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2-Amino-5-methylpyridine → 6-Methyl-2-(4-nitrophenyl)imidazo[1,2-a]pyridine

HRID 339554
Notes
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Reaction equation

HRID 339554 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][C:16]([N+:19]([O-:21])=[O:20])=[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:14]=[CH:15][C:16]([N+:19]([O-:21])=[O:20])=[CH:17][CH:18]=3)[N:1]=2)[CH:4]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 153482-Amino-5-methylpyridineHCID 668402-Bromo-4'-nitroacetophenoneHCID 516892Sodium Bicarbonate

Product 1

HCID 7499176-Methyl-2-(4-nitrophenyl)imidazo[1,2-a]pyridineYield 40.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-amino-5-picoline (0.88 g, 8.19 mmol) and 2-bromo-4′-nitroacetophenone (2.0 g, 8.19 mmol) in EtOH (50 ml) was heated under reflux for 17 h. The reaction mixture was allowed to cool and sodium bicarbonate (840 mg, 9.99 mmol) was added and heating was continued for 18 h. On cooling to room temperature, the solvent was removed under reduced pressure and the residue was purified by flash chromatography (1:1 Hexane/EtOAc) to give the title compound (0.84 g, 40%) as a yellow solid.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 17 h
  3. temperatureto cool
  4. temperatureheating
  5. customthe solvent was removed under reduced pressure
  6. customthe residue was purified by flash chromatography (1:1 Hexane/EtOAc)

Sources & evidence

ORD record
ord-7b3f524f606a4c85802e103451f69231
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08895313B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes