Water → Cyclopropanecarboxylic acid{4-[6-(2-chloroethoxy)-3-cyano-1-ethyl-1h-indol-2-yl]-phenyl}-amide

HRID 252592Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 252592
[C:1]([C:3]1[C:11]2[C:6](=[CH:7][C:8]([OH:12])=[CH:9][CH:10]=2)[N:5]([CH2:13][CH3:14])[C:4]=1[C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]([CH:24]2[CH2:26][CH2:25]2)=[O:23])=[CH:17][CH:16]=1)#[N:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:34][CH2:35][Cl:36].O>CCC(C)=O.C(OCC)(=O)C>[Cl:36][CH2:35][CH2:34][O:12][C:8]1[CH:7]=[C:6]2[C:11]([C:3]([C:1]#[N:2])=[C:4]([C:15]3[CH:20]=[CH:19][C:18]([NH:21][C:22]([CH:24]4[CH2:26][CH2:25]4)=[O:23])=[CH:17][CH:16]=3)[N:5]2[CH2:13][CH3:14])=[CH:10][CH:9]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 59425200cyclopropanecarboxylic acid [4-(3-cyano-1-ethyl-6-hydroxy-1H-indol-2-yl)-phenyl]-amide

Produkt 1

HCID 59426127Cyclopropanecarboxylic acid{4-[6-(2-chloroethoxy)-3-cyano-1-ethyl-1h-indol-2-yl]-phenyl}-amideAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6569Methyl Ethyl KetoneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of cyclopropanecarboxylic acid [4-(3-cyano-1-ethyl-6-hydroxy-1H-indol-2-yl)-phenyl]-amide (4 g, 11.6 mmol) in 15 mL of MEK is added K2CO3 (8 g, 58 mmol) and 1-bromo-2-chloro-ethane (6.7 mL, 70 mmol). Then the mixture is heated at reflux overnight. After it is cooled to room temperature, water and ethyl acetate are added. The organic layer is separated, washed with brine (2×), dried over anhydrous Na2SO4, filtered and concentrated to yield 81% of the crude cyclopropanecarboxylic acid {4-[6-(2-chloroethoxy)-3-cyano-1-ethyl-1H-indol-2-yl]-phenyl}-amide.

Aufarbeitung

  1. temperatureThen the mixture is heated
  2. temperatureat reflux overnight
  3. customThe organic layer is separated
  4. washwashed with brine (2×)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-236142065b7443b9890fb762779aaf8c
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07868037B2

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