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

HRID 985103Notes

Reaction equation

HRID 985103 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

34.8 ml of benzyl alcohol are added dropwise with ice cooling to a suspension of 13.5 g of sodium hydride (60% strength suspension in paraffin) in 510 ml of dimethylformamide and the mixture is stirred for 1 h until the evolution of gas is complete. 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. It is then poured onto 1 l of ice water, extracted three times with 100 ml of dichloromethane each time, the combined organic extracts are washed with saturated aqueous ammonium chloride solution and twice with water, concentrated to dryness in vacuo and the residue is stirred with a little ethyl acetate. The precipitate obtained here is filtered off and dried in vacuo. 43.2 g of the title compound of melting point 151-3° C. (ethyl acetate) are obtained.

Workup

  1. stirringthe mixture is stirred at room temperature for 40 h
  2. extractionextracted three times with 100 ml of dichloromethane each time
  3. washthe combined organic extracts are washed with saturated aqueous ammonium chloride solution and twice with water
  4. concentrationconcentrated to dryness in vacuo
  5. stirringthe residue is stirred with a little ethyl acetate
  6. customThe precipitate obtained here
  7. filtrationis filtered off
  8. customdried in vacuo

Sources & evidence

ORD record
ord-16689c0601d5447bb6ef681567a73ce8
Source dataset
uspto-grants-2005_03
Patent number
US06869949B2

Reaction notes

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