Sodium Methoxide → 5-Methoxy-7-methylimidazo[1,2-a]pyridine

HRID 2085901Notes

Reaction equation

HRID 2085901 reaction equation
Br[C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[CH:5]=[C:4]([CH3:11])[CH:3]=1.[CH3:12][O-:13].[Na+]>CO>[CH3:12][O:13][C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[CH:5]=[C:4]([CH3:11])[CH:3]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 11160141HCID 11160141, compound

Product 1

HCID 112866295-Methoxy-7-methylimidazo[1,2-a]pyridineYield 62%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 5-bromo-7-methylimidazo[1,2-a]pyridine (2 g, 0.01 mol) and sodium methoxide (25%, 10 mL) in methanol (10 mL) is heated under reflux for 48 h. The solvent is removed and the residue diluted with ethyl acetate (200 mL) and water (150 mL). The organic layer is separated and washed with water and brine, and dried over sodium sulfate. Evaporation of the solvent gave 5-methoxy-7-methylimidazo[1,2-a]pyridine (lg, 62%) as a white semi-solid.

Workup

  1. temperatureunder reflux for 48 h
  2. customThe solvent is removed
  3. additionthe residue diluted with ethyl acetate (200 mL) and water (150 mL)
  4. customThe organic layer is separated
  5. washwashed with water and brine
  6. dry with materialdried over sodium sulfate
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-6b6036b112c94411b304731653bb90e0
Source dataset
uspto-grants-2004_04
Patent number
US06723332B2

Reaction notes

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