反応 #928103

反応方程式

5-Bromo-7-azaoxindole

EtOAc

→

solid

収率 36.0%

5-(Furan-2-yl)-7-aza-oxindole

収率 36.0%

溶媒

KF

acetonitrile

反応条件

後処理

1. 1
   温度The reaction was cooled to room temperature
2. 2
   その他the layers separated
3. 3
   その他the volatiles removed in vacuo
4. 4
   その他The resulting residue was triturated with diethyl ether
5. 5
   ろ過the solids were collected by filtration

実験手順

5-Bromo-7-azaoxindole (0.75 g, 3.52 mmol), 2-tributyltinfuran (1.26 g, 3.52 mmol), tetraethylammonium chloride hydrate (1.94 g, 10.6 mmol) were combined and dissolved in acetonitrile (10 mL) at room temperature under an atmosphere of nitrogen. Bistriphenylphosphine dichloropalladium (II) (0.25 g, 0.35 mmol) was added and the reaction was warmed to 85° C. for 16 hours. The reaction was cooled to room temperature and diluted with aqueous KF (10%, 60 mL). This was stirred for 20 minutes and then diluted with EtOAc (60 mL). The biphasic system was passed through celite, the layers separated, and the volatiles removed in vacuo. The resulting residue was triturated with diethyl ether and the solids were collected by filtration to afford a light yelow solid (0.28 g, 36% yield). 1H NMR 300 MHz (DMSO-d6) δ11.18 (bs, 1H); 8.45 (s, 1H); 7.92 (s, 1H); 7.79 (s, 1H); 6.95 (d, 1H); 6.60 (d, 1H); 3.64 (s, 2H). APCI m/z 201 (M+1).

出典