Category: pyridine-derivatives

Application of 71255-09-9 ,Some common heterocyclic compound, 71255-09-9, molecular formula is C7H7NO2, 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: Et3N (1.0 equiv) was added to a suspension of 2-(4-bromo-2,5-dimethoxyphenyl)ethanamine hydrochloride (2C-B*HCl, 1.0 mmol) and the required aldehyde (1.1 equiv) in EtOH (10 mL) and the reaction was stirred until formation of the imine was complete according to TLC or GC (between 30 min and 3 h depending on the aldehyde). NaBH4 (2.0 mmol) was then added and the reactionwas stirred for another 30 min. The reaction mixture was concentratedunder reduced pressure and the residue was partitioned between CH2Cl2 and water (30 mL, 1:1). The organic layer was isolated and the aqueous layer was extracted with CH2Cl2 (2 x 15 mL). The combined organic extracts were dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography (CH2Cl2/MeOH/NH3 98:2:0.04). The purified free base was dissolved in EtOH (2 mL) and HCl (1 M in EtOH, 2 mL) was added and the resulting solution was diluted with Et2O until a precipitate was formed. The crystals were collected by filtration and dried under reduced pressure to provide the desired products.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,71255-09-9, its application will become more common.

Reference:
Article; Hansen, Martin; Jacobsen, Stine Engesgaard; Plunkett, Shane; Liebscher, Gudrun Eckhard; McCorvy, John D.; Braeuner-Osborne, Hans; Kristensen, Jesper Langgaard; Bioorganic and Medicinal Chemistry; vol. 23; 14; (2015); p. 3933 – 3937;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 15855-06-8, name is 2-Chloro-6-methoxypyridine-4-carboxylic Acid, the common compound, a new synthetic route is introduced below. HPLC of Formula: C7H6ClNO3

b) To a suspension of 2-chloro-6-methoxy-isonicotinic acid (244 g, 1.30 mol) in methanol (2.5 L), H2SO4 (20 mL) is added. The mixture is stirred at reflux for 24 h before it is cooled to 0 C. The solid material is collected, washed with methanol (200 mL) and water (500 mL) and dried under HV to give 2-chloro-6-methoxy-isonicotinic acid methyl ester (165 g) as a white solid; LC-MS: tR=0.94 min, [M+1]+=201.89.

The synthetic route of 15855-06-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bolli, Martin; Lescop, Cyrille; Mathys, Boris; Morrison, Keith; Mueller, Claus; Nayler, Oliver; Steiner, Beat; US2012/108638; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 851386-35-1, 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 851386-35-1, name is 2,3-Difluoro-5-iodopyridine. This compound has unique chemical properties. The synthetic route is as follows.

Step 1: 1-(3-Fluoro-5-iodo-pyridin-2-ylamino)-2-methyl-propan-2-ol 2,3-Difluoro-5-iodopyridine (500 mg, 2.07 mmol) was dissolved in NMP (500 muL) and pyridine (201 mul, 2.49 mmol, 1.2 equiv.) and 1-amino-2-methylpropan-2-ol (555 mg, 6.22 mmol, 3 equiv.) were added at room temperature. The mixture was stirred for 16 hours at 100° C. The reaction mixture was cooled and extracted with saturated NaHCO3 solution and two times with a small volume of dichloromethane. The crude product was purified by flash chromatography by directly loading the dichloromethane layers onto a silica gel column and eluting with an ethyl acetate:heptane gradient 0:100 to 100:0. The desired 1-(3-fluoro-5-iodopyridin-2-ylamino)-2-methylpropan-2-ol (590 mg, 1.9 mmol, 91.7percent yield) was obtained as a colorless oil, MS: m/e=311.0 (M+H+).

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 851386-35-1, 2,3-Difluoro-5-iodopyridine.

Reference:
Patent; Green, Luke; Guba, Wolfgang; Jaeschke, Georg; Jolidon, Synese; Lindemann, Lothar; Ricci, Antonio; Rueher, Daniel; Stadler, Heinz; Vieira, Eric; US2011/251169; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 65-22-5, name is 3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde hydrochloride. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C8H10ClNO3

