Reaktion #65165

ord-004b306ad62141d38d2ed9eea186b3c9

Reaktionsgleichung

Cc1ccccc1
toluene
Cc1[nH]c2ccc(Cl)cc2c1SC1CCNCC1
5-chloro-2-methyl-3-(piperidin-4-ylthio)-1H-indole
O=C([O-])[O-].[Na+].[Na+]
sodium carbonate
ICCn1cccc1
1-(2-iodoethyl)-1H-pyrrole
Cc1[nH]c2ccc(Cl)cc2c1SC1CCN(CCn2cccc2)CC1
5-chloro-2-methyl-3-[[1-[2-(1H-pyrrol-1-yl)ethyl]piperidin-4-yl]thio]-1H-indole

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperatur(1983) 61, 454-60) is refluxed for 15 hours
  2. 2
    TrocknenThe organic phase is dried over magnesium sulfate
  3. 3
    Einengenconcentrated
  4. 4
    SonstigeThe residue is chromatographed on silica gel (eluent: CH2Cl2 /MeOH:90/10)

Vorschrift

A toluene solution (100 ml) of 5-chloro-2-methyl-3-(piperidin-4-ylthio)-1H-indole (1.09 g, prepared in Example 18), sodium carbonate (0.78 g) and 1-(2-iodoethyl)-1H-pyrrole (0.92 g, prepared according to GALEAZZI, E.; GUZMAN, A.; PINEDO, A.; SALDANA, A.; TORRE, D.; MUCHOWSKI, J. M., Can. J. Chem. (1983) 61, 454-60) is refluxed for 15 hours. The reaction mixture is taken up in a water/dichloromethane mixture. The organic phase is dried over magnesium sulfate and concentrated. The residue is chromatographed on silica gel (eluent: CH2Cl2 /MeOH:90/10) to give 5-chloro-2-methyl-3-[[1-[2-(1H-pyrrol-1-yl)ethyl]piperidin-4-yl]thio]-1H-indole (0.9 g).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05418242uspto-grants-1995_05