Potassium Carbonate → 7-(4-ethylphenyl)-1-methyl-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1-benzoazepine-4-carboxamide

HRID 566058Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 566058
B([O-])([O-])O[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH3:10])=[CH:5][CH:4]=1.Br[C:14]1[CH:15]=[CH:16][C:17]2[N:23]([CH3:24])[CH2:22][CH2:21][C:20]([C:25]([NH:27][C:28]3[CH:33]=[CH:32][C:31]([CH2:34][N:35]([CH3:42])[CH:36]4[CH2:41][CH2:40][O:39][CH2:38][CH2:37]4)=[CH:30][CH:29]=3)=[O:26])=[CH:19][C:18]=2[CH:43]=1.C(=O)([O-])[O-].[K+].[K+]>O.C(O)C.C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:9]([C:6]1[CH:7]=[CH:8][C:3]([C:14]2[CH:15]=[CH:16][C:17]3[N:23]([CH3:24])[CH2:22][CH2:21][C:20]([C:25]([NH:27][C:28]4[CH:29]=[CH:30][C:31]([CH2:34][N:35]([CH3:42])[CH:36]5[CH2:37][CH2:38][O:39][CH2:40][CH2:41]5)=[CH:32][CH:33]=4)=[O:26])=[CH:19][C:18]=3[CH:43]=2)=[CH:4][CH:5]=1)[CH3:10]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 223290367-bromo-1-methyl-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1-benzoazepine-4-carboxamideHCID 867561644-Ethylphenyl borate

Produkt 1

HCID 184725257-(4-ethylphenyl)-1-methyl-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1-benzoazepine-4-carboxamideAusbeute 39,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 86587398Ethanol toluene waterLösungsmittel

Versuchsvorschrift

In water:ethanol:toluene (1:1:10, 18.0 ml) were dissolved 4-ethylphenyl borate (227 mg) and 7-bromo-1-methyl-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1-benzoazepine-4-carboxamide (611 mg), and to the mixture was added potassium carbonate (418 mg). The mixture was stirred under argon atmosphere for 30 minutes, and to the mixture was added tetrakistriphenylphosphine palladium (59 mg). Under argon atmosphere, the mixture was refluxed for 17 hours, and the mixture was diluted with ethyl acetate (200 ml) and washed with water (50 ml) and saturated brine (50 ml). The organic layer was dried with anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified with silica gel column chromatography (75 g, ethyl acetate:ethanol=9:1) and recrystallized from ethanol to give 7-(4-ethylphenyl)-1-methyl-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1-benzoazepine-4-carboxamide (Compound 307) (252 mg, 39%).

Aufarbeitung

  1. temperatureUnder argon atmosphere, the mixture was refluxed for 17 hours
  2. washwashed with water (50 ml) and saturated brine (50 ml)
  3. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified with silica gel column chromatography (75 g, ethyl acetate:ethanol=9:1)
  6. customrecrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-458c98cd9212422ea6c27a857041140f
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06172061B2

Notizen zur Reaktion

Wird geladen…