Category: 13534-99-1

Electric Literature of 13534-99-1, 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. 13534-99-1, name is 2-Amino-3-bromopyridine, molecular formula is C5H5BrN2, 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.

General procedure: To a solution of 2a, 2c or 2h (3 mmol, 0.5 g) in ethylene glycol (5 mL) was added successively the boronic acid (4.5 or 9.0 mmol, 1.5 or 3 equiv), Pd(PPh3)4 (1molpercent), and a solution of K3PO4 (6 mmol, 2 equiv) inwater (2 mL). The reaction mixture was heated at 80°C for 16 h and was then hydrolyzed with a 1 M solution of sodium hydroxide (20 mL). The aqueous phase was extracted with ethylacetate (3 x 30 mL) and the combined organic layers were washed with brine (50 mL), dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel with petroleum ether/EtOAc (60/40) as eluent.

According to the analysis of related databases, 13534-99-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Silpa, Laurence; Niepceron, Alisson; Laurent, Fabrice; Brossier, Fabien; Penichon, Melanie; Enguehard-Gueiffier, Cecile; Abarbri, Mohamed; Silvestre, Anne; Petrignet, Julien; Bioorganic and Medicinal Chemistry Letters; vol. 26; 1; (2016); p. 114 – 120;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 13534-99-1 ,Some common heterocyclic compound, 13534-99-1, molecular formula is C5H5BrN2, 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.

3-Bromopyridin-2-amine (30 g, 168 mmol) and ethoxycarbonyl isothiocyanate (24.8 g, 21.3 mL, 185 mmol) were dissolved in dioxane (300 mL) and stirred at room temperature. After 4 hours further ethoxycarbonyl isothiocyanate (1 mL, 8.4 mmol) was added. After 1 hour the solvent was evaporated and the residue dried in high vacuum for 12 hours. The title compound was obtained as a light yellow solid (51.2 g, 100%) and was used crude for the next step.MS ISP (m/e): 304.0/ 305.9 (100/ 73) [(M+H)+].1H NMR (CDC13, 300 MHz): delta (ppm) = 8.41 (m, 1H) 7.99-7.96 (m, 1H), 7.11-7.07 (m, 1H), 4.32 (q, 2H), 1.36 (t, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13534-99-1, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BAUMANN, Karlheinz; FLOHR, Alexander; GOETSCHI, Erwin; GREEN, Luke; JOLIDON, Synese; KNUST, Henner; LIMBERG, Anja; LUEBBERS, Thomas; THOMAS, Andrew; WO2011/101304; (2011); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 13534-99-1, name is 2-Amino-3-bromopyridine. This compound has unique chemical properties. The synthetic route is as follows. Formula: C5H5BrN2

Ethyl isocyanatoformate (52.5?g, 397?mmol) is added dropwise at 5?C to a solution of 2-amino-3-bromopyridine (33a) (66?g, 378?mmol) in DCM (660?mL). After stirring for 16?h at RT the reaction mixture is concentrated under reduced pressure to give crude product, which is washed with PE and dried. Yield: 105?g (87%). LCMS (ESI+) calculated for C9H10BrN3O2S [M+H]+ m/z 303.9755, found 304.0. 1H NMR (400?MHz, (CD3)2SO) delta 11.43 (br s, 2H), 8.49 (dd, J?=?4.6, 1.5?Hz, 1H), 8.17 (dd, J?=?7.9, 1.5?Hz, 1H), 7.33 (dd, J?=?7.9, 4.7?Hz, 1H), 4.23 (q, J?=?7.1?Hz, 2H), 1.27 (t, J?=?7.1?Hz, 3H). TLC (silica gel, PE/EE 3:1): Rf?=?0.4.fx8

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, 13534-99-1, 2-Amino-3-bromopyridine.

Reference:
Article; Gerlach, Kai; Hobson, Scott; Eickmeier, Christian; Gross, Ulrike; Braun, Clemens; Sieger, Peter; Garneau, Michel; Hoerer, Stefan; Heine, Niklas; Bioorganic and Medicinal Chemistry; vol. 26; 12; (2018); p. 3227 – 3241;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 13534-99-1, 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. 13534-99-1, name is 2-Amino-3-bromopyridine. A new synthetic method of this compound is introduced below.

The compound 14-1 (200 mg) was dissolved in a mixed solvent of tetrahydrofuran (1.2 ml) and triethylamine (7 ml). Ethynyl (trimethyl) silane (227 mg) , copper (I) iodide (8.8 mg) and dichloropalladium- triphenyl phosphine (32.5 mg) were added and the mixture was sealed in a tube. After stirring the mixture at 900C for 22 hours, the reaction mixture was added to water to terminate the reaction. The aqueous layer was extracted with ethyl acetate, and the organic layer was washed with brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The resulting crude product was purified by silica gel column chromatography to obtain the title compound (244 mg) . IH NMR (400 MHz, CDCl3) (ppm) : 0.26 (s, 9H), 5.08 (br. s., 2H), 6.62 (br. s., IH), 7.54d, J=7.2 Hz, IH), 8.05 (br. s. , IH) .

