New downstream synthetic route of 58530-53-3

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 58530-53-3, 2,4-Dibromopyridine, other downstream synthetic routes, hurry up and to see.

Electric Literature of 58530-53-3, Adding some certain compound to certain chemical reactions, such as: 58530-53-3, name is 2,4-Dibromopyridine,molecular formula is C5H3Br2N, 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 58530-53-3.

In a 1L round-bottom flask are combined 2,4-dibromopyridine (20.0 g, 84.6 mmol), copper iodide (3.22 g, 16.9 mmol), 1,10-phenanthroline (6.10 g, 33.8 mmol), cesium carbonate (110 g, 338 mmol), Celite (16 g) and p-xylene (170 mL). To the resulting slurry is added 2-bromo-4-methylaniline (10.6 mL, 84.6 mmol) and nitrogen is bubbled through the vigorously stirred mixture for 10 minutes. The flask is fitted with a reflux condenser and the system is heated at 135C for 24 hours. The reaction mixture is cooled to room temperature and filtered. The filter cake is rinsed with methylene chloride and ethyl acetate and the combined organic filtrates are concentrated under reduced pressure over silica gel. The crude reaction product is purified by chromatography on silica gel using a gradient of 0 to 10% ethyl acetate in methylene chloride. The resulting brown solid is slurried in methylene chloride and triturated using hexanes, then isolated by filtration to provide the title compound (6.52 g, 25.0 mmol, 30% yield) as a shiny yellow solid: 1H NMR (400.13 MHz, DMSO-d6 with TFA-d) ppm: 9.40 (dd, J=0.9, 7.2 Hz, 1H), 8.45 (dd, J=0.7, 1.8 Hz, 1H), 8.42 (bs, 1H), 7.86 (dd, J=2.1, 7.3 Hz, 1H), 7.83 (d, J=8.4 Hz, 1H), 7.64 (dd, J=0.9, 8.4 Hz, 1H), 2.57 (s, 3H); 13C NMR (100.62 MHz, DMSO-d6 with TFA-d) ppm 142.6, 134.6, 131.9, 130.8, 129.9, 129.4, 127.0, 119.7, 115.0, 113.8, 113.4, 21.1; HRMS (m/z): found: 261.0013 (M+H), calcd for C12H10N2Br: 261.0027, Err=-5.4 ppm.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 58530-53-3, 2,4-Dibromopyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ELI LILLY AND COMPANY; ATTARDO, Giorgio; HORCHLER, Carey; XIONG, Hui; (53 pag.)WO2017/83198; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem