2-Aminopyridine → Imidazo(1,2-a)pyridine, 2-(p-nitrophenyl)-

HRID 339552Notes

Reaction equation

HRID 339552 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][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1)=O.C(=O)(O)[O-].[Na+]>CCO>[N+:18]([C:15]1[CH:16]=[CH:17][C:12]([C:10]2[N:1]=[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][N:3]3[CH:9]=2)=[CH:13][CH:14]=1)([O-:20])=[O:19]

Participants

5

Reactant 3

HCID 104392-AminopyridineHCID 668402-Bromo-4'-nitroacetophenoneHCID 516892Sodium Bicarbonate

Product 1

HCID 201134Imidazo(1,2-a)pyridine, 2-(p-nitrophenyl)-Yield 55.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-aminopyridine (0.20 g, 2.11 mmol) and 2-bromo-4′-nitroacetophenone (0.5 g, 2.05 mmol) in EtOH (25 ml) was heated under reflux for 18 h. The reaction mixture was allowed to cool and sodium bicarbonate (88 mg, 1.05 mmol) was added and heating was continued for 2 h. On cooling to room temperature, the solvent was removed under reduced pressure and the residue was dissolved in DCM (40 ml), washed with water (40 ml), and dried (Na2SO4). The solvent was removed under reduced pressure to give a brown solid which was purified by flash chromatography (15:1 DCM/MeOH) to give the title compound (0.27 g, 54%) as a yellow solid.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 h
  3. temperatureto cool
  4. temperatureheating
  5. customthe solvent was removed under reduced pressure
  6. dissolutionthe residue was dissolved in DCM (40 ml)
  7. washwashed with water (40 ml)
  8. dry with materialdried (Na2SO4)
  9. customThe solvent was removed under reduced pressure
  10. customto give a brown solid which
  11. customwas purified by flash chromatography (15:1 DCM/MeOH)

Sources & evidence

ORD record
ord-faaa44c490204572bf73bc3eab920914
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Reaction notes

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