Dimethylformamide → HCID 59389388, compound

HRID 2357898Notes

Reaction equation

HRID 2357898 reaction equation
[C:1]1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)[CH:6]=CC=C[CH:2]=1.[CH2:30]([C:32]1[CH:49]=[C:35]2[C:36](OS(C(F)(F)F)(=O)=O)=[CH:37][C:38]([F:40])=[CH:39][N:34]2[N:33]=1)[CH3:31].CN(C=[O:54])C>C(OC=CC)C.C(N(CC)CC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:30]([C:32]1[CH:49]=[C:35]2[C:36]([C:2](=[O:54])[CH2:1][CH3:6])=[CH:37][C:38]([F:40])=[CH:39][N:34]2[N:33]=1)[CH3:31]

Participants

7

Reactant 3

HCID 6228Dimethylformamide2×HCID 812191,3-Bis(diphenylphosphino)propaneHCID 59389277HCID 59389277, compound

Product 1

HCID 59389388HCID 59389388, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 8471TriethylamineSolventHCID 13570Ethyl 1-propenyl etherSolvent

Procedure

Palladium acetate (101.8 mg) was dissolved in DMF (25 mL) in an argon atmosphere. To this solution, 1,3-bis(diphenylphosphino)propane (373.9 mg) was added and the mixture was stirred at room temperature for 15 min. Subsequently, the compound of Example 67 (4.25 g) in DMF (65 mL), ethyl-1-propenyl ether (15.0 mL) and triethylamine (3.8 mL) were added and the mixture was stirred at 80° C. for 20 hours. The reaction was terminated by adding water and the mixture was extracted three times with ethyl acetate. The organic layer was washed with saturated brine and dried over sodium sulfate, followed by evaporation of the solvent under reduced pressure. THF (50 mL) and 3 mol/L hydrochloric acid (50 mL) were added and the mixture was stirred at room temperature for 16 hours. Subsequently, the mixture was extracted three times with ethyl acetate. The organic layer was washed with saturated brine and dried over sodium sulfate. Evaporation of the solvent under reduced pressure and purification by silica gel column chromatography (hexane:ethyl acetate=6:1) afforded the title compound as a yellow powder (670 mg).

Workup

  1. stirringthe mixture was stirred at 80° C. for 20 hours
  2. customThe reaction was terminated
  3. additionby adding water
  4. extractionthe mixture was extracted three times with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over sodium sulfate
  7. customfollowed by evaporation of the solvent under reduced pressure
  8. additionTHF (50 mL) and 3 mol/L hydrochloric acid (50 mL) were added
  9. stirringthe mixture was stirred at room temperature for 16 hours
  10. extractionSubsequently, the mixture was extracted three times with ethyl acetate
  11. washThe organic layer was washed with saturated brine
  12. dry with materialdried over sodium sulfate
  13. customEvaporation of the solvent
  14. customunder reduced pressure and purification by silica gel column chromatography (hexane:ethyl acetate=6:1)

Sources & evidence

ORD record
ord-e9e6cf7f0b404b5e8a2052d84bb28aa0
Source dataset
uspto-grants-2010_07
Patent number
US07763617B2

Reaction notes

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