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13534-99-1, 2-Amino-3-bromopyridine, and friends who are interested can also refer to it.

Reference:
Patent; Eisai R&D Management CO., LTD.; MOTOKI, Takafumi; KANEKO, Toshihiko; YAMAMOTO, Noboru; KHAN, Afzal; WO2010/13794; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

13534-99-1, Adding a certain compound to certain chemical reactions, such as: 13534-99-1, 2-Amino-3-bromopyridine, 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, 13534-99-1, blongs to pyridine-derivatives compound.

Example 28: 8,9-Dimethoxy-5H-benzo[cU1 ,81naphthyridin-6-one (28); 2-Amino-3-bromopyridine (500 mg, 2.89 mmol), 4,5-dimethoxy-2- methoxycarbonylphenylboronic acid (1.04 g, 4.33 mmol), palladium(ll) acetate (30 mg, 0.12 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (90 mg, 0.23 mmol), and potassium carbonate (1.2 g, 8.67 mmol) were dissolved in dioxane / H2O (1 1 ml_, 10 / 1 , v / v), and stirred overnight at 100 0C. The reaction mixture was concentrated, suspended in EtOAc / H2O, and filtered. The precipitate was washed with EtOAc / H2O, and dried under vacuum to provide 27 (600 mg, 81 % yield) as a white solid. LC-MS (M+H = 257, obsd. = 257). 1H NMR (400 MHz, d6- DMSO) : delta 8.83 (dd, 1 H), 8.42 (dd, 1 H), 7.92 (s, 1 H), 7.71 (s, 1 H), 7.29 (m, 1 H), 4.04 (s, 3H), 3.91 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13534-99-1, its application will become more common.

Reference:
Patent; MERCK SERONO S.A.; WO2009/108670; (2009); 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. 13534-99-1, name is 2-Amino-3-bromopyridine, molecular formula is C5H5BrN2, 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. 13534-99-1

Step A: 3-Phenylpyridin-2-amineTo a deoxygenated solution of 3-bromopyridin-2-amine (5.00 g, 28.9 mmol), phenylboronic acid (4.23 g, 34.7 mmol) and sodium carbonate (9.2 g, 87 mmol) in 1,4-dioxane (60 mL) and water (30 mL) was added PdCl2(PPh3)2 (1.01 g, 1.44 mmol). The resulting mixture was heated at reflux for 4 h, then cooled, filtered, and concentrated. The residue was partitioned between brine (50 mL) and ethyl acetate (30 mL x 3). The combined organic layers were washed with brine, dried over Na2S04, and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate in petroleum ether: 20-50%) to give the title compound. XH NMR (400 MHz, CDC13) delta 8.09 (d, J= 3.5 Hz, 1H), 7.51-7.43 (m, 4H), 7.41-7.35 (m, 2H), 6.76 (dd, J= 7.0, 5.1 Hz, 1H), 4.61 (br s, 2H).

The chemical industry reduces the impact on the environment during synthesis 13534-99-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MSD R&D (CHINA) CO., LTD.; MITCHELL, Helen; FRALEY, Mark, E.; COOKE, Andrew, J.; CHEN, Yi-Heng; STUMP, Craig, A.; ZHANG, Xu-Fang; MCCOMAS, Casey, C.; SCHIRRIPA, Kathy; MCWHERTER, Melody; MERCER, Swati, P.; BABAOGLU, Kerim; MENG, Dongfang; WU, Jane; LIU, Ping; WOOD, Harold, B.; BAO, Jianming; LI, Chun Sing; MAO, Qinghua; QI, Zhiqi; (263 pag.)WO2015/148344; (2015); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

13534-99-1 ,Some common heterocyclic compound, 13534-99-1, molecular formula is C5H5BrN2, 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.

2-Amino-3-bromopyridine (VII-41) (5.00 g, 28.9 mmol) was dissolved in ethanol (100 mL), sodium hydrogencarbonate (3.64 g, 43.3 mmol) and 2-chloroacetaldehyde (7.1 mL, 43 mmol) were added, and the mixture was stirredunder refluxing with heating for 4 hr. The mixture was allowed to cool, and the solvent was evaporated under reducedpressure. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed withsaturated brine, dried over anhydrous sodium sulfate, and filtered. The solvent was evaporated under reduced pressure.The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate = 70:30 ? 40:60) to give 8-bromoimidazo[1,2-a]pyridine (VII-42) (yield 5.71 g, quantitative

According to the analysis of related databases, 13534-99-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kaken Pharmaceutical Co., Ltd.; WATANABE, Atsushi; SATO, Yuuki; OGURA, Keiji; TATSUMI, Yoshiyuki; (331 pag.)EP3351533; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

