Methyl iodide → HCID 59635789, compound

HRID 1191860Notes

Reaction equation

HRID 1191860 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][N:7]([CH2:10][CH:11]([CH3:14])[CH2:12][OH:13])[C:6](=[O:15])[CH:5]=1.[CH3:16]I>CN(C)C=O>[Br:3][C:4]1[CH:9]=[CH:8][N:7]([CH2:10][CH:11]([CH3:14])[CH2:12][O:13][CH3:16])[C:6](=[O:15])[CH:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59635809HCID 59635809, compound

Product 1

HCID 59635789HCID 59635789, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (60% in mineral oil, 57 mg) was added to a solution of 4-bromo-1-(3-hydroxy-2-methyl-propyl)-1H-pyridin-2-one (0.53 g) in dimethylformamide (6 mL) chilled in an ice bath. After stirring the solution with cooling for 0.5 h, methyl iodide (110 μL) was added. The cooling bath was removed and the solution was stirred at room temperature overnight. Then, the solution was concentrated under reduced pressure and the residue was diluted with water. The resulting mixture was extracted with ethyl acetate and the combined organic extracts were washed with brine and dried (MgSO4). The solvent was evaporated and the residue was purified by HPLC on reversed phase (acetonitrile/water) to give the title compound as an oil. Yield: 70 mg (30% of theory); Mass spectrum (ESI+): m/z=260/262 (Br) [M+H]+.

Workup

  1. temperaturechilled in an ice bath
  2. temperaturewith cooling for 0.5 h
  3. customThe cooling bath was removed
  4. stirringthe solution was stirred at room temperature overnight
  5. concentrationThen, the solution was concentrated under reduced pressure
  6. additionthe residue was diluted with water
  7. extractionThe resulting mixture was extracted with ethyl acetate
  8. washthe combined organic extracts were washed with brine
  9. dry with materialdried (MgSO4)
  10. customThe solvent was evaporated
  11. customthe residue was purified by HPLC on reversed phase (acetonitrile/water)

Sources & evidence

ORD record
ord-af4ac52a0dce4ee6b6e777850e9f7219
Source dataset
uspto-grants-2014_03
Patent number
US08680093B2

Reaction notes

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