[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]2[N:14]=[C:15]([OH:17])[CH:16]=[C:12]2[C:11]([CH3:18])=[N:10][N:9]=1.[Br:19]Br>C(O)(=O)C.O>[Br:19][C:16]1[C:15]([OH:17])=[N:14][N:13]2[C:12]=1[C:11]([CH3:18])=[N:10][N:9]=[C:8]2[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[F:1]To a stirred solution of 7-(2-fluorophenyl)-2-hydroxy-4-methylpyrazolo[1,5-d][1,2,4]triazine (1.48 g, 6.06 mmol) in glacial acetic acid (20 ml) was added, dropwise, bromine (0.343 ml, 6.66 mmol) and the mixture was stirred at room temperature for 20 min. The mixture was then diluted with water (80 ml) and the resulting solid was collected by filtration, washed with water and dried at 60° C. under vacuum to afford 1.85 g (94%) of the title compound as a cream solid: 1NMR (360 MHz, DMSO-d6) δ 2.88 (3H, s), 7.42-7.47 (2H, m), 7.67-7.76 (2H, m); MS (ES+) m/e 323/325 [M+H]+.
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