13534-99-1, A common compound: 13534-99-1, name is 2-Amino-3-bromopyridine,molecular formula is C5H5BrN2, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Preparative Example 13 Step 1: 3-cyclopropylpyridin-2-amine To a solution of 3-bromopyridin-2-amine (10.0 g, 58.13 mmol) in toluene (100 mL) and water (10 mL) were added cyclopropylboronic acid (6.49 g, 75.57 mmol), tricyclohexylphosphine (1.63 g, 5.81 mmol), tri-potassium phosphate trihydrate (54 g, 0.2 mol) and palladium(II) acetate (652 mg, 2.91 mmol). The reaction mixture was purged with nitrogen for 2 min and heated to 90 ¡ãC for 16 h and subsequently concentrated to dryness in vacuo. The resulting viscous mass was diluted with water and extracted with ethyl acetate (3 x 150 mL). The combined organic layers were dried over sodium sulfate and concentrated to dryness in vacuo. The resulting residue was purified by column chromatography (silica gel, 100-200 mesh, 10percent to 30percent ethyl acetate in hexane) affording 3- cyclopropylpyridin-2-amine (7.0 g, 90percent): lU NMR (400 MHz, Chloroform-d) delta 7.93 – 7.91 (m, 1H), 7.24 – 7.21 (m, 1H), 6.59 – 6.56 (m, 1H), 4.76 (s, 2H), 1.63 – 1.57 (m, 1H), 0.92 – 0.87 (m, 2H), 0.59 – 0.57 (m, 2H).

With the rapid development of chemical substances, we look forward to future research findings about 13534-99-1.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; ESTRADA, Anthony; HUESTIS, Malcolm; KELLAR, Terry; PATEL, Snahel; SHORE, Daniel; SIU, Michael; (260 pag.)WO2016/142310; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.13534-99-1, name is 2-Amino-3-bromopyridine, molecular formula is C5H5BrN2, molecular weight is 173.01, as common compound, the synthetic route is as follows.13534-99-1

Step 3. tert-butyl 4-(2-aminopyridin-3-yl)-2-fluorobenzoate A slurry of tert-butyl 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (5.1 g, 15.83 mmol), 3-bromoaminopyridine (3.01 g, 17.41 mmol) and Pd(PPh3)4 (0.732 g, 0.633 mmol) in n-butanol (50 mL) and 2.0 M Na2CO3aqueous solution (19.79 mL, 39.6 mmol) was degassed, and then heated to 100¡ã C. overnight. The reaction was cooled, and diluted with ethyl acetate. The layers were separated, and the organics were washed with brine, filtered over celite and concentrated. The crude was purified by flash chromatography eluting with 10-50percent ethyl acetate/heptane to provide 3.41 g of tert-butyl 4-(2-aminopyridin-3-yl)-2-fluorobenzoate in 75percent yield.

Statistics shows that 13534-99-1 is playing an increasingly important role. we look forward to future research findings about 2-Amino-3-bromopyridine.

Reference:
Patent; Novartis AG; Bagdanoff, Jeffrey T.; Ding, Yu; Han, Wooseok; Huang, Zilin; Jiang, Qun; Jin, Jeff Xianming; Kou, Xiang; Lee, Patrick; Lindvall, Mika; Min, Zhongcheng; Pan, Yue; Pecchi, Sabina; Pfister, Keith Bruce; Poon, Daniel; Rauniyar, Vivek; Wang, Xiaojing Michael; Zhang, Qiong; Zhou, Jianguang; Zhu, Shejin; (366 pag.)US9242996; (2016); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.13534-99-1, name is 2-Amino-3-bromopyridine, molecular formula is C5H5BrN2, molecular weight is 173.01, as common compound, the synthetic route is as follows.13534-99-1

equipped with a mechanical stirring three 500mL flask, 30g2- amino-3-bromo-pyridine, 52.8 g as an associated boronic acid pinacol ester, 300mL1,4- dioxane, 4.2gPd (dppf)2Cl2, 59.3g of anhydrous potassium acetate, purged with nitrogen three times, heated to about 80 open overnight.TLC the reaction was complete, cooling, filtration, the filter cake washed twice with 30mL dichloromethane and the filtrate was concentrated to dryness, 200mL of methanol and 20g active carbon was stirred at room temperature overnight, filtration.Concentrated to dryness to give an oil, and petroleum ether was added 15mL 200mL MTBE heating overnight, filtered to give 28g2-amino-4-boronic acid pinacol ester in a yield of 72.8%.

Statistics shows that 13534-99-1 is playing an increasingly important role. we look forward to future research findings about 2-Amino-3-bromopyridine.

Reference:
Patent; Shanghai Rainbow Chemistry Co.,Ltd; Wu, Gang; Yan, taotao; Wei, xianli; (13 pag.)CN102786543; (2016); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem