Methyl iodide → HCID 15949461, compound

HRID 2220479Notes

Reaction equation

HRID 2220479 reaction equation
[NH2:1][C:2]1[N:3]([CH3:22])[C:4](=[O:21])[C:5]([C:14]2[CH:15]=[C:16]([C:19]#[N:20])[NH:17][CH:18]=2)([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([Br:13])[CH:8]=2)[N:6]=1.[C:23](=O)([O-])[O-].[Cs+].[Cs+].CI>CN(C)C=O.C(Cl)(Cl)Cl>[NH2:1][C:2]1[N:3]([CH3:22])[C:4](=[O:21])[C:5]([C:14]2[CH:15]=[C:16]([C:19]#[N:20])[N:17]([CH3:23])[CH:18]=2)([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([Br:13])[CH:8]=2)[N:6]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 58792269HCID 58792269, compound

Product 1

HCID 15949461HCID 15949461, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-[2-amino-4-(3-bromophenyl)-1-methyl-5-oxo-4,5-dihydro-1H-imidazol-4-yl]-1H-pyrrole-2-carbonitrile (0.50 g, 1.40 mmol) in dimethylformamide was added cesium carbonate (0.639 g, 1.96 mmol) and methyl iodide (96 μL, 1.54 mmol). The reaction mixture was stirred overnight at room temperature while protected from moisture, diluted with chloroform and washed well with water. The organic phase was dried (Na2SO4), filtered through a short column of silica gel and evaporated to afford the desired compound as a tan solid, 0.524 g (quantitative yield).

Workup

  1. washwashed well with water
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. filtrationfiltered through a short column of silica gel
  4. customevaporated

Sources & evidence

ORD record
ord-2ed21f41e19d4f95be930e888e5a232a
Source dataset
uspto-grants-2008_08
Patent number
US07417047B2

Reaction notes

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