, evaporated to dryness and render the desired is-protected title compound (64 mg). In order to remove the SEM protecting group, the latter material is dissolved in THF (2 ml), treated with Bu4NF (4.3 ml; 1M in THF) for 1 h at 60° C., poured on a saturated solution of NaHCO3 and extracted 3× with ethyl acetate. The combined organic phases are dried over Na2SO4, evaporated to dryness and chromatographed (SiO2 toluene/EtOH/NH3conc. 90/10/0.6) to yield the title compound as white crystals (32 mg 67% over 2 steps)

Provenance & Evidence