2-Chloro-4-pyridinecarboxaldehyde → (2-chloropyridin-4-yl)(1-methyl-4-(3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazol-5-yl)-1H-imidazol-2-yl)methanol

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To a solution of 5-(1-methyl-1H-imidazol-4-yl)-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole (500 mg, 1.61 mmol) in THF (10 mL) at −78° C., n-BuLi (2.0 mL, 3.2 mmol, 1.6 M) was added slowly. After stirred at −78° C. for 30 min, 2-chloroisonicotinaldehyde (454 mg, 3.22 mmol) in THF (5 mL) was dropwise added. The mixture was gradually warmed to 0° C., and stirred for 1 h. After quenched by water (20 mL), the mixture was extracted by EA (2×20 mL). The combined organic phases were washed by water (2×30 mL) and brine (30 mL), dried over Na2SO4, filtered, and concentrated to afford the crude product, which was purified by prep-TLC (EtOAc:Petroleum ether=1:1) to give (2-chloropyridin-4-yl)(1-methyl-4-(3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazol-5-yl)-1H-imidazol-2-yl)methanol as a yellow solid (230 mg, 31.7%). MS (ES+) C19H13ClF3N5O3 requires: 451, found: 452 [M+H]+.

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