Réaction #7108

Équation de réaction

tris-iso-propylborate

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

sodium hydride

HCl

butyl lithium

→

subtitled compound

Rendement 64.0%

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

Rendement 64.0%

Solvants

THF

Conditions de réaction

Traitement

1. 1
   workup.WAITAfter 30 minutes
2. 2
   Autrewas slowly brought to room temperature
3. 3
   Extractionextracted with EtOAc (×3)
4. 4
   AutreThe organic layers were collected
5. 5
   Lavagewashed with 1N HCl, water
6. 6
   Séchagedried (MgSO4)
7. 7
   Autreevaporated

Mode opératoire

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.

Source