Methyl iodide → 2-[(1S)-1-(2,3-dimethylphenyl)ethyl]-1-methyl-1h-imidazole

HRID 1985882Notes

Reaction equation

HRID 1985882 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C@@H:9]([C:11]1[NH:12][CH:13]=[CH:14][N:15]=1)[CH3:10].[C:16](=O)([O-])[O-].[Cs+].[Cs+].IC>CC(C)=O>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C@@H:9]([C:11]1[N:15]([CH3:16])[CH:14]=[CH:13][N:12]=1)[CH3:10]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 24738933Demiditraz

Product 1

HCID 577184342-[(1S)-1-(2,3-dimethylphenyl)ethyl]-1-methyl-1h-imidazole

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of the compound of Example 58 (100 mg, 0.5 mmol) and caesium carbonate (407 mg, 1.25 mmol) in acetone (4 ml) was added iodomethane (78 μl, 1.25 mmol). The reaction mixture was stirred at room temperature, under nitrogen, for 4 h and then concentrated in vacuo. to the residue was added water (10 ml) and the solution was extracted with ethyl acetate (2×10 ml). The combined extracts were dried (MgSO4) and concentrated in vacuo.

Workup

  1. concentrationconcentrated in vacuo
  2. additionto the residue was added water (10 ml)
  3. extractionthe solution was extracted with ethyl acetate (2×10 ml)
  4. dry with materialThe combined extracts were dried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-607735f567d14ac79d2c97219907ed9a
Source dataset
uspto-grants-2009_06
Patent number
US07547718B2

Reaction notes

Loading…