Water → HCID 66669052, compound

HRID 1617553Notes

Reaction equation

HRID 1617553 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[CH3:25])[CH2:9][C:10]([C:12]2[CH:17]=[CH:16][NH:15][C:14](=[O:18])[CH:13]=2)=[O:11])=[CH:4][CH:3]=1.[C:26](=O)([O-])[O-].[K+].[K+].CI.O>CC(N(C)C)=O.CC(OC)(C)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[CH3:25])[CH2:9][C:10]([C:12]2[CH:17]=[CH:16][N:15]([CH3:26])[C:14](=[O:18])[CH:13]=2)=[O:11])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 66668689HCID 66668689, compound

Product 1

HCID 66669052HCID 66669052, compound

Reagents, catalysts & solvents 2

HCID 15413tert-Butyl methyl etherSolventHCID 31374DimethylacetamideSolvent

Procedure

To a solution of 4-[3-(4-bromo-phenyl)-3-o-tolyl-propionyl]-1H-pyridin-2-one (150 mg) in DMA (1 mL) was added potassium carbonate (58 mg) and methyl iodide (0.06 mL). The mixture was stirred at rt for 6 h, water and TBME were added. The phases were separated and the inorganic phase was extracted with TBME and EtOAc. The combined organic phases were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (EtOAc/n-heptane 1:10 to EtOAc) to yield the title compound as a light yellow foam, MS (ESI+): m/z=410.2 ([M+H]+, 1Br).

Workup

  1. customThe phases were separated
  2. extractionthe inorganic phase was extracted with TBME and EtOAc
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash chromatography on silica gel (EtOAc/n-heptane 1:10 to EtOAc)

Sources & evidence

ORD record
ord-69f3c960a5b3416b9e16b9a7efb462aa
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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