Water → HCID 22328968, Verbindung

HRID 586835Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 586835
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH:12]=[O:13])[CH2:10][CH2:9][C:8]([C:14]([O:16][CH3:17])=[O:15])=[CH:7][C:6]=2[CH:18]=1.B([O-])([O-])O[C:21]1[CH:26]=[CH:25][C:24]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+].O>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.C(O)C>[CH:12]([N:11]1[C:5]2[CH:4]=[CH:3][C:2]([C:21]3[CH:22]=[CH:23][C:24]([N:27]4[CH2:28][CH2:29][O:30][CH2:31][CH2:32]4)=[CH:25][CH:26]=3)=[CH:18][C:6]=2[CH:7]=[C:8]([C:14]([O:16][CH3:17])=[O:15])[CH2:9][CH2:10]1)=[O:13]

Komponenten

8

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 22329262methyl 7-bromo-1-formyl-2,3-dihydro-1H-1-benzazepine-4-carboxylateHCID 86756179HCID 86756179, Verbindung

Produkt 1

HCID 22328968HCID 22328968, VerbindungAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a mixture of methyl 7-bromo-1-formyl-2,3-dihydro-1H-1-benzazepine-4-carboxylate (3.51 g), 4-morpholinophenyl borate (3.51 g) and potassium carbonate (3.75 g) was added a mixture of water (20 ml), ethanol (20 ml) and toluene (100 ml), and the mixture was stirred under argon atmosphere at room temperature for 40 minutes. To the mixture was added tetrakis(triphenylphosphine)palladium (0.52 g), and the mixture was refluxed under argon atmosphere for 12 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, and the residue was purified with silica gel column chromatography (ethyl acetate/hexane) to give methyl 1-formyl-7-(4-morpholinophenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylate (3.64 g) as pale yellow crystals.

Aufarbeitung

  1. additionwas added
  2. temperaturethe mixture was refluxed under argon atmosphere for 12 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe residue was purified with silica gel column chromatography (ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-07f3441d2ee3416e9677d185cb5601e9
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06936602B1

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