Water → HCID 25052168, Verbindung

HRID 502220Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 502220
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:22][CH3:23])[C:10]3[C:15]([C:16]=2[C:17]#[N:18])=[CH:14][CH:13]=[C:12]([O:19][CH2:20][CH3:21])[CH:11]=3)=[CH:4][CH:3]=1.CCN(CC)CC.[CH:31]1([C:34](Cl)=[O:35])[CH2:33][CH2:32]1.O>C1COCC1.C(OCC)(=O)C>[C:17]([C:16]1[C:15]2[C:10](=[CH:11][C:12]([O:19][CH2:20][CH3:21])=[CH:13][CH:14]=2)[N:9]([CH2:22][CH3:23])[C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:34]([CH:31]2[CH2:33][CH2:32]2)=[O:35])=[CH:7][CH:6]=1)#[N:18]

Komponenten

7

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 594252742-(4-aminophenyl)-6-ethoxy-1-ethyl-1H-indole-3-carbonitrile

Produkt 1

HCID 25052168HCID 25052168, VerbindungAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of compound 2-(4-aminophenyl)-6-ethoxy-1-ethyl-1H-indole-3-carbonitrile (3.66 g, 12 mmol), prepared as described in example 1Gb, in 20 mL of THF is added Et3N (3.37 ml) and cyclopropanecarbonyl chloride (1.6 mL, 18 mmol). The mixture is stirred for 3 h at room temperature. Then water and ethyl acetate are added to the reaction mixture. The organic layer is separated, washed with brine (2×), dried over anhydrous Na2SO4, filtered and concentrated. The residue is recrystallized with ethyl acetate and hexane to yield 99% of cyclopropanecarboxylic acid [4-(3-cyano-6-ethoxy-1-ethyl-1H-indol-2-yl)-phenyl]-amide.

Aufarbeitung

  1. customThe organic layer is separated
  2. washwashed with brine (2×)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is recrystallized with ethyl acetate and hexane

Quellen und Nachweise

ORD-Eintrag
ord-904febc561884bdb923c073d01c52dea
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772271B2

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