Water → 3-(3'-Ethoxy-4,5-dimethoxybiphenyl-2-ylmethylene)-1,3-dihydroindol-2-one

HRID 1860810

Reaktionsgleichung

Reaktionsgleichung von HRID 1860810
Br[C:2]1[CH:3]=[C:4]([CH:16]=[C:17]([O:21][CH3:22])[C:18]=1[O:19][CH3:20])[CH:5]=[C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][C:7]1=[O:15].C(=O)([O-])[O-].[Na+].[Na+].[CH2:29]([O:31][C:32]1[CH:33]=[C:34](B(O)O)[CH:35]=[CH:36][CH:37]=1)[CH3:30].O>C1(C)C=CC=CC=1.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>[CH2:29]([O:31][C:32]1[CH:37]=[C:36]([C:3]2[CH:2]=[C:18]([O:19][CH3:20])[C:17]([O:21][CH3:22])=[CH:16][C:4]=2[CH:5]=[C:6]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[NH:8][C:7]2=[O:15])[CH:35]=[CH:34][CH:33]=1)[CH3:30]

Komponenten

8

Edukt 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27739203-Ethoxybenzeneboronic acidHCID 545646043-(3-Bromo-4,5-dimethoxybenzylidene)-1,3-dihydroindol-2-one

Produkt 1

HCID 544706843-(3'-Ethoxy-4,5-dimethoxybiphenyl-2-ylmethylene)-1,3-dihydroindol-2-oneAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

Tetrakis(triphenylphosphine)palladium(0) (0.02 g, 0.02 mmol) was added to a solution of 3-(3-bromo-4,5-dimethoxybenzylidene)-1,3-dihydroindol-2-one (0.2 g, 0.56 mmol) in toluene (1 ml) and ethanol (1 ml), followed by addition of 2M aqueous sodium carbonate (1 ml, 2 mmol). To this mixture was added 3-ethoxyphenylboronic acid (0.1 g, 0.62 mmol) and the mixture was held at 100° C. in a sealed tube for 12 hours. The reaction mixture was then added to water (40 ml) and extracted with ethyl acetate (2×75 ml) The combined organic layers were washed with saturated aqueous sodium bicarbonate (50 ml) and brine (50 ml), dried over magnesium sulfate and concentrated. The resulting solid was triturated with methylene chloride/hexanes to afford 0.14 g (64%) of 3-(3′-ethoxy-4,5-dimethoxybiphenyl-2-ylmethylene)-1,3-dihydroindol-2-one as a yellow/orange solid.

Aufarbeitung

  1. extractionextracted with ethyl acetate (2×75 ml) The combined organic layers
  2. washwere washed with saturated aqueous sodium bicarbonate (50 ml) and brine (50 ml)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe resulting solid was triturated with methylene chloride/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-7eb7972120584f6399edeccc3f089ff8
Quelldatensatz
uspto-grants-2003_03
Patentnummer
US06531502B1

Verknüpfte Notizen

Wird geladen…