[Cl:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1/[CH:4]=[N:5]/[NH:6][C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[C:9]([CH3:14])[N:8]=1.O.O.O.NCl.O>CCO>[Cl:13][C:11]1[CH:10]=[C:9]([CH3:14])[N:8]2[C:4]([C:3]3[CH:15]=[CH:16][CH:17]=[CH:18][C:2]=3[Cl:1])=[N:5][N:6]=[C:7]2[CH:12]=1A mixture of (E)-1-(2-chlorobenzylidene)-2-(4-chloro-6-methylpyridin-2-yl)hydrazine (0.247 g, 0.882 mmol) and chloramine trihydrate (0.273 g, 0.970 mmol) in 7 mL of EtOH was heated at 80° C. for 2 h. After cooling to RT, water was added and the mixture was extracted with EtOAc (3×). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated to give 1.05 g of crude material. The crude material was purified by silica gel chromatography (50-75% EtOAc in hexanes) to afford 7-chloro-3-(2-chlorophenyl)-5-methyl-[1,2,4]triazolo[4,3-a]pyridine as an off white solid. MS (ESI, pos. ion) m/z: 278.0 (M+1).
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