Water → HCID 58424845, compound

HRID 2409429Notes

Reaction equation

HRID 2409429 reaction equation
Cl[C:2]1[N:26]=[CH:25][CH:24]=[CH:23][C:3]=1[C:4]([N:6]([C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:12][CH:11]=1)[CH2:7][O:8][CH3:9])=[O:5].C(P(CCCC)CCCC)CCC.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:9][O:8][CH2:7][N:6]1[C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:12][C:11]=2[C:2]2[N:26]=[CH:25][CH:24]=[CH:23][C:3]=2[C:4]1=[O:5]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 13831TributylphosphineHCID 58424857HCID 58424857, compound

Product 1

HCID 58424845HCID 58424845, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

The compound (55 mg, 0.146 mmol) prepared in step 3 was dissolved in N,N-dimethylformamide (3 ml), sequentially added with palladium(II) acetate (9.83 mg, 0.0438 mmol), 1,3-bis(dephenylphosphino)propane (18 mg, 0.0438 mmol), tributylphosphine (0.036 ml, 0.146 mmol), and potassium carbonate (40 mg, 0.292 mmol). The resulting mixture was refluxed for 5 hours. Water was added to the above solution and the mixture was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate and concentrated to dryness. The residue was then purified by flash column chromatography (hexane:ethyl acetate=3:1) to obtain title compound (31 mg, yield: 64%, white solid).

Workup

  1. temperatureThe resulting mixture was refluxed for 5 hours
  2. extractionthe mixture was extracted with chloroform
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated to dryness
  5. customThe residue was then purified by flash column chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-b2ed582c81384b029075317714809bae
Source dataset
uspto-grants-2014_08
Patent number
US08815891B2

Reaction notes

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