HCID 667570, compound → HCID 12044772, compound

Participants

Reaction Conditions

Reaction Steps

4-(4-Fluorophenyl)-5-(4-pyridyl)-1H-imidazole (3) (1 g 4.18 mmol) is dissolved in DMF/THF (50 ml/20 ml) and cooled to −78° C. Potassium bis-(trimethylsilyl)-amide (15% in toluene; 6.7 ml 5 mmol) is introduced at −78° C., stirred for 30 min. then 2-(trimethylsilyl)ethoxymethylchloride is added and the reaction mixture warmed up to r.t., poured on water after 2 hrs. and extracted 3× with ethyl acetate. The combined organic phases are dried over Na2SO4, evaporated to dryness and chromatographed (SiO2 acetone/hexane 4/6 to 6/4) to give 1-(2-(trimethylsilyl)ethoxymethyl)-4-(4-fluorophenyl)-5-(4-pyridyl)imidazole, being eluted first as white crystals (218 mg 14%) followed by 4-(4-pyridyl)-5-(4-fluorophenyl)-1-(2-(trimethylsilyl)ethoxymethyl) imidazole as white crystals (590 mg 38%). The correct assignment of the structures was achieved by ROESY, HSQC and HMBC spectrometry.

Provenance & Evidence