Water → HCID 58424897, compound

HRID 2409448Notes

Reaction equation

HRID 2409448 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:11]=[C:12]([CH:18]=[C:19]([O:21][CH3:22])[CH:20]=1)[C:13]([O:15][CH2:16][CH3:17])=[O:14])[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.ClCCl>[CH3:22][O:21][C:19]1[C:20]2[C:2]3[N:26]=[CH:25][CH:24]=[CH:23][C:3]=3[C:4](=[O:5])[N:6]([CH2:7][O:8][CH3:9])[C:10]=2[CH:11]=[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:18]=1

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 13831TributylphosphineHCID 58424921HCID 58424921, compound

Product 1

HCID 58424897HCID 58424897, compoundYield 77.3%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

The compound (1.11 g, 2.94 mmol) prepared in step 5 was dissolved in N,N-dimethylformamide (10.0 ml), added with palladium(II) acetate (215 mg, 0.881 mmol), 1,3-bis(dephenylphosphino)propane (363 mg, 0.881 mmol), tributylphosphine (0.724 ml, 2.94 mmol), and potassium carbonate (812 mg, 5.87 mmol). The resulting mixture was refluxed for 3 hours and cooled to room temperature. Water and dichloromethane were added and the mixture was extracted. The organic layer was dried over anhydrous magnesium sulfate and concentrated to dryness. The residue was then purified by flash column chromatography (dichloromethane:ethyl acetate=4:1) to obtain the title compound (776.5 mg, yield: 77.3%, white solid).

Workup

  1. temperatureThe resulting mixture was refluxed for 3 hours
  2. extractionthe mixture was extracted
  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 (dichloromethane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-cf36ee18047148ac9f6097141f01136e
Source dataset
uspto-grants-2014_08
Patent number
US08815891B2

Reaction notes

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