HCID 14973215, compound → HCID 22611233, compound

HRID 725966Notes

Reaction equation

HRID 725966 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]=[C:9]2[C:15]1[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH:16]=1)=[O:5])[CH3:2].[H][H]>C(O)C.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]=[C:9]2[CH:15]1[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 14973215HCID 14973215, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22611233HCID 22611233, compoundYield 55.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 3.24 gm (11.3 mMol) 5-ethoxycarbonyl-3-(1-methyl-1,2,5,6-tetrahydropyridin-4-yl)-1H-indole in 100 mL ethanol was added 0.8 gm 5% palladium an carbon and the reaction mixture hydrogenated at room temperature for 18 hours at an initial hydrogen pressure of 60 p.s.i. The reaction mixture was filtered and the filtrate concentrated under reduced pressure. The residual oil, which crystallized on standing at room temperature, was recrystallized from 30 mL acetonitrile to provide 1.79 gm (55%) of the desired compound as colorless crystals.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customThe residual oil, which crystallized
  4. customon standing at room temperature
  5. customwas recrystallized from 30 mL acetonitrile

Sources & evidence

ORD record
ord-e433a62099934a309261012cad6f63bd
Source dataset
uspto-grants-1998_01
Patent number
US05708008

Reaction notes

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