Reaktion #84200

Reaktionsgleichung

ethyl 6-bromohexanoate

sodium hydride

3-(1-naphthoyl)-1H-indole

→

title compound 2

N-(5-Ethoxycarbonylpentyl)-3-(1-naphthoyl)-1H-indole

Lösungsmittel

DMF

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGwith stirring over a period of 15 min
2. 2
   Temperaturthe mixture was then heated at 60° C. for 3 h
3. 3
   SonstigeThe solvent was removed under high vacuum
4. 4
   Extraktionextracted by ethyl acetate (2×150 ml)
5. 5
   WaschenThe combined ethyl acetate phases were washed by water (1×100 ml), brine (1×100 ml)
6. 6
   Trocknendried over sodium sulphate
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated to dryness
9. 9
   SonstigeThe crude product obtained
10. 10
    Sonstigewas purified by chromatography on silica gel

Vorschrift

To a suspension of sodium hydride (1.1 g, 30 mmol, 60% in mineral oil) in DMF (100 ml) under nitrogen was added solid 3-(1-naphthoyl)-1H-indole 1 (5.43 g, 20 mmol). After stirring at room temperature for 1 h, a solution of ethyl 6-bromohexanoate (6.6 g, 30 mmol) in DMF (10 ml) was added slowly with stirring over a period of 15 min and the mixture was then heated at 60° C. for 3 h. The solvent was removed under high vacuum and the crude product was suspended in water (150 ml) and extracted by ethyl acetate (2×150 ml). The combined ethyl acetate phases were washed by water (1×100 ml), brine (1×100 ml), dried over sodium sulphate filtered and concentrated to dryness. The crude product obtained was purified by chromatography on silica gel using hexane/ethyl acetate (8/2) to give the title compound 2 as an oil which became solid in the cold (7.1 g, 86%).

Quelle