Ethanol → Methyl 1-allyl-7-(4-propoxyethoxyphenyl)-2,3-dihydro-1-benzazepine-4-carboxylate

HRID 586980Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 586980
C(O)C.[CH2:4]([N:7]1[C:13]2[CH:14]=[CH:15][C:16](Br)=[CH:17][C:12]=2[CH:11]=[C:10]([C:19]([O:21][CH3:22])=[O:20])[CH2:9][CH2:8]1)[CH:5]=[CH2:6].B([O-])([O-])O[C:25]1[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][O:34][CH2:35][CH2:36][CH3:37])=[CH:27][CH:26]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.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.O>[CH2:4]([N:7]1[C:13]2[CH:14]=[CH:15][C:16]([C:25]3[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][O:34][CH2:35][CH2:36][CH3:37])=[CH:27][CH:26]=3)=[CH:17][C:12]=2[CH:11]=[C:10]([C:19]([O:21][CH3:22])=[O:20])[CH2:9][CH2:8]1)[CH:5]=[CH2:6]

Komponenten

8

Edukt 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 11324721Methyl 1-allyl-7-bromo-2,3-dihydro-1-benzazepine-4-carboxylateHCID 867568144-(2-Propoxyethoxy)phenyl borate

Produkt 1

HCID 69747248Methyl 1-allyl-7-(4-propoxyethoxyphenyl)-2,3-dihydro-1-benzazepine-4-carboxylateAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittel2×HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

In toluene (20 ml), ethanol (2 ml) and water (2 ml) were suspended methyl 1-allyl-7-bromo-2,3-dihydro-1-benzazepine-4-carboxylate (274 mg), 4-propoxyethoxyphenyl borate (248 mg) and potassium carbonate (307 mg), and the suspension was stirred under argon atmosphere for 30 minutes, Then, tetrakistriphenylphosphinepalladium (69 mg) was added thereto, and the mixture was heated under argon atmosphere at 100° C. for 8 hours. After allowing to cool, water was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried with magnesium sulfate. The solvent was evaporated under reduced pressure and the resulting residue was purified with silica gel column chromatography (hexane:ethyl acetate=4:1) to give methyl 1-allyl-7-(4-propoxyethoxyphenyl)-2,3-dihydro-1-benzazepine-4-carboxylate (269 mg) as yellow oil.

Aufarbeitung

  1. temperatureto cool
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried with magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe resulting residue was purified with silica gel column chromatography (hexane:ethyl acetate=4:1)

Quellen und Nachweise

ORD-Eintrag
ord-679d486d1b6846e6bcaafa77d1a0c2bb
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06936602B1

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