Carbazole → HCID 67133432, Verbindung

HRID 916164Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 916164
C[O:2][C:3](=[O:32])[CH:4]([NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23](=[O:31])[C:24]1[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=1)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14]Br)=[CH:8][CH:7]=1.[CH:33]1[C:45]2[NH:44][C:43]3[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=3)[C:37]=2[CH:36]=[CH:35][CH:34]=1.[OH-].[Na+]>C1C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:30][C:27]1[CH:26]=[CH:25][C:24]([C:23]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[NH:16][CH:4]([CH2:5][C:6]2[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][C:42]3[C:43]4[NH:44][C:45]5[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=5)[C:38]=4[CH:39]=[CH:40][CH:41]=3)=[CH:8][CH:7]=2)[C:3]([OH:2])=[O:32])=[O:31])=[CH:29][CH:28]=1

Komponenten

6

Edukt 3

HCID 6854CarbazoleHCID 14798Sodium HydroxideHCID 58960086HCID 58960086, Verbindung

Produkt 1

HCID 67133432HCID 67133432, VerbindungAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 241BenzeneLösungsmittel2×

Versuchsvorschrift

To a solution of 2-[(2-(4-methylbenzoyl)phenyl)amino]-3-[4-(2-bromoethoxy)-phenyl]-propionic acid methyl ester (0.24 g, 0.49 mmol) and carbazole (0.082 g, 0.49 mmol) in benzene (10 ml) is added tetrabutyl ammonium bromide (0.08 g) and 50% NaOH aqueous solution (0.084 g, 1.08 mmol), then the mixture is heated to reflux for 10 h. After cooled, benzene (30 ml) is added, and the mixture is washed with water (3×30 ml). Then the solvent is evaporated under a vacuum. The crude product is purified by silica gel chromatography using CHCl3/MeOH (4:1) as eluent to give the title compound (0.15 g, 54%). HRMS calcd for C37H32N2O4: 568.6692. Found: 568.6693. MA calcd for C37H32N2O4: C, 78.15%; H, 5.67%; N, 4.93%. Found: C, 78.36%; H, 5.64%; N, 4.91%.

Aufarbeitung

  1. temperaturethe mixture is heated
  2. temperatureto reflux for 10 h
  3. temperatureAfter cooled
  4. washthe mixture is washed with water (3×30 ml)
  5. customThen the solvent is evaporated under a vacuum
  6. customThe crude product is purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b510584dbb6a439889fa78739707df16
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07268157B2

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