Methyl iodide → HCID 66668567, compound

HRID 1618009Notes

Reaction equation

HRID 1618009 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=2[F:26])[CH2:9][C:10]([C:12]2[CH:13]=[CH:14][C:15](=[O:18])[NH:16][CH:17]=2)=[O:11])=[CH:4][CH:3]=1.[C:27](=O)([O-])[O-].[K+].[K+].IC.C(OCC)(=O)C>CN(C)C(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=2[F:26])[CH2:9][C:10]([C:12]2[CH:13]=[CH:14][C:15](=[O:18])[N:16]([CH3:27])[CH:17]=2)=[O:11])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 66668931HCID 66668931, compound

Product 1

HCID 66668567HCID 66668567, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of 5-(3-(4-bromophenyl)-3-(2,4-difluorophenyl)propanoyl)pyridin-2(1H)-one (0.225 g, 538 μmol) in N,N-dimethylacetamide (3 mL) was added potassium carbonate (81.8 mg, 592 μmol) and iodomethane (80.2 mg, 35.3 μL, 565 μmol) and the resulting mixture was stirred at room temperature for 17 hours. The reaction mixture was poured on water and ethyl acetate and the layers were separated. The aqueous layer was extracted twice with ethyl acetate. The organic layers were washed twice with water and once with brine, dried over magnesium sulfate, filtered, treated with silica gel and evaporated. The compound was purified by silica gel chromatography on a 10 g column using a MPLC system eluting with a gradient of n-heptane:ethyl acetate (100:0 to 0:100). Colourless foam (0.20 g, 86%). MS (ESI+): m/z=432.0 ([M+H]+).

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted twice with ethyl acetate
  3. washThe organic layers were washed twice with water and once with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. additiontreated with silica gel
  7. customevaporated
  8. customThe compound was purified by silica gel chromatography on a 10 g column
  9. washeluting with a gradient of n-heptane:ethyl acetate (100:0 to 0:100)

Sources & evidence

ORD record
ord-0237873dd72044588e2b0554e9eb856b
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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