3-Picoline (I) is oxidized to the corresponding N-oxide (II) by means of peracetic acid. Condensation of (II) with dimethylcarbamoyl chloride furnishes carbamate (III), which is then reacted with cyanotrimethylsilane, producing 2-cyano-5-methylpyridine (IV). Subsequent addition of methylmagnesium iodide to the cyanopyridine (IV) gives rise to the pyridyl ketone (V).
Alkylation of 2-chlorobenzimidazole (VI) with iodomethane and NaOH leads to 2-chloro-1-methylbenzimidazole (VII). The 2-chloro group of (VII) is then displaced with hydrazine hydrate to afford hydrazine (VIII). Finally, condensation between ketone (V) and hydrazine (VIII) gives rise to the target hydrazone.