Reacción #52671

Ecuación de reacción

thiophene-3-boronic acid

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

water

sodium carbonate

→

3-(4-methoxy-3-thiophen-3-ylbenzylidene)-1,3-dihydroindol-2-one

Rendimiento 50.0%

Disolventes

toluene

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted with ethyl acetate (2×100 ml)
2. 2
   LavadoThe combined organic layers were washed with saturated aqueous sodium bicarbonate (50 ml) and brine (50 ml)
3. 3
   Secadodried over magnesium sulfate
4. 4
   Concentraciónconcentrated

Procedimiento

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 (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.

Fuente