Phenacyl bromide → 6-methyl-2-phenylimidazo[1,2-a]pyridine

HRID 339558Notes

Reaction equation

HRID 339558 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1.Br[CH2:10][C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=O.C(=O)(O)[O-].[Na+]>CCO>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]2[N:3]([CH:10]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:1]=2)[CH:4]=1

Participants

5

Reactant 3

HCID 6259Phenacyl bromideHCID 153482-Amino-5-methylpyridineHCID 516892Sodium Bicarbonate

Product 1

HCID 6961766-methyl-2-phenylimidazo[1,2-a]pyridineYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred mixture of 2-amino-5-picoline (0.56 g, 5.22 mmol) and 2-bromoacetophenone (1.0 g, 5.02 mmol) in EtOH (50 ml) was heated under reflux for 2 h. The reaction mixture was left to cool to room temperature and then sodium bicarbonate (0.76 g, 9.04 mmol) was added and the reaction mixture was heated under reflux for 15 h. The solvent was then removed under reduced pressure and the residue was dissolved in EtOAc (70 ml) and washed with water (40 ml). The organic phase was dried (Na2SO4) and the solvent was removed under reduced pressure to give an orange solid. This solid was purified by flash chromatography (1:1 Hexane/EtOAc) to give the title compound (0.753 g, 70%) as a pale orange solid.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 h
  3. waitThe reaction mixture was left
  4. temperaturethe reaction mixture was heated
  5. temperatureunder reflux for 15 h
  6. customThe solvent was then removed under reduced pressure
  7. dissolutionthe residue was dissolved in EtOAc (70 ml)
  8. washwashed with water (40 ml)
  9. dry with materialThe organic phase was dried (Na2SO4)
  10. customthe solvent was removed under reduced pressure
  11. customto give an orange solid
  12. customThis solid was purified by flash chromatography (1:1 Hexane/EtOAc)

Sources & evidence

ORD record
ord-4d1ea299d3b840a29181c991f09830b3
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Reaction notes

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