Ethanol → 8-Bromo-10-fluoro-2-hydroxy-9-trifluoromethyl-5,11-dihydro-6H-benzo[a]carbazole-3-carboxylic acid

HRID 1690670Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1690670
C[O:2][C:3]([C:5]1[C:27]([OH:28])=[CH:26][C:8]2[C:9]3[NH:10][C:11]4[C:16]([C:17]=3[CH2:18][CH2:19][C:7]=2[CH:6]=1)=[CH:15][C:14]([Br:20])=[C:13]([C:21]([F:24])([F:23])[F:22])[C:12]=4[F:25])=[O:4].C(O)C.O.[Li+].[OH-]>C(OCC)(=O)C>[Br:20][C:14]1[CH:15]=[C:16]2[C:11](=[C:12]([F:25])[C:13]=1[C:21]([F:22])([F:23])[F:24])[NH:10][C:9]1[C:8]3[CH:26]=[C:27]([OH:28])[C:5]([C:3]([OH:4])=[O:2])=[CH:6][C:7]=3[CH2:19][CH2:18][C:17]2=1

Komponenten

6

Edukt 4

HCID 702EthanolHCID 962WaterHCID 3939Lithium HydroxideHCID 160474068-Bromo-10-fluoro-2-hydroxy-9-trifluoromethyl-5,11-dihydro-6H-benzo[a]carbazole-3-carboxylic acid methyl ester

Produkt 1

HCID 160474058-Bromo-10-fluoro-2-hydroxy-9-trifluoromethyl-5,11-dihydro-6H-benzo[a]carbazole-3-carboxylic acidAusbeute 78,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A sample of 8-Bromo-10-fluoro-2-hydroxy-9-trifluoromethyl-5,11-dihydro-6H-benzo[a]carbazole-3-carboxylic acid methyl ester (28.9 mg, 63.4 μmol) is treated with ethanol (0.3 mL) and water (0.5 mL) followed by LiOH (4 mg, 190 μmol). The reaction is then stirred at 50° C. overnight. The reaction is then diluted with ethyl acetate and extracted with 1 M HCl. The organics are then dried over MgSO4, filtered and the solvent is removed. The resulting residue is purified using a UV triggered HPLC to afford 22 mg of the title compound as a white solid; 1H NMR (400 MHz, MeOD) δ 7.78 (s, 1H), 7.76 (s, 1H), 7.32 (s, 1H), 3.00 (m, 2H), 2.95 (2, H); LC/MS calculated for [M+H]+ C18H11F4NO3: 445.1, found: 445.9.

Aufarbeitung

  1. extractionextracted with 1 M HCl
  2. dry with materialThe organics are then dried over MgSO4
  3. filtrationfiltered
  4. customthe solvent is removed
  5. customThe resulting residue is purified

Quellen und Nachweise

ORD-Eintrag
ord-66d475668ef84e18bde2471905e3014f
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153671B2

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