Month: April 2022

Electric Literature of 79491-46-6 ,Some common heterocyclic compound, 79491-46-6, molecular formula is C6H4Br2N2O3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

E4. 2-Bromo-5,6-dimethoxy-3-nitropyridine 20 g of 2,6-dibromo-3-methoxy-5-nitropyridine (example E3) are dissolved in 550 ml of anhydrous methanol at 30-40 C. 4.6 g sodium methoxide dissolved in 30 ml anhydrous methanol is added to this solution. The reaction mixture is stirred for one hour at room temperature, poured into 700 ml of water and stored in the refrigerator overnight. The precipitate is filtered, washed with ice cold water and dried under vacuum to yield the title compound. 1H NMR (400 MHz, CDCl3): delta = 3.95 (s, 3H), 4.12 (s, 3H), 7.69 (s, 1 H). 13C NMR (100 MHz, CDCl3): delta = 55.68, 56.73, 115.33, 121.89, 143.18, 155.10.

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. 79491-46-6, 2,6-Dibromo-3-methoxy-5-nitropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; 4SC AG; EP2017277; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 1211518-35-2, name is Methyl 6-chloro-5-(trifluoromethyl)picolinate. A new synthetic method of this compound is introduced below., Quality Control of Methyl 6-chloro-5-(trifluoromethyl)picolinate

d) 6-Cyclopropylmethoxy-5-trifluoromethyl-pyridine-2-carboxylic acid Sodium hydride (1.1 g, 31.4 mmol) was added in portions to cyclopropylmethanol (20 mL) and the mixture was stirred at room temperature for 0.5 hours. 6-Chloro-5-(trifluoromethyl)-pyridine-2-carboxylic acid methyl ester (1.5 g, 6.3 mmol) was added and the resulting solution was stirred at 80 C for 1 h. Water (20 mL) was added; the solution was acidified with 6 N hydrochloric acid and then concentrated to give a residue which was partitioned between water (30 mL) and ethyl acetate (20 mL). The aqueous solution was extracted with ethyl acetate (2 x 20 mL) and the combined organic phase was washedwith brine (20 mL), dried over anhydrous sodium sulfate, filtered and concentrated to give the crude target compound. The crude target compound was purified by column chromatography (silica gel, 10 g, 15% ethyl acetate in petroleum ether) to give the title compound (1.4 g, 85%) as white solid; MS (El): mle = 262.0 [MH?i.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 1211518-35-2, Methyl 6-chloro-5-(trifluoromethyl)picolinate.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; FREI, Beat; GOBBI, Luca; GRETHER, Uwe; KIMBARA, Atsushi; NETTEKOVEN, Matthias; ROEVER, Stephan; ROGERS-EVANS, Mark; SCHULZ-GASCH, Tanja; WO2014/86705; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 73583-41-2 ,Some common heterocyclic compound, 73583-41-2, molecular formula is C5H3BrClN, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

General procedure: Toluene/tert-butanol(6 mL, v/v, 5:1) was added to the mixture of 4-piperidone ketal(1.0 mmol, 1.0 equiv), aryl bromide 15af. (1.1 mmol, 1.1 equiv),sodium tert-butoxide (1.0 mmol, 1.0 equiv), palladium diacetate(0.05 mmol, 0.05 equiv), and X-Phos (0.05 mmol, 0.05 equiv), andthe mixture was stirred in a microwave reactor under argon for15 min at 160 C. After the reaction vials were cooled to roomtemperature and filtered over celite, they were rinsed well withethyl acetate. The filtrate was subsequently evaporated underreduced pressure to obtain the compounds 16a-f.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,73583-41-2, its application will become more common.

Reference:
Article; Wang, Zhengyu; Shi, Xiaofan; Zhang, Huan; Yu, Liang; Cheng, Yanhua; Zhang, Hefeng; Zhang, Huibin; Zhou, Jinpei; Chen, Jing; Shen, Xu; Duan, Wenhu; European Journal of Medicinal Chemistry; vol. 139; (2017); p. 128 – 152;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 358780-14-0, Adding some certain compound to certain chemical reactions, such as: 358780-14-0, name is 1-(6-(Trifluoromethyl)pyridin-3-yl)ethanone,molecular formula is C8H6F3NO, 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 358780-14-0.

In methanol (30.0 mL), 10.3 mmol l-[6-(Trifluoromethyl)-3- pyridinyl]ethanone is dissolved. Sodium borohydride (584 mg, 15.4 mmol) is added and the mixture is stirred at 0C for 30 minutes. The solvent is evaporated under reduced pressure and water is added. Extraction with ethyl acetate, washing with saturated brine and drying over anhydrous sodium sulfate is performed. After filtration, the solvent in the filtrate is evaporated under reduced pressure.

According to the analysis of related databases, 358780-14-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SOLVAY SA; BRAUN, Max Josef; (21 pag.)WO2017/198812; (2017); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1000025-07-9, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 1000025-07-9, name is Vadadustat. This compound has unique chemical properties. The synthetic route is as follows.

Vadadustat (4.0g), L-Proline (2.85g) and acetone (60mL) were charged in a RBF at 25±5C and the contents were heated to 60-65C and stirred for 60 minutes at 60-65C. The reaction mass was slowly cooled to 25±5C and maintained under stirring at 25±5C for 16 hours. The product obtained was filtered, washed with acetone (8 mL) and dried under vacuum for 16 hours at 40C. The solid obtained was identified as 1 :2 co-crystal of Vadadustat L-Proline. Yield: 6.1 g

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 1000025-07-9, Vadadustat.

Reference:
Patent; MYLAN LABORATORIES LIMITED; JETTI, Ramakoteswara Rao; PILLI, Narasimha Murty; PATHURI, Srinivasarao; GOLIVI, Ramamohana Rao; JAYACHANDRA, Sureshbabu; (36 pag.)WO2020/75199; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 59713-58-5, 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. 59713-58-5, name is Ethyl 4-chlorothieno[2,3-b]pyridine-5-carboxylate, molecular formula is C10H8ClNO2S, 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.

REFERENCE EXAMPLE 11 4-Chlorothieno[2,3-b]pyridine-5-carboxylic acid A mixture of ethyl 4-chlorothieno[2,3-b]pyridine-5-carboxylate (800 mg, 3.31 mmol) [Khan, M. A.; Guarconi, A. E., J. Heterocyclic Chem., 14, 807 (1977)] in 15 mL of ethanol and 5 mL of 2.5 N sodium hydroxide is heated at reflux for 90 minutes. The mixture is cooled to 0C and the pH is adjusted to 4 by the addition of 2 N hydrochloric acid. The mixture is stirred at room temperature and the resulting precipitate is collected by filtration and washed with water to provide 250 mg of 4-chlorothieno[2,3-b]pyridine-5-carboxylic acid as a white solid, mp 172-174 C.; 1H NMR (DMSO-d6) delta7.62 (d, J=6 Hz, 1H), 8.14 (d, J=6 Hz, 1H), 8.94 (s, 1H); MS 212.0 (M-H)-. Analysis for C8H4ClNO2S: Calcd: C, 44.98; H, 1.89; N, 6.56 Found: C, 44.99; H, 2.14; N, 6.43.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 59713-58-5, Ethyl 4-chlorothieno[2,3-b]pyridine-5-carboxylate.

Reference:
Patent; Wyeth; US2004/242883; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 891855-87-1, 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.891855-87-1, name is 4-Amino-2-ethylaminopyridine, molecular formula is C7H11N3, molecular weight is 137.18, as common compound, the synthetic route is as follows.

0.94 g of the compound described under INT12) is dissolved in 50 ml 1-propanol. 1.85 g of the compound described under INTT5) is added and it is stirred for 4 hours under reflux. After cooling, the reaction mixture is filtered. After purification by chromatography on silica gel, the solid substance yields 1.48 g of title compound as pH-dependent 5-(E/Z)-isomer mixture. 1 H-nMR (DMSO-d6, stored over K2CO3, main isomer): delta=1.13 (t, 3H); 1.26 (t, 3H); 3.24 (pentuplet, 2H); 4.25 (q, 2H); 4.72 (d, 1H); 5.28 (d, 1H); 5.39 (d, 1H); 5.90-6.07 (m, 1H); 6.25 (d, 1H); 6.44 (dd, 1H); 6.49 (t, 1H); 7.85 (d, 1H); 8.13 (s, 1H); 10.47 (s, 1H) ppm.

Statistics shows that 891855-87-1 is playing an increasingly important role. we look forward to future research findings about 4-Amino-2-ethylaminopyridine.

