Bromine → 3-Bromo-8-fluoroimidazo[1,2-a]pyridine
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[Br:1]Br.[K+].[Br-].[F:5][C:6]1[C:7]2[N:8]([CH:12]=[CH:13][N:14]=2)[CH:9]=[CH:10][CH:11]=1.CC([O-])=O.[Na+]>CO.O>[Br:1][C:12]1[N:8]2[CH:9]=[CH:10][CH:11]=[C:6]([F:5])[C:7]2=[N:14][CH:13]=1[Br:1]Br.[K+].[Br-].[F:5][C:6]1[C:7]2[N:8]([CH:12]=[CH:13][N:14]=2)[CH:9]=[CH:10][CH:11]=1.CC([O-])=O.[Na+]>CO.O>[Br:1][C:12]1[N:8]2[CH:9]=[CH:10][CH:11]=[C:6]([F:5])[C:7]2=[N:14][CH:13]=1A solution of bromine in MeOH, saturated with KBr (0.86 M, 1.0 ml, 0.86 mmol) was added to a cooled, stirred solution of 8-fluoroimidazo[1,2-α]pyridine (118 mg, 0.86 mmol) and NaOAc (85 mg, 1.04 mmol) in methanol saturated with KBr (1.6 ml). After 2 min, the solution was poured into water (50 ml) and the resulting yellow solution extracted with CH2Cl2 (3×50 ml). The combined organic fractions were dried over anhydrous Na2SO4 and concentrated in vacuo, yielding 3-bromo-8-fluoroimidazo[1,2-α]pyridine as a yellow solid (155 mg, 83%), used without further purification: δH (400 MHz, CDCl3) 6.86-6.91 (1H, m), 6.95-6.99 (1H, m), 7.65 (1H, s), 7.98 (1H, dd, J 0.8 and 6.7); m/z (ES+) 217 (100%, [MH]+), 215 (100).
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