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(Reference: Ind. Acad. Sci. 1939, 49, 101-4.) A solution of 1-{5-[4-(3,4-dichloro-phenyl)-1H-imidazol-2-yl]-pyridin-2-yl}-piperazine (155 mg, 0.41 mmol), sodium carbonate (66 mg, 0.62 mmol, 1.5 equiv) and 1-chloro-2-methyl-propan-2-ol (51 μl, 53 mg, 0.50 mmol, 1.2 equiv) in 50% aqueous ethanol (20 ml) under nitrogen atmosphere was heated at reflux overnight. The reaction mixture was then diluted with brine and extracted with ethyl acetate (3×25 ml). The combined organic phases were dried over anhydrous magnesium sulfate, filtered, and -concentrated in vacuo. Purification of the residue by flash column chromatography (50% THF/0.5% ammonium hydroxide/hexanes) provided the desired product (100 mg, 54%).

1. temperatureat reflux overnight
2. extractionextracted with ethyl acetate (3×25 ml)
3. dry with materialThe combined organic phases were dried over anhydrous magnesium sulfate
4. filtrationfiltered
5. customPurification of the residue by flash column chromatography (50% THF/0.5% ammonium hydroxide/hexanes)