Water → 3-(4-Methoxy-3-thiophen-3-ylbenzylidene)-1,3-dihydroindol-2-one

HRID 1860791

Reaktionsgleichung

Reaktionsgleichung von HRID 1860791
Br[C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][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+].[S:27]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28]1.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>[CH3:20][O:19][C:18]1[CH:17]=[CH:16][C:4]([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:3][C:2]=1[C:29]1[CH:30]=[CH:31][S:27][CH:28]=1

Komponenten

8

Edukt 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 581760Thiophene-3-boronic acidHCID 28031073-(3-Bromo-4-methoxybenzylidene)-1,3-dihydroindol-2-one

Produkt 1

HCID 537065203-(4-Methoxy-3-thiophen-3-ylbenzylidene)-1,3-dihydroindol-2-oneAusbeute 50 %

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-methoxybenzylidene)-1,3-dihydroindol-2-one (0.2 g, 0.61 mmol) in toluene (1 ml) and ethanol (1 ml), followed by addition of 2M aqueous sodium carbonate (1.2 ml, 2.4 mmol). To this mixture was added thiophene-3-boronic acid (0.09 g, 0.67 mmol) and the mixture was held at 100° C. in a sealed tube for 12 hours. The reaction was then poured into water (50 ml) and extracted with ethyl acetate (2×100 ml). The combined organic layers were washed with saturated aqueous sodium bicarbonate (50 ml) and brine (50 ml), dried over magnesium sulfate and concentrated. Chromatography (silica, methylene chloride then 30-40% ethyl acetate/hexanes) afforded 0.1 g (50%) of 3-(4-methoxy-3-thiophen-3-ylbenzylidene)-1,3-dihydroindol-2-one as a yellow solid.

Aufarbeitung

  1. extractionextracted with ethyl acetate (2×100 ml)
  2. washThe combined organic layers were washed with saturated aqueous sodium bicarbonate (50 ml) and brine (50 ml)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-b187382ae0ef4d0fa4da8c4fffe5ef2d
Quelldatensatz
uspto-grants-2003_03
Patentnummer
US06531502B1

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