Dimethylformamide → ethyl 1-cyclopropyl-3-formyl-4-methoxy-1H-indole-6-carboxylate

HRID 420144Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 420144
O=P(Cl)(Cl)Cl.[CH:6]1([N:9]2[C:17]3[C:12](=[C:13]([O:23][CH3:24])[CH:14]=[C:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:16]=3)[CH:11]=[CH:10]2)[CH2:8][CH2:7]1.CN([CH:28]=[O:29])C>CCOC(C)=O.[OH-].[Na+]>[CH:6]1([N:9]2[C:17]3[C:12](=[C:13]([O:23][CH3:24])[CH:14]=[C:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:16]=3)[C:11]([CH:28]=[O:29])=[CH:10]2)[CH2:7][CH2:8]1

Komponenten

6

Edukt 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 66649481ethyl 1-cyclopropyl-4-methoxy-1H-indole-6-carboxylate

Produkt 1

HCID 86621575ethyl 1-cyclopropyl-3-formyl-4-methoxy-1H-indole-6-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

1.28 ml of POCl3 was added dropwise to a solution of 3.24 g of ethyl 1-cyclopropyl-4-methoxy-1H-indole-6-carboxylate in 30 ml of DMF and the mixture was stirred at 0° C. for 2 hrs. The mixture was diluted with EtOAc and 25 ml of 1N NaOH was added. Then the mixture was made basic using saturated NaHCO3aq. The mixture was extracted with EtOAc and the extract was washed with water and saturated brine, dried over Na2SO4, then concentrated. The residue was purified on SiO2 column chromatography (EtOAc-n-Hexane system) to give 2.4 g of ethyl 1-cyclopropyl-3-formyl-4-methoxy-1H-indole-6-carboxylate.

Aufarbeitung

  1. additionwas added
  2. extractionThe mixture was extracted with EtOAc
  3. washthe extract was washed with water and saturated brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified on SiO2 column chromatography (EtOAc-n-Hexane system)

Quellen und Nachweise

ORD-Eintrag
ord-ce40d6d2c83442999f30661b6b7ba9a4
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093389B2

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