Potassium Carbonate → HCID 58425000, compound

HRID 2409394Notes

Reaction equation

HRID 2409394 reaction equation
Cl[C:2]1[N:27]=[CH:26][CH:25]=[CH:24][C:3]=1[C:4]([N:6]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[CH:8]=1)=[O:5].C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(P(CCCC)CCCC)CCC.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:14][O:13][C:9]1[CH:10]=[CH:11][C:12]2[C:2]3[N:27]=[CH:26][CH:25]=[CH:24][C:3]=3[C:4](=[O:5])[N:6]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[C:7]=2[CH:8]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 13831TributylphosphineHCID 812191,3-Bis(diphenylphosphino)propaneHCID 58424909HCID 58424909, compound

Product 1

HCID 58425000HCID 58425000, compoundYield 24.4%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a stirred solution of the compound (873 mg, 2.28 mmol) prepared in step 2 in N,N-dimethylformamide (6.0 ml), were added sequently palladium(II) acetate (153.6 mg, 0.684 mmol), 1,3-bis(diphenylphosphino)propane (282 mg, 0.684 mmol), tributylphosphine (0.563 ml, 2.28 mmol), and potassium carbonate (630 mg, 4.56 mmol) and the mixture was refluxed for four hours at 120° C. Once the reaction was completed, the reaction mixture was cooled to a room temperature and extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by flash column chromatography (hexane:ethyl acetate:dichloromethane=1:1:1) to obtain the title compound (192.4 mg, yield: 24%, white solid).

Workup

  1. temperaturethe reaction mixture was cooled to a room temperature
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash column chromatography (hexane:ethyl acetate:dichloromethane=1:1:1)

Sources & evidence

ORD record
ord-17bd4a5c6ba342d3a3066b153fb7786c
Source dataset
uspto-grants-2014_08
Patent number
US08815891B2

Reaction notes

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