As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 186413-75-2, name is 3-Bromo-6-chloro-2-methyl-5-nitropyridine, molecular formula is C6H4BrClN2O2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. SDS of cas: 186413-75-2
To a stirred solution of 3-bromo-6-chloro-2-methyl-5-nitropyridine (2.00 g, 7.95 mmol) in tetrahydrofuran (16 mL) at -78 C. was added (E)-but-2-en-2-ylmagnesium bromide (0.5M in THF) (55.7 mL, 27.8 mmol). The reaction mixture was allowed to warm to ?35 C. over 30 min. and was then quenched with a saturated aqueous solution of ammonium chloride. The mixture was diluted with ethyl acetate, washed with a saturated aqueous solution of ammonium chloride, washed with brine, and dried over anhydrous sodium sulfate. The organic layer was collected, and the aqueous layers were sequentially washed extracted with ethyl acetate (2*). The combined organic layers were dried over anhydrous sodium sulfate, and the resulting residue was purified by ISCO flash silica gel chromatography (24 g column; gradient: 0%-100 ethyl acetate in hexane) to give 4-bromo-7-chloro-2,3,5-trimethyl-1H-pyaolo[2,3-c]pyridine (0.402 g, 1.47 mmol, 19% yield) as a yellow solid. The product had a UPLC ret. time=1.14 min. -Column: PHENOMENEX Kinetex C18 2.1×50 mm (1.5 min. gradient); Solvent A=10% MeCN, 90% H2O, 0.1% TFA; Solvent B=90% MeCN, 10% H2O, 0.1% TFA. LC/MS M+1=273.2 and 275.2.
With the rapid development of chemical substances, we look forward to future research findings about 186413-75-2.
Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; Liu, Qingjie; Watterson, Scott Hunter; Batt, Douglas G.; Ahmad, Saleem; Beaudoin Bertrand, Myra; Gong, Hua; Guo, Weiwei; Macor, John E.; Ngu, Khehyong; Tebben, Andrew J.; Tino, Joseph A.; (177 pag.)US2016/115126; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem