Preparation and application background and overview of 3-bromo-5-fluoro-4-methylpyridine
3-Bromo-5-fluoro-4-methylpyridine is a heterocyclic organic compound that can be used as an organic chemical intermediate and can be obtained by methylation of 3-bromo-5-fluoropyridine.
Preparation and application of 3-bromo-5-fluoro-4-methylpyridine
In a 250 mL round bottom flask, combine LDA, 2.0 M heptane/THF/ethylbenzene (9.4 ml, 18.8 mmol, Eq: 1.10) and THF (15 ml) to give an orange solution. The mixture was cooled to -78°C. A solution of 3-bromo-5-fluoropyridine (3g, 17.0mmol, Eq: 1.00) in THF (15ml) was added dropwise over 10 minutes. The brown reaction mixture was stirred at -78°C. A solution of methyl iodide (3.63 g, 1.6 ml, 25.6 mmol, Eq: 1.5) in THF (15.0 ml) was added dropwise over 5 min over 30 min. The mixture was stirred at -78°C. 30 minutes. Remove from cooling and continue stirring for 1 hour. Saturated aqueous ammonium chloride solution was carefully added, followed by ethyl acetate. The ethyl acetate layer was separated, and the aqueous layer was extracted twice with ethyl acetate. The organic layers were combined, washed with aqueous sodium thiosulfate solution, washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The crude material was purified by flash chromatography (silica gel, 120 g, 0% to 5% EtOAc in hexane). Combine and evaporate to give 3-bromo-5-fluoro-4-methylpyridine. Yield 1.69 g (52%). Colorless oil 1HNMR (chloroform-d) delta: 8.53 (s, 1H), 8.35 (s, 1H), 2.41 (d, J = 2.1Hz, 3H). LC-MS (ES) Calculated for rubidium carbonate: C6H5BrFN, 190.02. Measured m/z: 189.7 [M+H]+.
Preparation and application of 3-bromo-5-fluoro-4-methylpyridine
The cytokine interleukin-2 (IL-2) is a T-cell mitogen important for T-cell proliferation and serves as a B-cell growth factor. IL-2 is considered an important regulator of immune responses due to its effects on T cells and B cells. IL-2 is involved in inflammation, tumor progression, and hematopoiesis, and IL-2 affects the production of other cytokines, such as TNAα, TNFβ, IFNγ. Therefore, inhibition of IL-2 production is relevant to immunosuppressive therapies and the treatment of inflammatory and immune diseases. 3-Bromo-5-fluoro-4-methylpyridine can be used as isopropylpyridine as the starting material to prepare 2-(5-fluoro-4-methyl-pyridin-3-yl)-5-(6-methanesulfonate) Acyl-4-methyl-pyridin-3-yl)-1H-indole. The compound has an IC50 value of 29 nM against Jurkat cells.