General procedure: In a round bottom flask, pyridoxal hydrochloride (0.201g; 1.0mmol) was added to methanol (15mL) and the resulting suspension was subjected to magnetic stirring at room temperature until complete dissolution of the pyridoxal molecule. Then, the corresponding aniline (0.120g of 2-fluoroaniline; 0.130g of 2-chloroaniline, 0.170g of 2-bromoaniline or 0.220g of 2-iodoaniline; 1.0mmol for each) dissolved in methanol (5 mL) was added. The resulting mixture was kept under magnetic stirring at reflux temperature for 2.0h. After this period, the flask contents were cooled to room temperature and the solvent evaporated. The resulting solid was washed with small portions of ice water and diethyl ether and dried in a desiccator with CaCl2. For the synthesis of the ligand containing aniline, the same conditions were used, but without potassium hydroxide (0.093g of aniline was added to 15mL of methanol and 1mmol of pyridoxal hydrochloride; 0.201g). Properties – orange crystals, yield 85%. Melting point: 207C. Anal.Calc. for [C14H13BrN2O2] C, 47.02; H, 3.95; N, 7.83. Found: C, 46.93; H, 3.90; N, 7.79%. IR (KBr pellets, cm-1): 3209 [w, nu(O-H)]; 1627 [m, nu(C=N)]; 1387 [m, nu(C-N)], 1257 [s, nu(C-O)phenol], 1033 [s, nu(C-O)alcohols], 694 [m, nu(C-Br)alcohols] and 620 [s, nu(O-H)alcohols] (w=weak; m=medium; s=strong). 1H NMR (ppm, DMSO-d6): delta 2.46 (s, 3H, CH3); 4.80 (s, 2H, CH2); 7.32-7.81 (m, 4H, Ar); 8.03 (s, 1H, Py) and 9.21 (s, 1H, CHimine)

With the rapid development of chemical substances, we look forward to future research findings about 65-22-5.

Reference:
Article; Pereira, Mateus Brum; Fontana, Liniquer Andre; Siqueira, Josieli Demetrio; Auras, Bruna L.; da Silva, Marcos P.; Neves, Ademir; Gabriel, Philipe; Terenzi, Hernan; Iglesias, Bernardo Almeida; Back, Davi Fernando; Inorganica Chimica Acta; vol. 469; (2018); p. 561 – 575;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1604-14-4, 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. 1604-14-4, name is 2,6-Dichloro-isonicotinic acid ethyl ester, molecular formula is C8H7Cl2NO2, 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.

Step A: 2,6-Dichloro-isonicotinic acid ethyl ester (45 mmol), Cs2CO3 (1.1 eq.) and Phenol (1 eq.) is dissolved in DMF (100 ml). The reaction suspension is heated to 150 0C for 10 minutes in the microwave. After filtration, the solvent is removed in vacuo. 2-Chloro-6-phenoxy-isonicotinic acid ethyl ester is obtained after column chromatography (Heptan / ethyl acetate) as a colorless oil in a yield of 57 %. HPLC (Method A): 3.59 min, LCMS (Method A): 2.81 min, 287.2 m/z (MH+).

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 1604-14-4, 2,6-Dichloro-isonicotinic acid ethyl ester.

Reference:
Patent; MERCK PATENT GmbH; WO2009/106209; (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. 5345-47-1, name is 2-Aminonicotinic acid, molecular formula is C6H6N2O2, 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. Product Details of 5345-47-1

General procedure: Method B: To a solution of 3-aminopyridine-2-carboxylic acid (2.74 g, 20 mmol) in anhydrous DMF (100 mL) was added EDC (4.2 g, 22 mmol), HOBt (2.97 g, 22 mmol) and triethylamine (8.2 mL, 60 mmol). alpha-Amino acid methyl ester (22 mmol) was added, and the reaction mixture was stirred overnight. Water (100 mL) was added, and the mixture was extracted with methylene chloride (4 × 100 mL), dried over MgSO4 and concentrated. The compound was purified by silica gel chromatography to give the oil-like open product 6; this was then dissolved in THF (125 mL) under argon. Sodium hydride (0.93 g, 60% dispersion in oil, 26.8 mmol) was added, and the reaction mixture was stirred overnight. Water (5 mL) was carefully added, and the resulting white precipitate was collected. The precipitate was dissolved in ethyl acetate (200 mL), washed with water (50 mL) and brine (50 mL), dried over MgSO4 and concentrated to give product 8.

With the rapid development of chemical substances, we look forward to future research findings about 5345-47-1.

Reference:
Article; El Bouakher, Abderrahman; Laborie, Helne; Aadil, Mina; El Hakmaoui, Ahmed; Lazar, Said; Akssira, Mohamed; Viaud-Massuard, Marie-Claude; Tetrahedron Letters; vol. 52; 39; (2011); p. 5077 – 5080;,
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. 1210419-26-3, name is Methyl 6-bromo-5-fluoropicolinate. This compound has unique chemical properties. The synthetic route is as follows. Safety of Methyl 6-bromo-5-fluoropicolinate

