Ethanol → Methyl 7-(4-butoxyethoxyphenyl)-1-(3-methoxybenzyl)-2,3-dihydro-1-benzazepine-4-carboxylic acid

HRID 586988Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 586988
[CH2:1](O)C.Br[C:5]1[CH:6]=[CH:7][C:8]2[N:14]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=3)[CH2:13][CH2:12][C:11]([C:24]([OH:26])=[O:25])=[CH:10][C:9]=2[CH:27]=1.B([O-])([O-])O[C:30]1[CH:35]=[CH:34][C:33]([O:36][CH2:37][CH2:38][O:39][CH2:40][CH2:41][CH2:42][CH3:43])=[CH:32][CH:31]=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>[CH3:1][CH:13]1[CH2:12][C:11]([C:24]([OH:26])=[O:25])=[CH:10][C:9]2[CH:27]=[C:5]([C:30]3[CH:35]=[CH:34][C:33]([O:36][CH2:37][CH2:38][O:39][CH2:40][CH2:41][CH2:42][CH3:43])=[CH:32][CH:31]=3)[CH:6]=[CH:7][C:8]=2[N:14]1[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=1

Komponenten

8

Edukt 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 223289287-Bromo-1-(3-methoxybenzyl)-2,3-dihydro-1-benzazepine-4-carboxylic acidHCID 867568154-Butoxyethoxyphenyl borate

Produkt 1

HCID 22329269Methyl 7-(4-butoxyethoxyphenyl)-1-(3-methoxybenzyl)-2,3-dihydro-1-benzazepine-4-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

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

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

In toluene (15 ml), ethanol (1.5 ml) and water (1.5 ml) were suspended 7-bromo-1-(3-methoxybenzyl)-2,3-dihydro-1-benzazepine-4-carboxylic acid (320 mg), 4-butoxyethoxyphenyl borate (246 mg) and potassium carbonate (285 mg), and the suspension was stirred under argon atmosphere for 30 minutes. Then, to the suspension was added tetrakistriphenylphosphinepalladium (64 mg), and the mixture was heated at 100° C. for 8 hours under argon atmosphere. After allowing to cool, water was added to the mixture, 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=5:1) to give methyl 7-(4-butoxyethoxyphenyl)-1-(3-methoxybenzyl)-2,3-dihydro-1-benzazepine-4-carboxylic acid (207 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=5:1)

Quellen und Nachweise

ORD-Eintrag
ord-ce58d7828b984b25aa08ae3dc5802745
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06936602B1

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