تفاعل #77400

معادلة التفاعل

sodium carbonate

pyridine-3-boronic acid propane diol

ethanol

6-bromo-2-oxindole

→

6-pyridin-3-yl-1,3-dihydro-indol-2-one

المردود 42.0%

المذيبات

ethyl acetate

toluene

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added
2. 2
   أخرىThe cooled reaction
3. 3
   غسيلwashed with saturated aqueous sodium bicarbonate (200 mL), water (200 mL) and brine (200 mL)
4. 4
   تجفيفThe organic layer was dried with magnesium sulfate
5. 5
   تركيزconcentrated
6. 6
   أخرىto afford a brown solid
7. 7
   أخرىThe residue was triturated with methylene chloride/diethyl ether

الإجراء التجريبي

To a solution of 6-bromo-2-oxindole (4 g, 26.3 mmol) dissolved in 60 mL of toluene and 60 mL of ethanol with stirring and a little heating tetrakis(triphenyl-phosphine)palladium(0) (2.3 g, 1.9 mmol) was added followed by a 2M aqueous solution of sodium carbonate (50 mL, 100 mmol) and pyridine-3-boronic acid propane diol (5 g, 30.7 mmol). The mixture was heated in a 100° C. oil bath for 12 hours. The cooled reaction was diluted with ethyl acetate (500 mL), washed with saturated aqueous sodium bicarbonate (200 mL), water (200 mL) and brine (200 mL). The organic layer was dried with magnesium sulfate and concentrated to afford a brown solid. The residue was triturated with methylene chloride/diethyl ether to give 2.32 g (42%) of 6-pyridin-3-yl-1,3-dihydro-indol-2-one as a brown solid.

المصدر