Ethanol → 7-Bromoimidazo(1,2-a)pyridine

HRID 383302Notes

Reaction equation

HRID 383302 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=1.C([O-])(O)=O.[Na+].[CH3:14][CH2:15]O>>[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[CH:14]=[CH:15][N:8]=[C:4]2[CH:3]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 516892Sodium BicarbonateHCID 6932822-Amino-4-bromopyridine

Product 1

HCID 150989037-Bromoimidazo(1,2-a)pyridine

Procedure

4-Bromo-pyridin-2-ylamine (1 eq, 5.78 mmol, 1 g) is added to a solution of chloroacetic aldehyde (5 eq, 28.9 mmol, 5 ml) in EtOH (25 ml). NaHCO3 (2 eq, 11.6 mmol, 971 g) is then added and the reaction mixture is heated at reflux for 17 h. The solvent is then removed in vacuo and the product is purified by flash column chromatography eluting with 9:1 DCM/MeOH to afford 7-bromo-imidazo-[1,2-a]-pyridine as a brown solid; [M+H]+=198

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureat reflux for 17 h
  3. customThe solvent is then removed in vacuo
  4. customthe product is purified by flash column chromatography
  5. washeluting with 9:1 DCM/MeOH

Sources & evidence

ORD record
ord-76c48c9323a0469e8e1dc4bcc989e123
Source dataset
uspto-grants-2013_02
Patent number
US08367662B2

Reaction notes

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