Reference:
Patent; Schulze, Volker Klaus; Eis, Knut; Wortmann, Lars; Kosemund, Dirk; Prien, Olaf; Siemeister, Gerhard; Hess-Stumpp, Holger; Eberspaecher, Uwe; Brittain, Dominic E.A.; Islam, Imadul; US2007/15759; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 142896-15-9, Methyl 2,6-dimethylisonicotinate, 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, Computed Properties of C9H11NO2, blongs to pyridine-derivatives compound. Computed Properties of C9H11NO2

General procedure: Compound 100: 3-(2,6-Dimethyl-pyridin-4-yl)-3-oxo-propionitrile. Compound 100 was obtained according to general procedure VII(ii) starting from compound 99. Compound 100 was used in the next step without further purification. M/Z (M+H)+ = 175.2. Method (ii): Under anhydrous condition, to a solution of acetonitrile (2.0 equiv.) in THF (c=0.4 mol.L-1) cooled at -78C, BuLi (1.6N in hexane – 2 equiv.) was added dropwise. The reaction mixture turned light beige. The mixture was stirred for 1 hour at -78C, then the acid derivative (acid chloride or ester – 1.0 equiv.) was added dropwise. The reaction mixture was stirred at -78C for 1 hour, after which time it was allowed to warm to 0C and hydrolysed with AcOH. The reaction mixture was concentrated, dried under reduced pressure at 50C with P2O5 for 18 hours.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,142896-15-9, Methyl 2,6-dimethylisonicotinate, and friends who are interested can also refer to it.

Reference:
Patent; Domain Therapeutics; Mayer, Stanislas; Schann, Stephan; EP2666775; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 67938-76-5, name is (5-Chloropyridin-2-yl)methanamine, molecular formula is C6H7ClN2, 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. name: (5-Chloropyridin-2-yl)methanamine

To a mixture of A-l (2.00 g, 14.03 mmol) in THF (30 mL) was added TFAA (4.42 g, 21.05 mmol), then the mixture was stirred at 20 °C for 16 hours. The mixture was concentrated and the resulting residue was diluted with 0 (50 mL), and extracted with EtOAc (100 mL x 2). The combined organic phase was washed with sat. Na2C03 (30 mL), water (50 mL) and brine (50 mL), dried over Na2S04, filtered and concentrated to give A-2 (3.10 g, 12.99 mmol) as a solid. 1H NMR (400MHz, CDC13) = 8.54 (d, 1H), 7.85 – 7.60 (m, 2H), 7.25 (d, 1H), 4.63 (d, 2H).

With the rapid development of chemical substances, we look forward to future research findings about 67938-76-5.

Reference:
Patent; PRAXIS PRECISION MEDICINES, INC.; REDDY, Kiran; MARTINEZ BOTELLA, Gabriel; GRIFFIN, Andrew, Mark; MARRON, Brian, Edward; (141 pag.)WO2018/98491; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 880870-13-3, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 880870-13-3, name is 5-Bromo-2-chloro-4-methoxypyridine. This compound has unique chemical properties. The synthetic route is as follows.

A solution of 5-bromo-2-chloro-4-methoxypyridine (5.0 g, 22.48 mmol) in DMF (80 mL) was purged with nitrogen for 15 min. Al this point, Zn(CN)2 (3.96 g, 33.7 mmol) and Pd(Ph3P)4 (2.60 g, 2.25 mmol) were added, successively. The resulting suspension was stirred at 95 0C for 12 h under nitrogen atm. The reaction mixture was cooled to ambient temperature, filtered to remove inorganic solid. The solvent (DMF) was evaporated to provide the crude residue as an oil, which was purified on silica gel and eluted with 0-30% ethyl acetate / hexanes to afford the product. 1H NMR (500 MHz, DMSO-^), delta 8.69 (s, IH), 7.50 (s, IH), 4.04 (s, 3H); LC/MS (M+l)+ – 168.96; tR – 2.05 min

According to the analysis of related databases, 880870-13-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP &; DOHME CORP.; PASTERNAK, Alexander; SHAHRIPOUR, Aurash; TANG, Haifeng; TEUMELSAN, Nardos, H.; YANG, Lihu; ZHU, Yuping; WALSH, Shawn, P.; WO2010/129379; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem