반응 #77400

반응 방정식

sodium carbonate

pyridine-3-boronic acid propane diol

ethanol

6-bromo-2-oxindole

→

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

수율 42.0%

용매

ethyl acetate

toluene

반응 조건

후처리

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

실험 절차

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.

출처