Preparation and application background and overview of 3-chloro-4-carboxylic acid methyl ester phenylboronic acid
3-Chloro-4-carboxylic acid methyl ester phenylboronic acid is an organic intermediate, which can be prepared by reacting 2-chloro-4-bromobenzoic acid methyl ester and pinacol diborate. Oxycarbonylphenylboronic acid pinacol ester is then oxidized with sodium periodate. 3-Chloro-4-carboxylic acid methyl ester phenylboronic acid can be used to perform Suzuki coupling reactions.
Preparation and application of 3-chloro-4-carboxylic acid methyl ester phenylboronic acid
To a solution of methyl 2-chloro-4-bromobenzoate (31.4 mmol) in dioxane (154 mL) was added pinacol diborate (8.6 g, 31.4 mmol), PdCl2(PPh3)2 (0.42mmol) and KOAc (94.2mmol), and the mixture was stirred at 100°C under nitrogen for 2-6 hours. The lithium carbonate mixture was diluted with EtOAc and water. The organic layer was separated, washed with brine, dried over MgSO4, and evaporated. The residue was purified by silica gel column chromatography (hexane/EtOAc 5/1) to give 3-chloro-4-methoxycarbonylphenylboronic acid pinacol ester. To a suspension of the above product (29.4mmol) in acetone (175mL) and water (175mL) were added NH4OAc (66.2mmol) and NaIO4 (14.2g , 66.4 mmol), and the mixture was stirred at room temperature for 15 hours. The solvent was evaporated and the residue was diluted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgSO4, and evaporated under reduced pressure to give the title compound as a white solid.
Preparation and application of 3-chloro-4-carboxylic acid methyl ester phenylboronic acid
3-Chloro-4-carboxylic acid methyl ester phenylboronic acid can be used to prepare sulfonamide compounds with the following structure. This class of compounds can be used as CaSR antagonists. This type of compound has an excellent effect of promoting PTH secretion, and it has been found that this compound is useful as an active ingredient in drugs for preventing and/or treating bone diseases such as osteoporosis, fractures, and hypoparathyroidism. of.
References
[1] From Journal of Medicinal Chemistry, 51(6), 1925-1944; 2008
[2] [China invention, China invention authorization] CN200980120805.7 Sulfonamide compounds and their uses
