Bromine → 2-(3-Bromo-8-fluoroimidazo[1,2-a]pyridin-7-yl)propan-2-ol

HRID 1765097Notes

Reaction equation

HRID 1765097 reaction equation
[F:1][C:2]1[C:3]2[N:4]([CH:12]=[CH:13][N:14]=2)[CH:5]=[CH:6][C:7]=1[C:8]([OH:11])([CH3:10])[CH3:9].[Br:15]Br.[Br-].[K+].C([O-])(=O)C.[Na+]>CO>[Br:15][C:12]1[N:4]2[CH:5]=[CH:6][C:7]([C:8]([OH:11])([CH3:10])[CH3:9])=[C:2]([F:1])[C:3]2=[N:14][CH:13]=1

Participants

6

Reactant 4

HCID 24408BromineHCID 253877Potassium BromideHCID 517045Sodium AcetateHCID 444087292-(8-Fluoroimidazo[1,2-a]pyridin-7-yl)propan-2-ol

Product 1

HCID 674869102-(3-Bromo-8-fluoroimidazo[1,2-a]pyridin-7-yl)propan-2-olYield 45%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(8-Fluoroimidazo[1,2-α]pyridin-7-yl)propan-2-ol (1.00 g, 5.2 mmol) was brominated by treatment with bromine in methanol, in the presence of potassium bromide and sodium acetate, affording 2-(3-bromo-8-fluoroimidazo[1,2-α]pyridin-7-yl)propan-2-ol (637 mg, 45%): δH (360 MHz, CDCl3) 1.72 (6H, s), 7.32 (1H, t, J 6.9), 7.59 (1H, s), 7.89 (1H, d, J 7.3); m/z (ES+) 275 (100%, [M]+), 273 (100).

Sources & evidence

ORD record
ord-f32dc1353d524965b024289d1052a99a
Source dataset
uspto-grants-2007_06
Patent number
US07226926B2

Reaction notes

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