Category: pyridine-derivatives

Application of 1072-98-6 , The common heterocyclic compound, 1072-98-6, name is 2-Amino-5-chloropyridine, molecular formula is C5H5ClN2, 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.

Step 1. Ethyl 6-Chloroimidazo[1,2-a]pyridine-2-carboxylate To 2-amino-5-chloropyridine (Aldrich; 2.19 g) in dimethoxyethane (Aldrich; 25 mL) is added ethyl 2-bromopyruvate (Aldrich; 2.37 mL). After stirring overnight, the solid is collected and washed with diethyl ether. The solid is dried under reduced pressure at 45 C. and then is partitioned between dichloromethane and aqueous sodium bicarbonate. The organic phases are dried over sodium sulfate and concentrated to give 3.05 g of ethyl 6-chloroimidazo[1,2-a]pyridine-2-carboxylate. 1 H NMR (CDCl3) delta1.44, 4.46, 7.23, 7.64, 8.16, 8.21.

The synthetic route of 1072-98-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pharmacia & Upjohn Company; US5912246; (1999); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 59290-81-2, 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. 59290-81-2, name is 2-Methyl-5-nitro-3-pyridinecarboxylic acid, molecular formula is C7H6N2O4, 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.

REFERENTIAL EXAMPLE 12 synthesis of N,N-diethyl 2-bromomethyl-5-nitronicotinamide To a solution of 0.6 g of 2-methyl-5-nitronicotinic acid and 3 ml of diethylamine in 100 ml of chloroform was added 20 g of phosphorus pentachloride and the resulting mixture was stirred at 60 C. for 3 hours. After cooling, the chloroform layer was separated, the solvent was distilled off under reduced pressure, the residue was mixed with water, neutralized with sodium bicarbonate and extracted with ethyl acetate. The extract was dried, concentrated and chromatographed over silica gel to give 0.4 g of the desired product as oil. Analysis for C11 H15 N3 O3: Calcd. (%): C, 55.68; H, 6.37; N, 17.71. Found (%): C, 55.57; H, 6.43; N, 17.56. To a solution of 0.4 g of N,N-diethyl-2-methyl-5-nitronicotinamide in 1.5 ml of acetic acid was added a solution of 0.27 g of bromine in 1.0 ml of acetic acid and the resulting mixture was stirred at 120 C. for 1.5 hours. The reaction mixture was poured into ice-water, made alkaline with sodium bicarbonate and extracted with ethyl acetate. The extract was washed with water, dried and the solvent was distilled off to give brown oily substance. This substance was chromatographed over silica gel to give 0.1 g of unreacted starting material and 0.28 g of N,N-diethyl 2-bromomethyl-5-nitronicotinamide. mp 62 – 64 C.

According to the analysis of related databases, 59290-81-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sankyo Company Limited; US4053608; (1977); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 59942-87-9, 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. 59942-87-9, name is Pyrazolo[1,5-a]pyridin-2(1H)-one, molecular formula is C7H6N2O, 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.

A solution of pyrazolo[1,5-a]pyridin-2-ol (776 mg, 5.78 mmol), K2CO3 (2.4 g, 17.3 mmol), 1-bromo-4-chlorobutane (1.35 mL, 11.6 mmol) and sodium iodide (catalytic amount) in 20 mL of DMF was stirred for 18 h at room temperature. The resulting mixture was filtered, the solid washed with DMF and the organic filtrate concentrated. The residue was poured into diethyl ether and the generated precipitate filtered and discarded. The organic filtrate was washed with water and the organic layer dried (Na2SO4) and concentrated under vacuum to afford 1.35 g (quantitative) of brown oil.

According to the analysis of related databases, 59942-87-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Laboratorios del. Dr. Esteve, S.A.; Diaz-Fernandez,Jose-Luis; Cuberes-Altisent,Mª Rosa; EP2631236; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 21427-61-2, 5-Chloro-2-hydroxy-3-nitropyridine, 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, 21427-61-2, blongs to pyridine-derivatives compound. Quality Control of 5-Chloro-2-hydroxy-3-nitropyridine

a) 3-amino-5-chloropyridin-2-ol A mixture of 5-chloro-3-nitropyridin-2-ol (30.0 g), iron (14.5 g), ammonium chloride (46.5 g) and ethanol/water (300 mL, 3/1, v/v) was stirred at 90 C. for 2 hr. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (20.0 g). MS: [M+H]+ 145.3.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,21427-61-2, its application will become more common.

Reference:
Patent; Takeda Pharmaceutical Company Limited; FUJIMOTO, Jun; LIU, Xin; KURASAWA, Osamu; TAKAGI, Terufumi; CARY, Douglas Robert; BANNO, Hiroshi; ASANO, Yasutomi; KOJIMA, Takuto; (159 pag.)US2019/169166; (2019); A1;,
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. 57963-08-3, name is 5,6-Dimethylpyridin-2-amine, the common compound, a new synthetic route is introduced below. Safety of 5,6-Dimethylpyridin-2-amine

Example 130 Synthesis of 5,6-dimethylpyridin-2-amine. To a solution of 5,6-dimethylpyridin-2-amine (1.0 g, 8.2 mmol) in DMF (10 mL) was added 1,3-dichloropropan-2-one (4.2 g, 32.8 mmol). The resulting mixture was stirred at 90 C. for 2 h. The reaction mixture was diluted with H2O (150 mL) and extracted with ethyl acetate (3*30 mL). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated. The residue was purified by flash column chromatography to give 2-(chloromethyl)-5,6-dimethylimidazo[1,2-a]pyridine (1.0 g, yield: 63%). ESI-MS [M+H]+: 195.1.

