3,5-Dimethyl-4-hydroxybenzonitrile → 4-{2-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclopropyl-ethoxy}-3,5-dimethyl-benzonitrile

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Reaction Steps

The title compound was prepared from 2-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclopropyl-ethanol, 3,5-dimethyl-4-hydroxybenzonitrile (commercially available), tri-n-butylposphine and N′N′N′N-tetramethylazodicarboxamide. The compound was purified by silica gel chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of heptane:ethyl acetate (100:0 to 60:40). The so-obtained solid was again chromatographed on a preparative HPLC system using a Phenomenex Gemini column eluting with a gradient of acetonitril and water (containing 5% formic acid). White foam (20%). MS (Turbo Spray): m/z=478.149 [M+H].

Provenance & Evidence