Bromine → 3-Bromo-7-methoxyimidazo[1,2-a]pyridine

HRID 985530Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]2[CH:9]=[CH:10][N:11]=[C:5]2[CH:4]=1.C([O-])(=O)C.[Na+].[Br:17]Br.C(=O)([O-])O.[Na+]>[Br-].[K+].CO>[Br:17][C:9]1[N:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][C:5]2=[N:11][CH:10]=1

Participants

Conditions

Temperature: 0 °C

Procedure

7-Methoxyimidazo[1,2-α]pyridine (1.0 g, 6.8 mmol) and sodium acetate (0.67 g, 8.1 mmol) were dissolved in a saturated solution of potassium bromide in methanol (5 ml) and cooled to 0° C. before adding bromine (1.13 g, 7.1 mmol) dropwise over 5 min. The mixture was allowed to stir for 15 min before pouring onto saturated sodium hydrogencarbonate solution (50 ml). The resulting yellow solid was collected by filtration and dried. This solid was purified by flash column chromatography on silica eluting with 50% ethyl acetate in isohexane to afford 3-bromo-7-methoxyimidazo[1,2-α]pyridine (0.4 g, 26%) as a white solid. 1H NMR (360 MHz, CDCl3) δH 3.87 (3H, s), 6.64 (1H, dd, J 2 and 7), 6.88 (1H, d, J 2), 7.45 (1H, s), 7.92 (1H, d, J 7).

Workup

filtrationThe resulting yellow solid was collected by filtration
customdried
customThis solid was purified by flash column chromatography on silica eluting with 50% ethyl acetate in isohexane

Sources & evidence

ORD record: ord-ab94b565ec104a97b57a7fe7acc65077
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06872731B2

Reaction notes

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