Adding a certain compound to certain chemical reactions, such as: 942947-94-6, 5-Bromo-4-chloropyridin-2-amine, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, 942947-94-6, blongs to pyridine-derivatives compound. Computed Properties of C5H4BrClN2
Synthesis of 4-chloro-5-(4,4,5,5-tetramethyl(l,3,2-dioxaborolan-2-yl))-2- pyridylamine[00100] To a dry 500-mL flask was added 5-bromo-4-chloro 2-pyridylamine (7.3 g, 35.8 mmol), potassium acetate (10.3 g, 105 mmol), 4,4,5,5-tetramethyl-2-(4,4,5,5- tetramethyl-l ,3,2-dioxaborolan-2-yl)-l,3,2-dioxaborolane (10.1 g, 39.8 mmol) and dioxane (150 mL). Argon was bubbled through the solution for 15 minutes, at which time l,l’-bis(diphenylphosphino)ferrocene palladium(II) chloride dichloromethane adduct (0.85 g, 1.04 mmol) was added. The reaction was refluxed in a 1 15 C oil bath for 6 hours under argon. After cooling to room temperature, the dioxane was removed in vacuo. EtOAc (500 mL) was then added and the resulting slurry was sonicated and filtered. Additional EtOAc (500 mL) was used to wash the solid. The combined organic extracts were concentrated and the crude material was purified by Si02 chromatography (EtOAc as eluent). Upon removal of solvent, 3: 1 hexanes/CH2Cl2 was added (100 mL). After soni cation, the resulting solid was filtered and concentrated in vacuo yielding 2.8 g of a white solid. By ¾ NMR the material was a 10: 1 mixture of boronate ester and 2-amino-4-chloropyridine byproduct. The material was used as is in subsequent Suzuki reactions. LCMS (m/z):173 (MH+ of boronic acid, deriving from in situ product hydrolysis on LC). ¾ NMR (CDCI3): delta 8.36 (s, 1H), 6.46 (s, 1H), 4.70 (bs, 2H), 1.38 (s, 12H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,942947-94-6, its application will become more common.
Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; ZHAO, Jean J.; WANG, Qi; WO2012/109423; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem