[Br:1]Br.[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[N:14][N:13]3[CH:16]=[CH:17][N:18]=[C:12]3[CH:11]=2)=[CH:6][CH:5]=1.C([O-])(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(O)(=O)C.C(OCC)(=O)C>[Br:1][C:16]1[N:13]2[N:14]=[CH:15][C:10]([C:7]3[CH:6]=[CH:5][C:4]([F:3])=[CH:9][CH:8]=3)=[CH:11][C:12]2=[N:18][CH:17]=1
Bromine (0.12 mL, 2.34 mmol) was added dropwise to a stirred mixture of 7-(4-fluorophenyl)imidazo[1,2-b]pyridazine (500 mg, 2.34 mmol) and sodium acetate (289 mg, 3.52 mmol) in Acetic Acid (12 mL) and the mixture was stirred at room temperature for 1 h. The mixture was poured into ethyl acetate and aqueous sodium hydrogen carbonate (50 mL) and extracted with ethyl acetate (3×50 mL). The combined organics were washed with water, dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography to afford the title compound as a white solid. 1H NMR (500 MHz, CD3SOCD3) δ 9.10 (d, 1H); 8.49 (d, 1H); 7.98 (dd, 2H); 7.96 (s, 1H); 7.38 (t, 2H). LRMS (APCI) calc'd for (C12H8BrFN3) [M+H]+, 292.0. found 292.0.
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