With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.1211517-76-8, name is 3-Bromo-5-fluoro-4-methylpyridine, molecular formula is C6H5BrFN, molecular weight is 190.013, as common compound, the synthetic route is as follows.Formula: C6H5BrFN
Step D 3-fluoro-4-methyl-5-f4 A5,5-tetramethyl-l ,3,2-dioxaborolan-2-yl) yridme3-bromo-5-fluoro-4-methylpyridine (9.25 mmol, 2.93 g) bis(pinacolato)diboron (11.10 mmol, 2.82 g) l, -bis(diphenylphosphino)ferrocenedichloropalladium(II) (0.463 mmol, 0.335 g) and potassium acetate (18.50 mmol, 1.816 g) were combined in dioxane (37.0 mL) and heated to 80 C for 24 hours, under nitrogen. The reaction was allowed to cool to room temperature, EtOAc (400ml) added and the mixture filtered through CELITE and washed with 1 :1 saturated sodium bicarbonate solution / water (2 x 200ml) and brine (100ml). Organics were dried over sodium sulphate and solvent evaporated under reduced pressure to yield crude product as a brown oil. Purification by silica chromatography eluting with 25 to 50% EtOAc / heptane afforded 3-fluoro-4-methyl-5-(4J4,5,5-tetramethyl-l.3,2-dioxaborolan-2-yl)pyridine. 1H NMR (CDC13)5: 8.68 (s, IH), 8.39 (s, 1H), 2.48 (s, 3H), 1.38 (s, 12H).
At the same time, in my other blogs, there are other synthetic methods of this type of compound,1211517-76-8, 3-Bromo-5-fluoro-4-methylpyridine, and friends who are interested can also refer to it.
Reference:
Patent; MERCK SHARP & DOHME CORP.; HOYT, Scott, B.; PARK, Min, K.; LONDON, Clare; XIONG, Yusheng; BENNETT, D., Jonathan; CAI, Jaiqiang; RATCLIFFE, Paul; COOKE, Andrew; CARSWELL, Emma; MACLEAN, John; SAXENA, Rohit; KULKARNI, Bheemashankar, A.; GUPTA, Archana; WO2012/12478; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem