Chloroacetone → 5-Bromo-2-methylimidazo[1,2-a]pyridine

HRID 1639818Notes

Reaction equation

HRID 1639818 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][CH:3]=1.Cl[CH2:10][C:11]([CH3:13])=O>C(O)C>[Br:1][C:2]1[N:7]2[CH:10]=[C:11]([CH3:13])[N:8]=[C:6]2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6571ChloroacetoneHCID 3008092-Amino-6-bromopyridine

Product 1

HCID 126377285-Bromo-2-methylimidazo[1,2-a]pyridineYield 82.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-Bromopyridin-2-amine (25.0 g, 144 mmol) and 1-chloroacetone (20.0 mL, 251 mmol) were dissolved in ethanol (300 mL) and the mixture was heated under reflux for 3 days. The precipitated solid was collected by filtration and dissolved in dichloromethane. The solution was washed with saturated aqueous sodium hydrogen carbonate solution, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (25.0 g, yield 75%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 days
  3. filtrationThe precipitated solid was collected by filtration
  4. dissolutiondissolved in dichloromethane
  5. washThe solution was washed with saturated aqueous sodium hydrogen carbonate solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-8727d3d50b79473fb812ee93b28ad848
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

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