[NH:1]1[CH:5]=[N:4][C:3]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=2)=[N:2]1.C(=O)([O-])[O-].[K+].[K+].F[C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[C:22]#[N:23]>CN(C=O)C>[N:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[C:3]1[N:4]=[CH:5][N:1]([C:19]2[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=2)[C:22]#[N:23])[N:2]=12-(1H-1,2,4-Triazol-3-yl)pyridine (0.24 g, 1.6 mmol), potassium carbonate (0.45 g, 3.2 mmol) and 3-fluorobenzonitrile (0.20 g, 1.6 mmol) were stirred in DMF (20 mL) at ambient temperature. The resulting reaction mixture was heated at 145° C. for 16 h, after which time it was quenched with H2O (30 mL) and diluted with EtOAc (200 mL). The EtOAc solution was washed with H2O (3×100 mL), then brine (100 mL) and dried (MgSO4), filtered, and concentrated in vacuo. The resulting residue was chromatographed on silica gel eluting with hexane:EtOAc (40:60) to afford 3-(3-pyridin-2-yl-1H-1,2,4-triazol-1-yl)benzonitrile as a white solid.
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