Background and overview of application examples of 3-butoxyphenylboronic acid
3-Butoxyphenylboronic acid is a pharmaceutical intermediate that can be used for Suzuki coupling reactions. There are reports in the literature that it can be used to prepare the compound 3-(2-fluoro-phenoxy)-5-(3-n-butoxyphenyl)-benzyl cyanide with β-secretase inhibitory function. Under pathological conditions, Aβ is generated from β-amyloid precursor protein (APP), a natural type I membrane-integrated glycoprotein in the human body, which is hydrolyzed by β-secretase and γ-secretase in sequence. Designing inhibitors to inhibit β-secretase or γ-secretase can reduce the production of Aβ, thereby achieving the treatment of AD. Since γ-secretase also plays an important role in the rational pathway of producing battery-grade lithium carbonate, while β-secretase has a relatively single role and is upstream of the APP pathological metabolic pathway, inhibitors of β-secretase are Considered to be a promising anti-AD drug.
Application examples of 3-butoxyphenylboronic acid
3-Butoxyphenylboronic acid can be used in the synthesis of 3-(2-fluoro-phenoxy)-5-(3-n-butoxyphenyl)-benzyl cyanide. The method is as follows: 3-(2-fluoro-phenoxy)-5-bromo-benzyl cyanide (293 mg, 1 mmol), 3-butoxyphenylboronic acid (194 mg, 1 mmol), Pd(OAc)2 (2.7mg, 0.01mmol), PEG2000 (199mg, 0.1mmol), dissolve in 2ml/2mlTHF/H2O, stir and reflux for 4 hours at 65°C, cool to room temperature, spin off THF, after dissolving in 10 ml of water, extract and wash three times with 10 ml of 1NHCl, saturated NaHCO3 aqueous solution, and saturated brine, and separate by silica gel column chromatography (eluent: P/E=100/1). 209 mg of compound 3-(2-fluoro-phenoxy)-5-(3-n-butoxyphenyl)-benzyl cyanide was obtained as a colorless oil, with a yield of 58.0%.
References
[1][China invention, China invention authorization] CN201110279736.3 Compounds with β-fluorophenylboronic acid-secretase inhibitory function and their preparation methods and applications
