Indole → 1-(4-methoxyphenyl)-1H-indole

HRID 854493Notes

Reaction equation

HRID 854493 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.I[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1.C([O-])([O-])=O.[K+].[K+].O>CN1CCCC1=O.C(OCC)(=O)C>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 798IndoleHCID 962WaterHCID 11430Potassium CarbonateHCID 696764-Iodoanisole

Product 1

HCID 7757151-(4-methoxyphenyl)-1H-indoleYield 70.3%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A slurry of 2.63 g (22.5 mmol) indole, 5.26 g (22.5 mmol) 4-iodoanisole, 0.43 g (3 mmol) CuBr and 4.14 g (30 mmol) K2CO3 in 60 ml anhydrous N-methylpyrrolidinone (NMP) was heated to reflux with stirring for 16 hr. The solution was allowed to cool and then poured into water and shaken with ethyl acetate. The entire biphasic system was filtered through a pad of Celite, the phases were separated, and the organic phase was dried over MgSO4 and concentrated. The crude product was chromatographed on silica (5–7% EtOAc-Hexane) to afford 3.53 g 1-(4-methoxyphenyl)-1H-indole as a colorless solid.

Workup

  1. temperatureto reflux
  2. temperatureto cool
  3. filtrationThe entire biphasic system was filtered through a pad of Celite
  4. customthe phases were separated
  5. dry with materialthe organic phase was dried over MgSO4
  6. concentrationconcentrated
  7. customThe crude product was chromatographed on silica (5–7% EtOAc-Hexane)

Sources & evidence

ORD record
ord-9163f1c5c4fb437aa8c8b2ad30da4295
Source dataset
uspto-grants-2007_08
Patent number
US07259182B2

Reaction notes

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