Benzyl Alcohol → 8-(Benzyloxy)-6-bromo-2,3-dimethylimidazo[1,2-a]pyridine

HRID 1354166Notes

Reaction equation

HRID 1354166 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[Br:11][C:12]1[CH:13]=[C:14](Br)[C:15]2[N:16]([C:18]([CH3:22])=[C:19]([CH3:21])[N:20]=2)[CH:17]=1>CN(C)C=O>[CH2:1]([O:8][C:14]1[C:15]2[N:16]([C:18]([CH3:22])=[C:19]([CH3:21])[N:20]=2)[CH:17]=[C:12]([Br:11])[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 121060806,8-Dibromo-2,3-dimethylimidazo[1,2-a]pyridine

Product 1

HCID 121060818-(Benzyloxy)-6-bromo-2,3-dimethylimidazo[1,2-a]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

With ice-cooling, 34.8 ml of benzyl alcohol are added dropwise to a suspension of 13.5 g of sodium hydride (60% suspension in paraffin) in 510 ml of dimethylformamide, and the mixture is stirred for 1 h until the evolution of gas has ceased. 51.2 g of 6,8-dibromo-2,3-dimethylimidazo[1,2-a]pyridine are then introduced in small portions, and the mixture is stirred at room temperature for 40 h. The mixture is then poured into 1 l of ice-water and extracted three times with in each case 100 ml of dichloromethane, the combined organic extracts are washed with saturated aqueous ammonium chloride solution and twice with water and concentrated to dryness under reduced pressure, and the residue is triturated with a little ethyl acetate. The resulting precipitate is filtered off and dried under reduced pressure. This gives 43.2 g of the title compound of m.p. 151–3° C. (ethyl acetate).

Workup

  1. temperatureWith ice-cooling
  2. stirringthe mixture is stirred at room temperature for 40 h
  3. extractionextracted three times with in each case 100 ml of dichloromethane
  4. washthe combined organic extracts are washed with saturated aqueous ammonium chloride solution and twice with water
  5. concentrationconcentrated to dryness under reduced pressure
  6. customthe residue is triturated with a little ethyl acetate
  7. filtrationThe resulting precipitate is filtered off
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-815b59ccbda54c27b776a95aa884d4d3
Source dataset
uspto-grants-2007_05
Patent number
US07223771B2

Reaction notes

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