Methyl iodide → HCID 59389287, compound

HRID 2357915Notes

Reaction equation

HRID 2357915 reaction equation
[CH2:1]([C:3]1[CH:18]=[C:6]2[C:7]([C:11](=[O:17])[CH2:12][C:13]([O:15][CH3:16])=[O:14])=[CH:8][CH:9]=[CH:10][N:5]2[N:4]=1)[CH3:2].[H-].[Na+].[CH3:21]I.[Cl-].[NH4+]>CN(C)C=O>[CH2:1]([C:3]1[CH:18]=[C:6]2[C:7]([C:11](=[O:17])[CH:12]([CH3:21])[C:13]([O:15][CH3:16])=[O:14])=[CH:8][CH:9]=[CH:10][N:5]2[N:4]=1)[CH3:2]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 59389405HCID 59389405, compound

Product 1

HCID 59389287HCID 59389287, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound of Example 180 (830 mg) was dissolved in N,N-dimethylformamide (50 mL) in a stream of argon gas and 60% sodium hydride (135 mg) was added while the solution was stirred in an ice bath. The resulting mixture was stirred at room temperature for 15 min, followed by chilling in an ice bath and addition of methyl iodide (210 μL). The mixture was then stirred at room temperature for 3 hours. Subsequently, a saturated aqueous solution of ammonium chloride was added and the mixture was extracted with ethyl acetate. The organic layer was washed sequentially with water (×2) and saturated brine and dried over anhydrous sodium sulfate. Evaporation of the solvent and subsequent purification of the residue by silica gel column chromatography (hexane:ethyl acetate=3:1) afforded the title compound as a pale yellow oil (700 mg).

Workup

  1. additionwas added while the solution
  2. stirringThe resulting mixture was stirred at room temperature for 15 min
  3. temperatureby chilling in an ice bath
  4. stirringThe mixture was then stirred at room temperature for 3 hours
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed sequentially with water (×2) and saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customEvaporation of the solvent and subsequent purification of the residue by silica gel column chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-136fabe1556a4d5bae5de4cb6aa0c7cb
Source dataset
uspto-grants-2010_07
Patent number
US07763617B2

Reaction notes

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