Sodium hydride → N-(5-Ethoxycarbonylpentyl)-3-(1-naphthoyl)-1H-indole

HRID 55922

Reaktionsgleichung

Reaktionsgleichung von HRID 55922
[H-].[Na+].[C:3]1([C:13]([C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[NH:17][CH:16]=2)=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.Br[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31]>CN(C=O)C>[CH2:33]([O:32][C:30]([CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][N:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:15]([C:13]([C:3]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH:6]=[CH:5][CH:4]=2)=[O:14])=[CH:16]1)=[O:31])[CH3:34]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 117544Ethyl 6-bromohexanoateHCID 103558253-Naphthoylindole

Produkt 1

HCID 68159362N-(5-Ethoxycarbonylpentyl)-3-(1-naphthoyl)-1H-indole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

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%).

Aufarbeitung

  1. stirringwith stirring over a period of 15 min
  2. temperaturethe mixture was then heated at 60° C. for 3 h
  3. customThe solvent was removed under high vacuum
  4. extractionextracted by ethyl acetate (2×150 ml)
  5. washThe combined ethyl acetate phases were washed by water (1×100 ml), brine (1×100 ml)
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. customThe crude product obtained
  10. customwas purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-f58b4648f40e4319b79e4983a18f7599
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434687B2

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