Water → 7-(4-Chlorophenyl)-2-(4-(methylsufonyl)benzyl)-8-(pyridin-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3(2h)-one

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To a stirring solution of 7-(4-chlorophenyl)-8-(pyridin-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one (16 mg, 0.05 mmol) in DMF (0.25 mL) at room temperature under argon was added K2CO3 (14 mg, 0.1 mmol), followed by 1-(chloromethyl)-4-(methylsulfonyl)benzene (11 mg, 0.0547 mmol). The reaction mixture was stirred at 70° C. for 10 min. After the reaction mixture was cooled to room temperature, water (2 mL) and EtOAc (5 mL) were added. The layers were separated. The organic layer was dried (MgSO4), filtered, and concentrated under reduced pressure to obtain crude product. This was purified by reverse phase preparative HPLC (without TFA) to isolate 14.5 mg of the title compound as a pale yellow solid. HPLC/MS: retention time=2.27 min, [M+H]+=491.

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