2-(2-Methyl-1-buten-4-yl)indole → Isopentylindol

HRID 1872829Notes

Reaction equation

HRID 1872829 reaction equation
[CH3:1][C:2]([CH2:4][CH2:5][C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH2:3]>[Pd].C(O)C>[CH3:1][CH:2]([CH3:3])[CH2:4][CH2:5][C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2

Participants

4

Reactant 1

HCID 187616282-(2-Methyl-1-buten-4-yl)indole

Product 1

HCID 11041488IsopentylindolYield 59%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Into a 3-necked round bottom flask under a blanket of nitrogen was placed 5% palladium catalyst on charcoal (771 mg). A solution of 2-(2-methyl-1-buten-4-yl) indole (671 mg) in ethanol (36 ml) was added to the flask, which was evacuated and charged with hydrogen twice. The mixture was stirred vigorously under hydrogen (1 atmosphere) for 2 hours, followed by filtration through a pad of Celite. The solvent was removed under reduced pressure and the crude residue was purified by flash chromatography (3% ethyl acetate/hexane) to give 2-(3-methyl-n-butyl)indole (400 mg, 59%) as a yellow crystalline solid.

Workup

  1. customInto a 3-necked round bottom flask under a blanket of nitrogen was placed
  2. customwas evacuated
  3. additioncharged with hydrogen twice
  4. filtrationfollowed by filtration through a pad of Celite
  5. customThe solvent was removed under reduced pressure
  6. customthe crude residue was purified by flash chromatography (3% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-bedbb8cf0f1340d58eaa7c401b2b3cea
Source dataset
uspto-grants-2000_08
Patent number
US06110957

Reaction notes

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