Preparation and application background and overview of 2-ethoxypyridine-5-boronic acid
2-Ethoxypyridine-5-boronic acid is a pharmaceutical intermediate that can be used to prepare BTK inhibitors. 2-Ethoxypyridine-5-boronic acid can be prepared from 2-ethoxypyridine and triisopropyl borate through a one-step reaction.
Preparation and application of 2-ethoxypyridine-5-boronic acid
Parry P R et al. reported that 2-ethoxypyridine-5-boronic acid can be prepared from 2-ethoxypyridine using butyllithium as a base at -78°C and reacting with triisopropyl borate. The yield is 61%.
Preparation and application of 2-ethoxypyridine-5-boronic acid
CN201280023444.6 reported that 2-ethoxypyridine-5-boronic acid can be used to prepare compound 1-[3-(6-tert-butyl-8-fluoro-1-oxo-1H-phthalazine-2- yl)-2-hydroxymethyl-phenyl]-6-(6-ethoxy-pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine-3-carboxamide. The compound is an inhibitor of BTK, a member of the Tec family of tyrosine kinases and shown to be a key regulator of early B cell formation as well as mature B cell activation and survival. Btk mutations in humans cause the condition X-linked agammaglobulinemia (XLA). These patients are immunocompromised and display impaired B cell maturation, reduced immunoglobulin and peripheral B cell levels, reduced T cell-independent immune responses, and attenuated calcium mobilization following BCR stimulation. Btk inhibitors can be used to treat pathological mast cell reactions such as allergies and asthma. Furthermore, monocytes from XLA patients, in which Btk activity is lacking, show reduced TNFα production upon stimulation. Therefore, TNFα-mediated inflammation can be modulated by small molecule Btk inhibitors. Furthermore, Btk has been reported to play a role in apoptosis, and thus Btk inhibitors would be effective in treating certain B-cell lymphomas and leukemias.
References
[1] Parry P R , Bryce M R , Tarbit B . New Shelf-Stable Halo- and Alkoxy-Substituted Pyridylboronic Acids and their Suzuki Cross-Coupling Reactions to Yield Heteroarylpyridines[J]. Cheminform, 2003, 2003(07): 1035-1038.
[Bismuth 2 borate] [Invented in China, authorized by China] CN201280023444.6 Tyrosine kinase inhibitor
