[CH3:1][C:2]1[NH:6][N:5]=[C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:3]=1.[Cl:12][C:13]1[CH:18]=[C:17]([CH2:19]Cl)[CH:16]=[CH:15][N:14]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[Cl:12][C:13]1[CH:18]=[C:17]([CH2:19][N:6]2[C:2]([CH3:1])=[N:3][C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[N:5]2)[CH:16]=[CH:15][N:14]=1To a solution of ethyl 5-methyl-1H-1,2,4-triazole-3-carboxylate (50 mg, 0.28 mmol) and 2-chloro-4-(chloromethyl)pyridine (50 mg, 0.31 mmol) in DMF (2 mL), K2CO3 (116 mg, 0.84 mmol) was added. The mixture was stirred at RT overnight, and was then diluted with H2O (20 mL), extracted with EtOAc (3×20 mL), 4:1 CHCl3:iPrOH (3×20 mL), dried with MgSO4 and concentrated under reduced pressure. The crude product was purified on a Biotage pre-packed silica gel column (EtOAc:Hexane 12% to 100% EtOAc) to afford ethyl 1-((2-chloropyridin-4-yl)methyl)-5-methyl-1H-1,2,4-triazole-3-carboxylate (29 mg, 40%) as a white solid. MS (ES+) C12H13ClN4O2 requires: 280 found: 281[M+H]+.
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