5-Methoxyindole-2-carboxylic acid → HCID 489420, Verbindung

HRID 2395786Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2395786
C(N1[CH:12]=[CH:11]N=C1)(N1C=CN=C1)=O.[CH3:13][O:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][C:19]([C:24]([OH:26])=O)=[CH:18]2.C(N[C:31]1[C:32]([N:37]2[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]2)=N[CH:34]=[CH:35][CH:36]=1)CC.[C:43](=O)(O)[O-:44].[Na+]>O1CCCC1.CCOCC>[CH3:11][CH2:12][O:44][C:43]1[C:32]([N:37]2[CH2:38][CH2:39][N:40]([C:24]([C:19]3[NH:20][C:21]4[CH:22]=[CH:23][C:15]([O:14][CH3:13])=[CH:16][C:17]=4[CH:18]=3)=[O:26])[CH2:41][CH2:42]2)=[CH:31][CH:36]=[CH:35][CH:34]=1

Komponenten

7

Edukt 4

HCID 204015-Methoxyindole-2-carboxylic acidHCID 682631,1'-CarbonyldiimidazoleHCID 516892Sodium BicarbonateHCID 10331071HCID 10331071, Verbindung

Produkt 1

HCID 489420HCID 489420, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

1,1'-Carbonyldiimidazole (1.30 g) is added to a 20°-25° solution of 5-methoxyindole-2-carboxylic acid (I, 1.39) in tetrahydrofuran (14 ml). The reaction is stirred one hour, then cooled to 0° and 1-(2-ethoxyphenyl)piperazine (II, 1.50 g) dissolved in tetrahydrofuran (7 ml) is added via cannula. The reaction is warmed to 20°-25° and stirred 48 hours. The reaction is diluted with ether (100 ml), poured into saturated aqueous sodium bicarbonate (100 ml). The organic layers are separated and washed with saline (100 ml), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue is recrystallized from toluene to give the title compound, mp 105°-107°.

Aufarbeitung

  1. temperaturecooled to 0°
  2. additionis added via cannula
  3. temperatureThe reaction is warmed to 20°-25°
  4. stirringstirred 48 hours
  5. customThe organic layers are separated
  6. washwashed with saline (100 ml)
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue is recrystallized from toluene

Quellen und Nachweise

ORD-Eintrag
ord-408ec4260d9848dcba9d77df25e256c9
Quelldatensatz
uspto-grants-1996_02
Patentnummer
US05489593

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