Chloroacetaldehyde → 8-Bromo-6-methylimidazo[1,2-a]pyridine

HRID 910113Notes

Reaction equation

HRID 910113 reaction equation
Cl[CH2:2][CH:3]=O.[NH2:5][C:6]1[C:11]([Br:12])=[CH:10][C:9]([CH3:13])=[CH:8][N:7]=1>C(#N)C>[CH3:13][C:9]1[CH:10]=[C:11]([Br:12])[C:6]2[N:7]([CH:2]=[CH:3][N:5]=2)[CH:8]=1

Participants

4

Reactant 2

HCID 33ChloroacetaldehydeHCID 5193802-Amino-3-bromo-5-methylpyridine

Product 1

HCID 150988968-Bromo-6-methylimidazo[1,2-a]pyridine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Add chloroacetaldehyde (2.51 g, 32.08 mmol) to a solution of 2-amino-3-bromo-5-methylpyridine (2.0 g, 10.69 mmol) in acetonitrile (200 ml). Reflux the reaction for 4 hours and then cool. Filter the reaction mixture and partition the white solid between saturated aqueous sodium bicarbonate (300 ml) and ethyl acetate. Separate the organic layer, wash with saturated aqueous sodium bicarbonate, dry over magnesium sulfate, and concentrated under reduced pressure to give the title compound as a tan solid.

Workup

  1. temperatureReflux
  2. customthe reaction for 4 hours
  3. temperaturecool
  4. filtrationFilter the reaction mixture
  5. custompartition the white solid between saturated aqueous sodium bicarbonate (300 ml) and ethyl acetate
  6. customSeparate the organic layer
  7. washwash with saturated aqueous sodium bicarbonate
  8. dry with materialdry over magnesium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ea534bbdbc7d4b6fb4570e1d657a7785
Source dataset
uspto-grants-2011_09
Patent number
US08022065B2

Reaction notes

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