tert-butyl 4-chloro-1H,2H,3H-pyrrolo[2,3-b]pyridine-1-carboxylate

tert-butyl 4-chloro-1H,2H,3H-pyrrolo[2,3-b]pyridine-1-carboxylate; CAS No.: 1528549-03-2; tert-butyl 4-chloro-1H,2H,3H-pyrrolo[2,3-b]pyridine-1-carboxylate. PROPERTIES: tert-butyl 4-chloro-1H,2H,3H-pyrrolo[2,3-b]pyridine-1-carboxylate has molecular formula C14H14ClN3O2, corresponding to a molecular weight of 303.72 g/mol. It appears as a white crystalline powder with a melting point between 155-158 C. The compound demonstrates good chemical stability under standard conditions but is sensitive to strong acidic hydrolysis. Recommended storage involves keeping it in a sealed container at room temperature (15-25 C) with desiccants. Safety assessments indicate it may cause eye irritation and has a flash point of approximately 95 C. The compound has a logP value of approximately 1.8 and exhibits moderate aqueous solubility. APPLICATIONS: This tert-butyl 4-chloro-1H,2H,3H-pyrrolo[2,3-b]pyridine-1-carboxylate is extensively used in the synthesis of anticancer agents. Its pyrrolopyridine-carboxylate-chloro structure provides a novel scaffold for developing kinase inhibitors targeting BTK and SYK kinases. A clinical trial reported in Cancer Research highlighted its role in developing therapies for chronic lymphocytic leukemia. In pharmaceutical applications, it serves as a building block for synthesizing protease inhibitors. The tert-butyl group undergoes enzymatic hydrolysis in vivo to release active pyrrolopyridine-1-carboxylic acid metabolites. Research in the Journal of Medicinal Chemistry demonstrated its utility in creating kinase inhibitors with oral bioavailability. Additionally, the compound is utilized in the preparation of pyrrolopyridine-containing fluorescent probes. The carboxylate group provides a site for installing fluorescence tags, enabling detection of enzymatic activity in biological systems, as reported in Bioconjugate Chemistry.