Triethylamine → HCID 86754350, compound

HRID 1584127Notes

Reaction equation

HRID 1584127 reaction equation
Br[C:2]1[CH:10]=[CH:9][C:8]2[N:7]3[CH2:11][CH:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[NH:13][CH2:14][C:6]3=[CH:5][C:4]=2[CH:3]=1.C(N(CC)CC)C.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C]=O>CO.CS(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:18][O:17][C:15]([C:2]1[CH:10]=[CH:9][C:8]2[N:7]3[CH2:11][CH:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[NH:13][CH2:14][C:6]3=[CH:5][C:4]=2[CH:3]=1)=[O:16]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 812191,3-Bis(diphenylphosphino)propane2×HCID 86754351HCID 86754351, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 86754350HCID 86754350, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalyst2×HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Procedure

A solution of 2-5 (3.0 g, 8.5 mmol) in MeOH (60 mL) and DMSO (20 mL) was treated with triethylamine (3.55 mL, 25.5 mmol), 1,3-Bis(diphenylphosphino)propane (1.75 g, 4.25 mmol) and palladium (II) acetate (0.952 g, 4.25 mmol). Carbon monoxide was bubbled through the solution while it was heated to reflux for 2 hours. The reaction was heated at reflux overnight under a balloon atmosphere of carbon monoxide. Additional 1,3-Bis(diphenylphosphino)propane (0.8 g, 2.12 mmol) and palladium acetate (0.476 g, 2.12 mmol) were added and the reaction was heated at reflux for 48 hours under a balloon atmosphere of carbon monoxide. The reaction was cooled to room temperature, the residue was partitioned between water and EtOAc. The water layer was extracted with EtOAc, the organic layers were combined, washed with water, brine, dried with MgSO4, filtered and evaporated. The residue was chromatographed (25% EtOAc/hexanes) to give 2-6 as a yellow solid.

Workup

  1. customCarbon monoxide was bubbled through the solution while it
  2. temperaturewas heated
  3. temperatureto reflux for 2 hours
  4. temperatureThe reaction was heated
  5. temperatureat reflux overnight under a balloon atmosphere of carbon monoxide
  6. temperaturethe reaction was heated
  7. customthe residue was partitioned between water and EtOAc
  8. extractionThe water layer was extracted with EtOAc
  9. washwashed with water, brine
  10. dry with materialdried with MgSO4
  11. filtrationfiltered
  12. customevaporated
  13. customThe residue was chromatographed (25% EtOAc/hexanes)

Sources & evidence

ORD record
ord-1c5f26d4ed674ae3bbdc692e8785bc09
Source dataset
uspto-grants-1999_08
Patent number
US05932582

Reaction notes

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