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

HRID 857815Notes

Reaction equation

HRID 857815 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.Br[CH2:9][C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=O>C(O)C>[C:12]1([C:10]2[N:1]=[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][N:3]3[CH:9]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 104392-Aminopyridine

Product 1

HCID 2011362-phenylimidazo[1,2-a]pyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Phenylimidazo[1,2-a]pyridine was prepared by the following procedure. A solution of 2-aminopyridine (9.4 g, 0.1 mol) and bromoacetophenone (19.9 g, 0.1 mol) in ethanol (75 mL) was heated to reflux for 2 h. The ethanol was removed in vacuo and the residue redissolved in 100 mL ethyl acetate. The solution was washed with 1N NaHCO3 (50 mL), followed by a water wash. The organics were dried over magnesium sulfate, filtered and the solvent removed in vacuo. Chromatography on silica with dichloromethane/ethyl acetate (90/10) eluent yielded the 2-phenylimidazo[1,2-a]pyridine in 88% yield, mp 134° C. 1H NMR and mass spectra analysis confirmed the structure.

Workup

  1. custom2-Phenylimidazo[1,2-a]pyridine was prepared by the following procedure
  2. temperatureto reflux for 2 h
  3. customThe ethanol was removed in vacuo
  4. dissolutionthe residue redissolved in 100 mL ethyl acetate
  5. washThe solution was washed with 1N NaHCO3 (50 mL)
  6. washwash
  7. dry with materialThe organics were dried over magnesium sulfate
  8. filtrationfiltered
  9. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-4679d25b5731460c889baaba6ad063b9
Source dataset
uspto-grants-2006_12
Patent number
US07147937B2

Reaction notes

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