تفاعل #928108

معادلة التفاعل

6-Bromo-oxindole

water

→

6-(Furan-2-yl)-oxindole

المذيبات

acetonitrile

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe reaction was cooled to room temperature
2. 2
   غسيلThe pad of celite was washed with EtOAc
3. 3
   أخرىseparated
4. 4
   غسيلThe aqueous layer was washed with EtOAc (2×20 mL each)
5. 5
   غسيلThe combined organic phases were washed with brine
6. 6
   تجفيفdried over sodium sulfate
7. 7
   أخرىThe volatiles ere removed in vacuo
8. 8
   أخرىThe resulting residue was triturated with diethyl ether
9. 9
   ترشيحthe solid was collected by filtration (0.13 g, 34%)

الإجراء التجريبي

6-Bromo-oxindole (0.40 g, 1.88 mmol), 2-tributyltinfuran (0.71 mL, 2.26 mmol), and tetraethylammonium chloride hydrate (0.31 g, 1.88 mmol) were combined and dissolved in acetonitrile (15 mL). The palladium catalyst, bistriphenylphosphinedichloropalladium (II) (0.66 g, 0.09 mmol) was added and the reaction was warmed to 85° C. under nitrogen for 20 hours. The reaction was cooled to room temperature and diluted with water (15 mL) before passing the mixture through celite. The pad of celite was washed with EtOAc and the filtrates were combined and separated. The aqueous layer was washed with EtOAc (2×20 mL each). The combined organic phases were washed with brine and dried over sodium sulfate. The volatiles ere removed in vacuo. The resulting residue was triturated with diethyl ether and the solid was collected by filtration (0.13 g, 34%). 1H NMR 300 MHz (DMSO-d6) δ10.5 (s, 1H); 7.75 (s, 1H); 7.30 (m, 2H); 7.11 (s, 1H); 6.91 (m, 1H); 6.60 (m, 1H); 3.52 (s, 2H).

المصدر