Sodium Iodide → methyl 3-(5-cyano-1H-indol-3-yl)propanoate

HRID 1647787Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1647787
[CH3:1][O:2][C:3]([CH:5]([CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20]#[N:21])[CH:18]=2)[NH:13][CH:12]=1)C(OC)=O)=[O:4].[I-].[Na+]>N1C=CC=CC=1.C(Cl)(Cl)Cl>[C:20]([C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[C:11]2[CH2:10][CH2:5][C:3]([O:2][CH3:1])=[O:4])#[N:21]

Komponenten

5

Edukt 2

HCID 5238Sodium IodideHCID 19921655methyl 2-methoxycarbonyl-3-(5-cyano-1H-indol-3-yl)propanoate

Produkt 1

HCID 19921624methyl 3-(5-cyano-1H-indol-3-yl)propanoateAusbeute 80.799,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To a solution of 1.14 g (3.98 mmol, 1.0 equiv.) of methyl 2-methoxycarbonyl-3-(5-cyano-1 H-indol-3-yl)propanoate in 20 mL of pyridine was added 1.19 g (7.96 mmol, 2.0 equiv.) of sodium iodide. The mixture was heated to reflux for sixteen hours. The solution was cooled and diluted with 150 mL of chloroform. The organic layer was washed once with 25 mL of saturated aqueous sodium bicarbonate solution. The organic layer was separated, dried over anhydrous sodium sulfate, filtered and concentrated. The resulting residue was filtered through a plug of silica gel with 1:1 ethyl acetate:hexane to remove colored impurities to provide 0,734 g (81%) of methyl 3-(5-cyano-1H-indol-3-yl)propanoate.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux for sixteen hours
  3. temperatureThe solution was cooled
  4. washThe organic layer was washed once with 25 mL of saturated aqueous sodium bicarbonate solution
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. filtrationThe resulting residue was filtered through a plug of silica gel with 1:1 ethyl acetate
  10. customhexane to remove colored impurities

Quellen und Nachweise

ORD-Eintrag
ord-57118cae55d24259871a053e932212b8
Quelldatensatz
uspto-grants-1995_07
Patentnummer
US05434154

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