Water → N-[3-(3'-acetylamino-6-methoxybiphenyl-3-ylmethylene)-2-oxo-2,3-dihydro-1H-indol-6-yl]-acetamide

HRID 24416Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 24416
Br[C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[CH:5]=[C:6]1[C:14]2[C:9](=[CH:10][C:11]([NH:15][C:16](=[O:18])[CH3:17])=[CH:12][CH:13]=2)[NH:8][C:7]1=[O:19].C(=O)([O-])[O-].[Na+].[Na+].[C:31]([NH:34][C:35]1[CH:36]=[C:37](B(O)O)[CH:38]=[CH:39][CH:40]=1)(=[O:33])[CH3:32].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>[C:31]([NH:34][C:35]1[CH:40]=[C:39]([C:2]2[C:22]([O:23][CH3:24])=[CH:21][CH:20]=[C:4]([CH:5]=[C:6]3[C:14]4[C:9](=[CH:10][C:11]([NH:15][C:16](=[O:18])[CH3:17])=[CH:12][CH:13]=4)[NH:8][C:7]3=[O:19])[CH:3]=2)[CH:38]=[CH:37][CH:36]=1)(=[O:33])[CH3:32]

Komponenten

8

Edukt 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 157274(3-Acetamidophenyl)boronic acidHCID 54460383N-[3-(3-bromo-4-methoxybenzylidene)-2-oxo-2,3-dihydro-1H-indol-6-yl]-acetamide

Produkt 1

HCID 69763391N-[3-(3'-acetylamino-6-methoxybiphenyl-3-ylmethylene)-2-oxo-2,3-dihydro-1H-indol-6-yl]-acetamideAusbeute 43,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

Tetrakis(triphenylphosphine)palladium(0) (0.01 g) was added to a solution of N-[3-(3-bromo-4-methoxybenzylidene)-2-oxo-2,3-dihydro-1H-indol-6-yl]-acetamide (0.14 g) in toluene (1 ml) and ethanol (1 ml) followed by addition of 2M aqueous sodium carbonate (0.72 ml). To this mixture was 3-acetylamino-phenylboronic acid (0.07 g), and the mixture was held at 100° C. in a sealed tube for 12 hours. The reaction mixture was added to 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, dichloromethane then 5-10% methanol/dichloromethane) afforded 0.07 g (43%) of N-[3-(3′-acetylamino-6-methoxybiphenyl-3-ylmethylene)-2-oxo-2,3-dihydro-1H-indol-6-yl]-acetamide as a yellow solid. About 26% isomer by 1HNMR.

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-082aadaa471d4039b25bf68b8860e1aa
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06855730B2

Notizen zur Reaktion

Wird geladen…