In a sealed tube to a mixture of methyl 6-bromo-5-fluoropyridine-2-carboxylate (374 mg, 1.60 mmol) and (2,6-difluoro-3-methoxyphenyl)boronic acid (150 mg, 0.798 mmol) in THF (6.0 mL) and water (0.6 mL) was added potassium fluoride (153 mg, 2.64 mmol). The reaction mixture was purged with N2 for 5 min., then tris(dibenzylideneacetone)dipalladium (0) (180 mg, 0.20 mmol) and tri-tert-butylphosphine (81 mg, 0.40 mmol) were added subsequently. The reaction mixture was then heated at 100 C. for 30 min. After filtration and concentration of the solution under reduced pressure, the residue was purified by silica gel column chromatography using CombiFlash (0 to 40% EtOAc in hexanes) to give the sub-title compound as a white powder (83.3 mg, 35%). LCMS calc. for C14H11F3NO3 (M+H)+: m/z=298.1. Found: 298.2.

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, 1210419-26-3, Methyl 6-bromo-5-fluoropicolinate.

Reference:
Patent; INCYTE CORPORATION; Xue, Chu-Biao; Li, Yun-Long; Geng, Hao; Pan, Jun; Wang, Anlai; Zhang, Ke; Yao, Wenqing; Zhang, Fenglei; Zhuo, Jincong; US2014/200227; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 15513-52-7, 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 15513-52-7, name is 2,6-Dimethyl-3-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of 2,6-dimethyl-3-nitropyridine (200mg, 1.3 mmol, 1.0 eq) in ethanol (10 mL) was added 40 % aqs. formaldehyde (15 mL) followed by water (10 mL) room temperature and stirred for 48 h at 200 C. The aqs solvent was evaporated and crude purified by silica gel column chromatography (100-200 mesh) using ethyl acetate/petrol ether (2 : 8) as eluent to get 2-(6-methyl-5-nitropyridin-2-yl)ethanol (220 mg, 55 %) as yellow liquid.

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 15513-52-7, 2,6-Dimethyl-3-nitropyridine.

Reference:
Patent; GRUeNENTHAL GMBH; FRANK, Robert; BAHRENBERG, Gregor; CHRISTOPH, Thomas; LESCH, Bernhard; WO2013/13815; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1072-97-5, 5-Bromopyridin-2-amine, 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, Safety of 5-Bromopyridin-2-amine, blongs to pyridine-derivatives compound. Safety of 5-Bromopyridin-2-amine

5-bromo-2-aminopyridine (5.19 g, 30 mmol) was dissolved in 100 mL of anhydrous dichloromethane. 20 ml of triethylamine was added. In ice bath conditions, Slowly add acetyl chloride (2.54 ml) to the above solution. After the addition is complete, Remove the ice bath, The reaction was allowed to rise to room temperature overnight (i.e., reaction for 12 h). After the reaction, Dilute with dichloromethane, Washed (30ml × 3), Wash with saturated NaHCO 3 solution (30ml × 3), Saturated NaCl wash (30ml), The organic phase was dried over anhydrous Na 2 SO 4 . Column chromatography gave 5.65 g of a white solid, yield 88%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1072-97-5, 5-Bromopyridin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; Xi’an Jiaotong University; Zhang Jie; Pan Xiaoyan; Liang Liyuan; Lu Wen; Wang Sicen; He Langchong; Si Ru; Wang Jin; (15 pag.)CN109734660; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 5975-12-2, 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.5975-12-2, name is 2,4-Dichloro-3-nitropyridine, molecular formula is C5H2Cl2N2O2, molecular weight is 192.9876, as common compound, the synthetic route is as follows.

Step 3a’. 2-Chloro-N-(4-methoxybenzyl)-3-nitropyridin-4-amine (Compound 0201) To a solution of compound 0109 (1 g, 5.18 mmol) in was in DMF (8.6 mL) was added (4-methoxyphenyl)methanamine (0.71 g, 5.18 mmol) and triethylamine (0.644 mL). The solution was stirred at room temperature for 2 h. The mixture was evaporated to to remove DMF. The resulting mixture was purified by column chromatography on silica gel (EtOAc/petroleum at 10:1) to obtain the title compound 0201 as a yellow solid (1.32 g, 87%): LCMS: 294 [M+1]+; 1H NMR (DMSO-d6) delta 3.72 (s, 3H), 4.40 (d, 2H, J=6.3 Hz), 6.81 (d, 1H, J=5.7 Hz), 6.91 (d, 2H, J=9.0 Hz), 7.25 (d, 2H, J=8.4 Hz), 7.95 (d, 1H, J=5.4 Hz), 8.02 (t, 1H, J=5.7 Hz).

The chemical industry reduces the impact on the environment during synthesis 5975-12-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Cai, Xiong; Qian, Changgeng; Zhai, Haixiao; US2008/234314; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem