2-Pent-1-ynylaniline → 1H-Indole, 2-propyl-

HRID 1095371Notes

Reaction equation

HRID 1095371 reaction equation
[C:1]([C:6]1[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=1[NH2:8])#[C:2][CH2:3][CH2:4][CH3:5]>[Cu](I)I.CN(C)C=O>[CH2:3]([C:2]1[NH:8][C:7]2[C:6]([CH:1]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:4][CH3:5]

Participants

4

Reactant 1

HCID 109317192-Pent-1-ynylaniline

Product 1

HCID 1394151H-Indole, 2-propyl-Yield 80%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 2-pent-1-ynylaniline (0.25 g, 1.57 mmol), copper iodide (30 mg, 0.16 mmol), and N,N-dimethylformamide (6 mL) was heated at 140° C. for 4 hours and concentrated. The crude material was dissolved in diethyl ether, filtered through a layer of CELITE filter aid, and concentrated under reduced pressure. The residue was purified by automated flash chromatography eluting with a gradient of 0-20% ethyl acetate in hexanes to provide 0.20 g of 2-propyl-1H-indole.

Workup

  1. concentrationconcentrated
  2. dissolutionThe crude material was dissolved in diethyl ether
  3. filtrationfiltered through a layer of CELITE
  4. filtrationfilter aid
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by automated flash chromatography
  7. washeluting with a gradient of 0-20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-5aa99a6c879a4598932154468e8b7a77
Source dataset
uspto-grants-2012_03
Patent number
US08138173B2

Reaction notes

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