反应 #939690

反应方程式

tris-iso-propylborate

5-bromo-spiro[cyclopentane-1,3′-[3H]indol]-2′(1′H)-one

sodium hydride

HCl

butyl lithium

→

subtitled compound

收率 64.0%

(Spiro[cyclopentane-1,3′-[3H]indol]-2′(1′H)-one-5-yl) boronic acid

收率 64.0%

溶剂

THF

反应条件

后处理

1. 1
   workup.WAITAfter 30 minutes
2. 2
   其他was slowly brought to room temperature
3. 3
   萃取extracted with EtOAc (×3)
4. 4
   其他The organic layers were collected
5. 5
   洗涤washed with 1N HCl, water
6. 6
   干燥dried (MgSO4)
7. 7
   其他evaporated

实验过程

To a solution of 5-bromo-spiro[cyclopentane-1,3′-[3H]indol]-2′(1′H)-one (13.1 g, 53 mmol) in anhydrous THF (300 cm3) under N2, was added sodium hydride (60% in mineral oil, 2.1 g, 53 mmol). After 30 minutes, the reaction mixture was cooled to −78° C. and butyl lithium (2.5 M in hexanes, 22 cm3, 53 mmol) was added slowly. After 30 minutes, tris-iso-propylborate (34 cm3, 146 mmol) was added, and the reaction mixture was slowly brought to room temperature, and stirred for 14 hours. The reaction mixture was poured into 1N HCl and extracted with EtOAc (×3). The organic layers were collected and washed with 1N HCl, water, dried (MgSO4) and evaporated to give the subtitled compound (7.8 g, 64%) as a tan solid which was used without further purification. 1H NMR (DMSO-d6) δ 10.3 (s, 1H), 7.9 (s, 1H), 7.7-7.6 (m, 2H), 6.8 (d, 1H, J=7.7 Hz), 3.4 (s, 1H), 2.0-1.7 (m, 8H); MS (FI-POS) m/z @ 231.

来源