2-Pyridinamine, 5-iodo- → 2-Ethyl-6-iodo-3-methylimidazo[1,2-a]pyridine

HRID 2202965Notes

Reaction equation

HRID 2202965 reaction equation
Br[CH:2]([C:4](=O)[CH2:5][CH3:6])[CH3:3].[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([I:15])=[CH:11][N:10]=1>CCO>[CH2:5]([C:4]1[N:8]=[C:9]2[CH:14]=[CH:13][C:12]([I:15])=[CH:11][N:10]2[C:2]=1[CH3:3])[CH3:6]

Participants

4

Reactant 2

HCID 885792-Pyridinamine, 5-iodo-HCID 5450922-Bromo-3-pentanone

Product 1

HCID 231582522-Ethyl-6-iodo-3-methylimidazo[1,2-a]pyridineYield 30.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred mixture of 2-bromopentan-3-one (2.0 g), 2-amino-5-iodopyridine (1.0 g) and EtOH (50 ml) was heated at reflux for 16 h. The reaction mixture was cooled and concentrated in vacuo. The residue was diluted with water (100 ml), and extracted with DCM. The DCM layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane/EtOAc) to give the title compound (400 mg) as a yellow solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 h
  3. temperatureThe reaction mixture was cooled
  4. concentrationconcentrated in vacuo
  5. additionThe residue was diluted with water (100 ml)
  6. extractionextracted with DCM
  7. washThe DCM layer was washed with brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by silica gel column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-b3768ba3442b4f679e7065f6d0567b05
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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