Methyl iodide → 4-[4-(3-chloro-phenylethynyl)-2-methyl-imidazol-1-yl]-1-methyl-1H-pyridin-2-one

HRID 2194386Notes

Reaction equation

HRID 2194386 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[N:11]=[C:12]([CH3:22])[N:13]([C:15]3[CH:20]=[CH:19][NH:18][C:17](=[O:21])[CH:16]=3)[CH:14]=2)[CH:5]=[CH:6][CH:7]=1.[C:23](=O)([O-])[O-].[K+].[K+].CI>COCCOC.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[N:11]=[C:12]([CH3:22])[N:13]([C:15]3[CH:20]=[CH:19][N:18]([CH3:23])[C:17](=[O:21])[CH:16]=3)[CH:14]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 498725744-[4-(3-chloro-phenylethynyl)-2-methyl-imidazol-1-yl]-1H-pyridin-2-one

Product 1

HCID 498725754-[4-(3-chloro-phenylethynyl)-2-methyl-imidazol-1-yl]-1-methyl-1H-pyridin-2-oneYield 60%

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 85 mg (0.274 mmol) of 4-[4-(3-chloro-phenylethynyl)-2-methyl-imidazol-1-yl]-1H-pyridin-2-one in 6 ml of DME were added 76 mg (0.55 mmol) of potassium carbonate and 0.034 ml (0.55 mol) of methyl iodide. The suspension was stirred at room temperature for 30 h. The mixture was diluted with 20 ml of ethyl acetate, filtered and concentrated in vaccuo. After purification by flash chromatography on silicagel one obtains 53 mg (0.163 mmol, 60%) of the title compound, as a crystalline yellow solid, MS: m/e=324.2, 326.2 (M+H+).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vaccuo
  3. customAfter purification by flash chromatography on silicagel one

Sources & evidence

ORD record
ord-2701ff25b4ff4ab09ea9b2b1a75e0fca
Source dataset
uspto-grants-2012_12
Patent number
US08334287B2

Reaction notes

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