반응 #928108

반응 방정식

6-Bromo-oxindole

water

→

6-(Furan-2-yl)-oxindole

용매

acetonitrile

반응 조건

후처리

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

실험 절차

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).

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