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

HRID 1820556Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1820556
[CH3:1][N:2]([CH3:25])[CH:3]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][C:15]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:14]3)=[O:10])[CH2:4]1.[CH:26](CS([O-])(=O)=O)([CH3:28])[CH3:27].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[CH2:23]([O:22][C:20]([C:15]1[N:16]([CH:26]([CH3:28])[CH3:27])[C:17]2[C:13]([CH:14]=1)=[CH:12][C:11]([C:9]([N:5]1[CH2:6][CH2:7][CH2:8][CH:3]([N:2]([CH3:25])[CH3:1])[CH2:4]1)=[O:10])=[CH:19][CH:18]=2)=[O:21])[CH3:24]

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 22141912Isopropyl-methanesulfonateHCID 68680571Ethyl 5-(3-dimethylamino-piperidine-1-carbonyl)-1H-indole-2-carboxylate

Produkt 1

HCID 686800365-(3-Dimethylamino-piperidine-1-carbonyl)-1-isopropyl-1H-indole-2-carboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

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%)

Aufarbeitung

  1. temperatureThe mixture was heated overnight
  2. temperatureat reflux
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue partitioned between water and tert-butylmethyl ether
  5. customThe phases were separated
  6. extractionthe aqueous phase extracted with tert-butylmethyl ether
  7. washthe combined organic phases washed with brine
  8. dry with materialdried over magnesium sulfate
  9. customevaporated under reduced pressure
  10. customThe residue was purified by column chromatography on silica gel (4:1 chloroform/methanol eluant)

Quellen und Nachweise

ORD-Eintrag
ord-86084123834040b5bc2ad0546aad22f5
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07601711B2

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