HCID 20066535, compound → HCID 21859619, compound

HRID 358569Notes

Reaction equation

HRID 358569 reaction equation
[N:1]1([C:10]2[CH2:15][CH2:14][CH2:13][C:12](=[O:16])[CH:11]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:7]1[CH:6]=[CH:5][C:4]2[CH2:3][CH2:2][N:1]3[C:9]=2[C:8]=1[C:11]1[C:12](=[O:16])[CH2:13][CH2:14][CH2:15][C:10]=13

Participants

4

Reactant 1

HCID 20066535HCID 20066535, compound

Product 1

HCID 21859619HCID 21859619, compoundYield 14.5%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-(2,3-dihydro-1H-indol-l-yl)-2-cyclohexen-1-one (2.515 g), cupric acetate (4.71 g) and palladium (II) acetate (0.20 g) in dry dimethylformamide (40 ml) was heated at 135° under nitrogen for 4 h. The solvent was then removed under reduced pressure and the residue was suspended in methanol and then filtered. The filtrate was evaporated under reduced pressure and the resultant residue was purified by FCC eluting with ethyl acetate to give the title compound (0.36 g) as a solid. A sample (20 mg) was recrystallised from ethyl acetate to give the title compound (15 mg), m.p. 208°-210°.

Workup

  1. temperaturewas heated at 135° under nitrogen for 4 h
  2. customThe solvent was then removed under reduced pressure
  3. filtrationfiltered
  4. customThe filtrate was evaporated under reduced pressure
  5. customthe resultant residue was purified by FCC
  6. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-20d7ed2d6dfb4a698ae1a0cf66ac6724
Source dataset
uspto-grants-1991_03
Patent number
US04997831

Reaction notes

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