Réaction #52665

Équation de réaction

water

3-(3-Bromo-4-methoxy-benzylidene)-1,3-dihydroindol-2-one

sodium carbonate

3-acetamidophenylboronic acid

→

N-[2′-methoxy-5′-(2-oxo-1,2-dihydroindol-3-ylidenemethyl)-biphenyl-3-yl]-acetamide

Rendement 22.0%

Solvants

toluene

ethanol

Conditions de réaction

Traitement

1. 1
   Extractionextracted with ethyl acetate (2×100 ml)
2. 2
   LavageThe combined organic layers were washed with saturated aqueous sodium bicarbonate (50 ml) and brine (50 ml)
3. 3
   SéchageThe organic layer was dried over magnesium sulfate
4. 4
   Concentrationconcentrated
5. 5
   AutreChromatography (silica, 30-40% ethyl acetate/hexanes),afforded a waxy solid that was triturated with diethyl ether/hexanes
6. 6
   Autredried

Mode opératoire

Tetrakis(triphenylphosphine)palladium(0) (0.02 g, 0.02 mmol) was added to a solution of 3-(3-Bromo-4-methoxy-benzylidene)-1,3-dihydroindol-2-one (0.2 g, 0.61 mmol) in toluene (1 ml) and ethanol (2 ml), followed by addition of 2M aqueous sodium carbonate (1.2 ml, 2.4 mmol). To this mixture was added 3-acetamidophenylboronic acid (0.12 g, 0.67 mmol), and the mixture was heated to 100° C. in a sealed tube and held there 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). The organic layer was dried over magnesium sulfate and concentrated. Chromatography (silica, 30-40% ethyl acetate/hexanes),afforded a waxy solid that was triturated with diethyl ether/hexanes and then dried to afford 0.05 g (22%) of N-[2′-methoxy-5′-(2-oxo-1,2-dihydroindol-3-ylidenemethyl)-biphenyl-3-yl]-acetamide as a reddish orange solid.

Source