Ethanol → methyl 7-[4-(2-butoxyethoxy)phenyl]-1-(N,N-dimethyl-4-sulfamoylphenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylate

HRID 586948Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 586948
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:12]3[CH:17]=[CH:16][C:15]([S:18](=[O:23])(=[O:22])[N:19]([CH3:21])[CH3:20])=[CH:14][CH:13]=3)[CH2:10][CH2:9][C:8]([C:24]([O:26][CH3:27])=[O:25])=[CH:7][C:6]=2[CH:28]=1.B([O-])([O-])O[C:31]1[CH:36]=[CH:35][C:34]([O:37][CH2:38][CH2:39][O:40][CH2:41][CH2:42][CH2:43][CH3:44])=[CH:33][CH:32]=1.C(=O)([O-])[O-].[K+].[K+].C(O)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[CH2:41]([O:40][CH2:39][CH2:38][O:37][C:34]1[CH:33]=[CH:32][C:31]([C:2]2[CH:3]=[CH:4][C:5]3[N:11]([C:12]4[CH:13]=[CH:14][C:15]([S:18](=[O:23])(=[O:22])[N:19]([CH3:20])[CH3:21])=[CH:16][CH:17]=4)[CH2:10][CH2:9][C:8]([C:24]([O:26][CH3:27])=[O:25])=[CH:7][C:6]=3[CH:28]=2)=[CH:36][CH:35]=1)[CH2:42][CH2:43][CH3:44]

Komponenten

7

Edukt 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 22328934methyl 7-bromo-1-(N,N-dimethyl-4-sulfamoylphenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylateHCID 867568154-Butoxyethoxyphenyl borate

Produkt 1

HCID 22328993methyl 7-[4-(2-butoxyethoxy)phenyl]-1-(N,N-dimethyl-4-sulfamoylphenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylateAusbeute 80,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of methyl 7-bromo-1-(N,N-dimethyl-4-sulfamoylphenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylate (0.35 g), 4-(2-butoxyethoxy)phenyl borate (0.19 g), 1M potassium carbonate solution (2 ml), ethanol (2 ml) and toluene (50 ml) was stirred under argon atmosphere at room temperature for 30 minutes. To the mixture was added tetrakis(triphenylphosphine)palladium (0.04 g), and the mixture was refluxed under argon atmosphere for 6 hours and extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried with anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified with silica gel column chromatography (ethyl acetate/hexane) to give methyl 7-[4-(2-butoxyethoxy)phenyl]-1-(N,N-dimethyl-4-sulfamoylphenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylate (0.35 g) as colorless crystals.

Aufarbeitung

  1. temperaturethe mixture was refluxed under argon atmosphere for 6 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified with silica gel column chromatography (ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-ae80f33a069e4261bafceab0d7c16472
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06936602B1

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