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

HRID 383297Notes

Reaction equation

HRID 383297 reaction equation
[Cl: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>>[Cl: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 5818662-Amino-4-chloropyridine

Product 1

HCID 196959017-Chloroimidazo(1,2-a)pyridine

Procedure

4-Chloro-pyridin-2-ylamine (1 eq, 38.9 mmol, 5 g) is added to a solution of chloroacetic aldehyde (3 eq, 117 mmol, 15.1 ml) in EtOH (60 ml). NaHCO3 (2 eq, 77.8 mmol, 6.53 g) is added and the reaction mixture is heated at reflux for 17 h. The solvent is removed in vacuo and the product is purified by flash column chromatography eluting with 8:2 DCM/MeOH to afford 7-chloro-imidazo-[1,2-a]-pyridine as a red solid; [M+H]+=153

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureat reflux for 17 h
  3. customThe solvent is removed in vacuo
  4. customthe product is purified by flash column chromatography
  5. washeluting with 8:2 DCM/MeOH

Sources & evidence

ORD record
ord-91c52970c158455e8c1b4073583b7a76
Source dataset
uspto-grants-2013_02
Patent number
US08367662B2

Reaction notes

Loading…