Chloroacetaldehyde → 6-Bromoimidazo[1,2-a]pyridine

HRID 1890691Notes

Reaction equation

HRID 1890691 reaction equation
Cl[CH2:2][CH:3]=O.C([O-])(O)=O.[Na+].[Br:10][C:11]1[CH:12]=[CH:13][C:14]([NH2:17])=[N:15][CH:16]=1>CCO>[Br:10][C:11]1[CH:12]=[CH:13][C:14]2[N:15]([CH:2]=[CH:3][N:17]=2)[CH:16]=1

Participants

5

Reactant 3

HCID 33ChloroacetaldehydeHCID 706222-Amino-5-bromopyridineHCID 516892Sodium Bicarbonate

Product 1

HCID 27955476-Bromoimidazo[1,2-a]pyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In step 13-1, chloracetaldehyde (55% in water, 0.27 mL, 4.5 mmol) and NaHCO3 (143 mg, 1.7 mmol) were added to a solution of 5-bromopyridin-2-amine (173 mg, 1 mmol) in EtOH (7 mL). The mixture was heated to reflux and continued overnight. The reaction mixture was cooled to room temperature and concentrated under vacuum. Dichloromethane was added to extract the residue. The organic layer was washed with water, brine, dried over Na2SO4, filtered, and evaporated to give the crude product. The crude was purified column chromatography (Silica gel, EtOAc/Hexane, gradient) to give 6-bromoimidazo[1,2-a]pyridine (13-1).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. concentrationconcentrated under vacuum
  4. additionDichloromethane was added
  5. extractionto extract the residue
  6. washThe organic layer was washed with water, brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated
  10. customto give the crude product
  11. customThe crude was purified column chromatography (Silica gel, EtOAc/Hexane, gradient)

Sources & evidence

ORD record
ord-443ae3c042744e3eb89913f17a051947
Source dataset
uspto-grants-2013_08
Patent number
US08507488B2

Reaction notes

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