HCID 18351782, compound → HCID 18351596, compound

HRID 430776Notes

Reaction equation

HRID 430776 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]2[C:20]3[C:15](=[C:16]([O:21]CC4C=CC=CC=4)[CH:17]=[CH:18][CH:19]=3)[CH:14]=[CH:13]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H][H]>[Pd].CO>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]2[C:20]3[C:15](=[C:16]([OH:21])[CH:17]=[CH:18][CH:19]=3)[CH:14]=[CH:13]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 18351782HCID 18351782, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18351596HCID 18351596, compoundYield 71.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Under argon atmosphere, 1-(5-phenylpentyl)-4-benzyloxyindole (330 mg) and 5% Pd-C (10 mg) were added to methanol (5 ml) and the atmosphere in the reaction vessel was replaced with hydrogen. The mixture was stirred at room temperature for 2 hours and solids were removed by filtration through Celite. The solvent was removed under reduced pressure, and the obtained crude product was purified by silica gel column chromatography to obtain the desired compound (178 mg, yield: 71%).

Workup

  1. customsolids were removed by filtration through Celite
  2. customThe solvent was removed under reduced pressure
  3. customthe obtained crude product
  4. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-cf11014a11764f74a76e3b5db523b95a
Source dataset
uspto-grants-2001_11
Patent number
US06323235B1

Reaction notes

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