Methyl iodide → HCID 15949461, compound

HRID 646264Notes

Reaction equation

HRID 646264 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-53e8de5d06984c7dba8e9e020bc5e7d5
Source dataset
uspto-grants-2010_04
Patent number
US07705030B2

Reaction notes

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