Extracurricular laboratory: Synthetic route of 2-Bromo-3-chloro-5-(trifluoromethyl)pyridine

At the same time, in my other blogs, there are other synthetic methods of this type of compound,75806-84-7, 2-Bromo-3-chloro-5-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Related Products of 75806-84-7, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 75806-84-7, name is 2-Bromo-3-chloro-5-(trifluoromethyl)pyridine. A new synthetic method of this compound is introduced below.

Example 63 10-Chloro-1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-7-(1-ethylpropyl)-2,3,4,5-tetrahydro-1H-[1,3]diazepino[1,2-a]benzimidazole A mixture of 10-chloro-7-(1-ethylpropyl)-2,3,4,5-tetrahydro-1H-[1,3]diazepino[1,2-a]benzimidazole (Reference Example 72; 150 mg, 0.51 mmol), 2-bromo-3-chloro-5-(trifluoromethyl)pyridine (401 mg, 1.54 mmol), copper(I) iodide (97 mg, 0.51 mmol), 2,2′-bipyridyl (159 mg, 1.02 mmol) and cesium carbonate (333 mg, 1.02 mmol) in 1-methyl-2-pyrrolidinone (2.0 mL) was stirred at 150 C. for 16 hr. The mixture was diluted with ethyl acetate, filtered through a pad of celite, washed with 2N hydrochloric acid, water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluding with a 5-20% ethyl acetate/n-hexane gradient mixture. The filtrate was concentrated in vacuo to give a residue, which was purified by preparative HPLC to give a solid, which was recrystallized from n-hexane/ethyl acetate to give the title compound (104 mg, 0.221 mmol, 43%) as a colorless solid. mp 108-110 C. 1H NMR (CDCl3) delta 0.87 (t, J=7.3 Hz, 6H), 1.67-2.13 (m, 8H), 3.02-3.19 (m, 1H), 4.18-4.28 (m, 2H), 4.48-4.56 (m, 2H), 6.99 (d, J=8.3 Hz, 1H), 7.21 (d, J=8.3 Hz, 1H), 7.73-7.85 (m, 1H), 8.43-8.57 (m, 1H). MS Calcd.: 470; Found: 471 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,75806-84-7, 2-Bromo-3-chloro-5-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; US2009/186879; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem