Reaktion #1907738

Reaktionsgleichung

ethyl 5-(3-dimethylamino-piperidine-1-carbonyl)-1H-indole-2-carboxylate

isopropylmethane-sulfonate

caesium carbonate

→

product

5-(3-Dimethylamino-piperidine-1-carbonyl)-1-isopropyl-1H-indole-2-carboxylic acid ethyl ester

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was heated overnight
2. 2
   Temperaturat reflux
3. 3
   SonstigeThe solvent was evaporated under reduced pressure
4. 4
   Sonstigethe residue partitioned between water and tert-butylmethyl ether
5. 5
   SonstigeThe phases were separated
6. 6
   Extraktionthe aqueous phase extracted with tert-butylmethyl ether
7. 7
   Waschenthe combined organic phases washed with brine
8. 8
   Trocknendried over magnesium sulfate
9. 9
   Sonstigeevaporated under reduced pressure
10. 10
    SonstigeThe residue was purified by column chromatography on silica gel (4:1 chloroform/methanol eluant)

Vorschrift

To a solution of ethyl 5-(3-dimethylamino-piperidine-1-carbonyl)-1H-indole-2-carboxylate (1.51 g, 4 mmol) in acetonitrile (30 ml) were added isopropylmethane-sulfonate (1.8 eq, 1.1 g) and caesium carbonate (1.8 eq, 2.6 g). The mixture was heated overnight at reflux. The solvent was evaporated under reduced pressure and the residue partitioned between water and tert-butylmethyl ether. The phases were separated, the aqueous phase extracted with tert-butylmethyl ether and the combined organic phases washed with brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (4:1 chloroform/methanol eluant) to afford the product as a light-brown gum. (31%)

Quelle