Sodium Methoxide → HCID 119086487, compound

HRID 2202881Notes

Reaction equation

HRID 2202881 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]2[CH:10]=[CH:9][C:8]([I:11])=[CH:7][N:6]2[C:12]=1[CH3:13].[CH3:14][O-:15].[Na+]>CO>[I:11][C:8]1[CH:9]=[CH:10][C:5]2[N:6]([C:12]([CH3:13])=[C:3]([CH2:2][O:15][CH3:14])[N:4]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 119086486HCID 119086486, compound

Product 1

HCID 119086487HCID 119086487, compoundYield 67.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 2-(chloromethyl)-6-iodo-3-methylimidazo[1,2-a]pyridine (150 mg) in MeOH (2.5 ml) was added sodium methoxide (65 mg), and the resulting mixture was heated at reflux for 3 h. The reaction mixture was then cooled to room temperature and concentrated in vacuo. The mixture was diluted with water, and extracted with EtOAc. The extract was washed with brine, dried over Na2SO4 and concentrated in vacuo. The crude product was purified by silica gel column chromatography (MeOH/DCM) to give the title compound (100 mg) as an off-white solid.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 3 h
  3. concentrationconcentrated in vacuo
  4. additionThe mixture was diluted with water
  5. extractionextracted with EtOAc
  6. washThe extract was washed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by silica gel column chromatography (MeOH/DCM)

Sources & evidence

ORD record
ord-7975c6f514af4007bfb71f210c7e9f46
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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