Uses
(2-Methoxypyridin-5-yl)boronic Acid Pinacol Ester is used in the design and synthesis of oxazolidinone antibacterial agents. As well, it is used in the synthesis of [3,2-b]pyridines.
Uses
2-Methoxypyridine-5-boronic acid pinacol ester is used in the design and synthesis of oxazolidinone antibacterial agents. As well, it is used in the synthesis of [3,2-b]pyridines.
Synthesis
Step 1: 5-bromo-2-methoxypyridine (55 g, 0.29 mol), pinacol ester of bisboronic acid (90 g, 0.35 mol), potassium acetate (57 g, 0.58 mol) and bis(triphenylphosphine)palladium(II) chloride (2.2 g, 3 mmol) were dissolved in anhydrous dioxane (500 mL) under nitrogen protection. The reaction mixture was heated and stirred at 108 °C overnight. Upon completion of the reaction, the mixture was concentrated and purified by column chromatography using hexane/ethyl acetate as eluent to afford pinacol ester of 6-methoxypyridine-3-boronic acid (58 g, 84% yield).
References
[1] Patent: US9249156, 2016, B2. Location in patent: Page/Page column 36
[2] Patent: WO2018/85342, 2018, A1. Location in patent: Page/Page column 26; 28
[3] Patent: WO2014/186035, 2014, A1. Location in patent: Page/Page column 151
[4] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 12, p. 2496 - 2500
[5] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 19, p. 6477 - 6485
