Application
5-Bromo-2-ethoxypyridine-4-boronic acid is an organic intermediate that can be used in coupling reactions such as Suzuki, and is mainly used in laboratory research and development processes and chemical and pharmaceutical synthesis processes.
Synthesis
LDA (2.0 M in heptane-THF-ethylbenzene, 2.0 mL, 4.0 mmol) was added dropwise to a solution of 5-bromo-2-methoxypyridine (9) (727 mg, 3.9 mmol) in anhydrous THF (10 mL) at -78 C. The reaction mixture was stirred at -78 C for 1 h, then TIPB (1.5 g, 7.8 mmol) was added dropwise. The mixture was stirred at -78 C for 1 h, then quenched with H2O (10 mL) and allowed to warm to 20 C overnight. Post-treatment of the reaction solution (the aqueous layer was then acidified to pH 4 with 48% aqueous HBr to precipitate) gave the product 3-bromo-6-methoxy-4-pyridinylboronic acid.
5-Bromo-2-ethoxyarsenyl-4-boronic acid was synthesized with reference to the method described above from the following materials: a solution of 5-bromo-2-ethoxypyridine (10) (261 mg, 1.3 mmol), THF (10 mL), and LDA (2.0 M heptane-THF-ethylbenzene, 0.8 mL, 1.5 mmol). The product was a white solid (74 mg, 23%).
