[NH:1]1[CH:5]=[CH:4][N:3]=[N:2]1.[H-].[Na+].F[C:9]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:10]=1[C:11]#[N:12]>C1COCC1.CN(C=O)C>[F:17][C:15]1[CH:16]=[CH:9][C:10]([C:11]#[N:12])=[C:13]([N:2]2[N:3]=[CH:4][CH:5]=[N:1]2)[CH:14]=1To a solution of 1H-1,2,3-triazole (3.5 g, 50.7 mmol) in THF (10 mL) and DMF (20 mL) was added portionwise, NaH (1.3 g, 51 mmol, 95%). The mixture was stirred at room temp for 30 min. Added to this was 2,4-difluorobenzonitrile (7.6 g, 55 mmol) and the mixture was stirred at 85° C. for 3 h. The white mixture was concentrated and purified by flash chromatography eluting with 0%-5%-10% EtOAc/hexane to give the title compound as white needles (0.34 g, 3% yield). 1H-NMR (300 MHz, CDCl3) δ: 7.92 (2H, s), 7.88-7.79 (2H, m), 7.19-7.12 (1H, m). LCMS [M+H]+ calcd for C9H6N4F: 189.05; found: 189.12.
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