Category: 168823-76-5

Reference of 168823-76-5, 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.168823-76-5, name is 5-Bromo-2-(chloromethyl)pyridine, molecular formula is C6H5BrClN, molecular weight is 206.4676, as common compound, the synthetic route is as follows.

tert-Butyl (5S)-2-[(5-bromopyridin-2-yl)methyl]-3-oxo-2,3,5,6,7,8-hexahydro[1,2,4]triazolo[4,3-a]pyridine-5-carboxylate tert-Butyl (5S)-3-oxo-2,3,5,6,7,8-hexahydro[1,2,4]triazolo[4,3-a]pyridine-5-carboxylate (309 mg, 1.29 mmol) was initially charged in dichloromethane (7.3 ml). Caesium carbonate (1.05 g, 3.23 mmol) and 5-bromo-2-(chloromethyl)pyridine (347 mg, 1.68 mmol) were subsequently added. After stirring for 5 hours, the reaction mixture was admixed at room temperature with water and ethyl acetate. The organic phase was removed and the aqueous phase was extracted three times with ethyl acetate. The combined organic phases were washed with saturated aqueous sodium chloride solution, dried over sodium sulphate and filtered, and the filtrate was concentrated. The residue was purified via preparative HPLC (Chromatorex C18, 10 mum, 125 mm*30 mm; eluent: acetonitrile/water gradient). The product-containing fractions were concentrated under reduced pressure, and 580 mg (>100% of theory) of the title compound were obtained. LC-MS (Method 3): Rt=1.68 min; MS (ESIpos): m/z=409 [M+H]+

The chemical industry reduces the impact on the environment during synthesis 168823-76-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; BIBER, Nicole; BROCKSCHNIEDER, Damian; GERICKE, Kersten Matthias; KOeLLING, Florian; LUSTIG, Klemens; MEDING, Joerg; MEIER, Heinrich; NEUBAUER, Thomas; SCHAeFER, Martina; TIMMERMANN, Andreas; ZUBOV, Dmitry; TERJUNG, Carsten; LINDNER, Niels; BADOCK, Volker; MOOSMAYER, Dieter; MIYATAKE ONDOZABAL, Hideki; MOORE, Steven; SCHULZ, Alexander; (458 pag.)US2019/160048; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 168823-76-5, 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. 168823-76-5, name is 5-Bromo-2-(chloromethyl)pyridine. A new synthetic method of this compound is introduced below.

Example A50 Preparation of intermediate 50: (5-Bromo-pyridin-2-yl)-acetonitrile Potassium cyanide (0.489 g, 7.41 mmol) and potassium iodide (0.013 g, 0.079 mmol) were added to a stirred solution of 5-bromo-2-chloromethyl-pyridine (0.9 g, 3.70 mmol) (obtained by procedures similar to those described in, van den Heuvel, M. et al.; J. Org. Chem., 2004, 250) in a mixture of ethanol (6 ml) and water (2 ml). The mixture was stirred at 80 C. for 6 h., then diluted with dichloromethane and washed with a saturated solution of sodium hydrogen carbonate. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica; dichloromethane). The desired fractions were collected and concentrated in vacuo to yield intermediate 50 (0.498 g, 68%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,168823-76-5, 5-Bromo-2-(chloromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; Pastor-Fernandez, Joaquin; Bartolome-Nebreda, Jose Manuel; Macdonald, Gregor James; Conde-Ceide, Susana; Delgado-Gonzalez, Oscar; Vanhoof, Greta Constantia Peter; Van Gool, Michiel Luc Maria; Martin-Martin, Maria Luz; Alonso-de Diego, Sergio-Alvar; Swinney, Kelly Ann; Leys, Carina; Weerts, Johan Erwin Edmond; Wuyts, Stijn; US2011/269752; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem