Alkylation of 3,5-difluorophenylacetonitrile (I) with bis-(2-chloroethyl)ether (II) affords the tetrahydropyran derivative (III). Subsequent displacement of one fluoride group of (III) with sodium methylsulfide in hot DMF yields thioether (IV). Oxidation of (IV) employing NaIO4 leads to sulfoxide (V). Then, Pummerer rearrangement of sulfoxide (V) with trifluoroacetic anhydride, followed by basic hydrolysis, furnishes thiol (VI)
Arylation of 2-methylimidazole (VII) with1-fluoro-4-iodobenzene (VIII) gives the iodophenyl imidazole (IX). Then, condensation of aryl iodide (IX) with thiophenol (VI) produces the diaryl sulfide (X). Finally, partial hydrolysis of the cyano group of (X) employing KOH in t-butanol yields the target carboxamide