HCID 9837986, compound → HCID 18689906, compound

HRID 1871908Notes

Reaction equation

HRID 1871908 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]3[CH2:17][CH:16]4[N:18]([CH3:19])[CH:13]([CH2:14][CH2:15]4)[CH:12]=3)=[CH:7][NH:8]2)=[CH:4][CH:3]=1>[Pd].CO>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]3[CH2:17][CH:16]4[N:18]([CH3:19])[CH:13]([CH2:14][CH2:15]4)[CH2:12]3)=[CH:7][NH:8]2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 9837986HCID 9837986, compound

Product 1

HCID 18689906HCID 18689906, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 0.233 gm (0.91 mMol) 3-(6-fluoroindol-3-yl)-8-methyl-8-azabicyclo[3.2.1]oct-2-ene and 0.235 gm 10% palladium on carbon in 12 mL methanol was placed under an atmosphere of hydrogen at room temperature. After 8 hours the reaction mixture was filtered and then concentrated under reduced pressure. The residue was again hydrogenated with 0.23 gm 10% palladium on carbon in 7 mL ethanol. After several hours the reaction mixture was filtered and the filtrate concentrated under reduced pressure. The residue was subjected to basic alumina chromatography, eluting with dichloromethane containing 30% dichloromethane saturated with ammonia and 0.5-2% methanol. Fractions containing product were combined and concentrated under reduced pressure to provide 0.068 gm (29%) of the title compound as a colorless solid.

Workup

  1. customwas placed under an atmosphere of hydrogen at room temperature
  2. filtrationAfter 8 hours the reaction mixture was filtered
  3. concentrationconcentrated under reduced pressure
  4. filtrationAfter several hours the reaction mixture was filtered
  5. concentrationthe filtrate concentrated under reduced pressure
  6. washeluting with dichloromethane containing 30% dichloromethane saturated with ammonia and 0.5-2% methanol
  7. additionFractions containing product
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c288fafcd3fe4ee998f7ca19ac3a4322
Source dataset
uspto-grants-2000_08
Patent number
US06107307

Reaction notes

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