The reaction of 3,5-dihydroxybenzoic acid (I) with N,O-dimethylhydroxylamine (II) by means of EDC and NMM in dichloromethane gives the N,O-dimethylbenzamide (III), which is alkylated with butyl bromide (IV) and K2CO3 in hot DMF to yield the dibutoxybenzamide (V). The condensation of (V) with 4-methylpyridine (VI) by means of LDA in THF affords 1-(2,4-dibutoxyphenyl)-2-(4-pyridyl)ethanone (VII), which is oxidized with SeO2 in hot acetic acid to provide the dione (VIII). Finally, this compound is cyclized with 4-chlorobenzaldehyde (IX) and ammonium acetate in refluxing acetic acid to furnish the target imidazole.

The reaction of 3,5-dihydroxybenzoic acid (I) with N,O-dimethylhydroxylamine (II) by means of EDC and NMM in dichloromethane gives the N,O-dimethylbenzamide (III), which is alkylated with butyl bromide (IV) and K2CO3 in hot DMF to yield the dibutoxybenzamide (V). The condensation of (V) with 4-methylpyridine (VI) by means of LDA in THF affords 1-(2,4-dibutoxyphenyl)-2-(4-pyridyl)ethanone (VII), which is oxidized with SeO2 in hot acetic acid to provide the dione (VIII). Finally, this compound is cyclized with 4-chlorobenzaldehyde (IX) and ammonium acetate in refluxing acetic acid to furnish the target imidazole.

The reaction of 3,5-dihydroxybenzoic acid (I) with N,O-dimethylhydroxylamine (II) by means of EDC and NMM in dichloromethane gives the N,O-dimethylbenzamide (III), which is alkylated with butyl bromide (IV) and K2CO3 in hot DMF to yield the dibutoxybenzamide (V). The condensation of (V) with 4-methylpyridine (VI) by means of LDA in THF affords 1-(2,4-dibutoxyphenyl)-2-(4-pyridyl)ethanone (VII), which is oxidized with SeO2 in hot acetic acid to provide the dione (VIII). Finally, this compound is cyclized with 4-chlorobenzaldehyde (IX) and ammonium acetate in refluxing acetic acid to furnish the target imidazole.