反応 #939690

反応方程式

tris-iso-propylborate

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

sodium hydride

HCl

butyl lithium

→

subtitled compound

収率 64.0%

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

収率 64.0%

溶媒

THF

反応条件

後処理

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

実験手順

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.

出典