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

HRID 506104Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 506104
[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-3d44bf32c45d41818a9b2a1202fe6f7e
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07781478B2

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