Chlorosuccinimide → ethyl-3-chloro-1-cyclopropyl-4-(methoxy)-1H-indole-6-carboxylate

HRID 420146Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 420146
[CH:1]1([N:4]2[C:12]3[C:7](=[C:8]([O:18][CH3:19])[CH:9]=[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:11]=3)[CH:6]=[CH:5]2)[CH2:3][CH2:2]1.[Cl:20]N1C(=O)CCC1=O>C1COCC1.CCOC(C)=O>[CH2:16]([O:15][C:13]([C:10]1[CH:11]=[C:12]2[C:7]([C:6]([Cl:20])=[CH:5][N:4]2[CH:1]2[CH2:2][CH2:3]2)=[C:8]([O:18][CH3:19])[CH:9]=1)=[O:14])[CH3:17]

Komponenten

5

Edukt 2

HCID 31398ChlorosuccinimideHCID 66649481ethyl 1-cyclopropyl-4-methoxy-1H-indole-6-carboxylate

Produkt 1

HCID 66649552ethyl-3-chloro-1-cyclopropyl-4-(methoxy)-1H-indole-6-carboxylateAusbeute 70,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a stirred solution of 1.29 g of ethyl 1-cyclopropyl-4-methoxy-1H-indole-6-carboxylate in 13 ml of THF was added 801 mg of N-chlorosuccinimide and the mixture was stirred at 60° C. for 2 hrs. After diluted with EtOAc, the mixture was washed successively with water and saturated brine, dried over Na2SO4, and concentrated. The residue was purified on SiO2 column chromatography to afford 1.03 g of ethyl-3-chloro-1-cyclopropyl-4-(methoxy)-1H-indole-6-carboxylate as a colorless solid.

Aufarbeitung

  1. washthe mixture was washed successively with water and saturated brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified on SiO2 column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-df492794a6df4779bd733cdb7b24cbad
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093389B2

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