Preparation and application background and overview of 5-chloro-2-fluorophenylboronic acid
5-Chloro-2-fluorophenylboronic acid is a boric acid derivative. Boronic acid derivatives are widely used in organic synthesis for the formation of carbon-carbon bonds. In the Suzuki coupling, aryl halides and aryl or vinyl borates or boronic acids are coupled using Pd(PPh3)4. 5-Chloro-2-fluorobenzene boric acid can be prepared by reacting 2-bromo-4-chloro-1-fluorobenzene as raw material and triisopropyl borate.
Preparation and application of 5-chloro-2-fluorophenylboronic acid
To a solution of 2-bromo-4-chloro-1-fluorobenzene (5g, 0.0238mol) in anhydrous ether (30 mL) under nitrogen atmosphere at -70°C, 2M n-BuLi in n-hexane was added. Solution in alkane (13 mL, 0.0262 mol). The solution was stirred at the same temperature for 30 min, and then triisopropyl borate (4.93 g of boron trifluoride tetrahydrofuran complex, 0.0262 mol) was added dropwise to the solution. The resulting white slurry was stirred at -70°C for 30 min and then warmed to room temperature and stirred for 1 h. The reaction was monitored by TLC and H NMR. After the reaction was completed, the reaction mixture was hydrolyzed with 6N NaOH and stirred for 1 h. The reaction mixture was extracted with EtOAc. The organic layer was washed with brine and concentrated under reduced pressure to give a viscous compound, which was triturated with n-pentane and dried to give 5-chloro-2-fluorophenylboronic acid as an off-white solid.
Preparation and application of 5-chloro-2-fluorophenylboronic acid
5-Chloro-2-fluorophenylboronic acid can be used to prepare substituted pyrazole and pyrrole compounds with the following structures. This class of compounds can be used to treat hyperproliferative diseases. The hyperproliferative disorder is a hematopoietic cancer or a solid tumor.
References
[1] [China Invention, China Invention Authorization] CN201480075343.2 Compounds and Usage Methods [Disclosure]/Aminopyridine Compounds and Usage Methods [Authorization]
[2] CN201780085008.4 Methods of using substituted pyrazole and pyrrole sodium carbonate compounds and treating hyperproliferative diseases
