Methyl iodide → HCID 67547975, compound

HRID 2356704Notes

Reaction equation

HRID 2356704 reaction equation
[CH2:1]([C:3]1[NH:7][C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)=[N:5][C:4]=1[C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)[CH3:2].[H-].[Na+].[CH3:23]I.[Cl-:25].[NH4+]>CN(C)C=O>[ClH:25].[ClH:25].[CH2:1]([C:3]1[N:7]([CH3:23])[C:6]([C:8]2[CH:9]=[CH:10][C:11]([F:14])=[CH:12][CH:13]=2)=[N:5][C:4]=1[C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)[CH3:2]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 67547196HCID 67547196, compound

Product 1

HCID 67547975HCID 67547975, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-ethyl-2-(4-fluorophenyl)-4-(3-pyridyl)-imidazole (481 mg) in N,N-dimethylformamide (7 ml) was added sodium hydride (79 mg, 60% mineral oil) under ice-acetone cooling, and the mixture was stirred for 15 minutes. To the mixture was added methyl iodide (307 mg) and the mixture was stirred at room temperature for one hour. To the reaction mixture was added a saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The resulting residue was purified by silica gel flush column chromatography (solvent: chloroform:methanol=95:5), and treated with hydrogen chloride-methanol solution to obtain 5-ethyl-2-(4-fluoro-phenyl)-1-methyl-4-(3-pyridyl)imidazole dihydrochloride (285 mg).

Workup

  1. stirringthe mixture was stirred at room temperature for one hour
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe resulting residue was purified by silica gel
  7. customflush column chromatography (solvent: chloroform:methanol=95:5)
  8. additiontreated with hydrogen chloride-methanol solution

Sources & evidence

ORD record
ord-dcc489ff793a40269d607c2bca34ffed
Source dataset
uspto-grants-2010_07
Patent number
US07759373B2

Reaction notes

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