The synthetic route of 57963-08-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shire Human Genetic Therapies, Inc.; Papaioannou, Nikolaos; Fink, Sarah Jocelyn; Miller, Thomas Allen; Shipps, JR., Gerald Wayne; Travins, Jeremy Mark; Ehmann, David Edward; Rae, Alastair; Ellard, John Mark; (352 pag.)US2019/284182; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 39891-09-3, Adding some certain compound to certain chemical reactions, such as: 39891-09-3, name is 2-Chloropyridine-5-acetonitrile,molecular formula is C7H5ClN2, 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 39891-09-3.

22.0 g (144 mmol) of (6-chloropyridin-3-yl)acetonitrile are added to a mixture of 270 ml of ethanol and 101 ml conc. sulfuric acid, and the mixture is stirred under reflux for 24 h. With stirring, the reaction mixture is then slowly added dropwise to a mixture of 350 g of sodium bicarbonate and 1 liter of water. The aqueous phase is extracted with dichloromethane (five times 400 ml each). The combined organic phases are dried over sodium sulfate, filtered and freed from the solvent using a rotary evaporator. This gives 23.1 g (80% of theory) of the title compound, which is reacted without further purification.1H-NMR (400 MHz, DMSO-d6): delta=8.32 (d, 1H), 7.78 (dd, 1H), 7.49 (d, 1H), 4.10 (q, 2H), 3.77 (s, 2H), 1.19 (t, 3H).LC-MS (Method 3): Rt=1.91 min; MS (ESIpos): m/z=200 [M+H]+.

According to the analysis of related databases, 39891-09-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Thede, Kai; Flamme, Ingo; Oehme, Felix; Ergueden, Jens-Kerim; Stoll, Friederike; Schuhmacher, Joachim; Wild, Hanno; Kolkhof, Peter; Beck, Hartmut; Akbaba, Metin; Jeske, Mario; US2012/264704; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 84487-15-0, Adding some certain compound to certain chemical reactions, such as: 84487-15-0, name is 2-Bromo-5-nitropyridin-4-amine,molecular formula is C5H4BrN3O2, 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 84487-15-0.

A solution of 2-bromo-5-nitropyridin-4-amine (1.5 g, 6.9 mmol) in acetic acid (20 mL) was added in portions into a 75 C suspension of iron powder (1.5 g, 27 mmol) in acetic acid (20 mL). The reaction mixture was stirred at 75 C for 2 h, cooled to room temperature, and filtered through celite. To the filtrate was added 1,3-bis(methoxycarbonyl)-2-methyl-2- thiopseudourea (1.4 g, 6.9 mmol), and the mixture was stirred at 65 C for 60 h. The reaction mixture was cooled to room temperature and concentrated. The solid residue was triturated with dichloromethane and dried to give the title Compound (1.8 g, quantitative yield) as an orange solid. MS (EI) for C8H7BrN4O2: 271/273 (MH+).

According to the analysis of related databases, 84487-15-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EXELIXIS, INC.; ANAND, Neel, Kumar; BLAZEY, Charles, M.; BOWLES, Owen, Joseph; BUHR, Chris, Allen; BUSSENIUS, Joerg; CURTIS, Jeffry, Kimo; DEFINA, Steven, Charles; DUBENKO, Larisa; HARRIS, Jason, R.; JACKSON-UGUETO, Eileen; JOSHI, Anagha; KIM, Angie, Inyoung; TSUHAKI, Amy, Lew; MA, Sunghoon; MANALO, Jean-claire, Limun; NG, Stephanie; PETO, Csaba, J.; RICE Kenneth D.; TSANG, Tsze, H.; ZAHARIA, Cristiana, A.; WO2010/135524; (2010); 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 722550-01-8, name is 4-(Pyrrolidin-1-yl)pyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C9H13N3

General procedure: Compound 2-(4,5-dichloro-2-methoxyphenyl)-7-(pyrrolidin-1-yl)imidazo[1,2-a]pyridine 88 was prepared in the same manner as 2-(5-chloro-2,4-dimethoxyphenyl)-7-(pyrrolidin-1-yl)imidazo[1,2-a]pyridine 5a. The resulting hydrobromic acid salt was neutralized with dilute aqueous ammonia to obtain free base and as an off-white solid (48 rng, 72%). 1H NMR (400 MHz, CDC13): delta 8.48 (s. 1H), 7.87 (s, 1H), 7.85 (d, J = 7.6 Hz, 1H), 7.02 (s, 1H ), 6.42 (br s, 1H), 6,36 (dd, 1H, J= 2.4 Hz, 7.5), 3.97 (s, 3H), 3,38-3.33 (m, 4H), 2.07-2.03 (m, 4H); HPLC (Method 1) 99,73% (AUC), tR = 1 1,76 min.; APCI MS m/z 362 [ M + H ]+

With the rapid development of chemical substances, we look forward to future research findings about 722550-01-8.

Reference:
Patent; ONCOTHERAPY SCIENCE, INC.; MATSUO, Yo; HISADA, Shoji; NAKAMURA, Yusuke; CHAKRABARTI, Anjan; RAWAT, Manish; RAI, Sanjay; SATYANARAYANA, Arvapalli, Venkata; DUAN, Zhiyong; TALUKDAR, Arindam; RAVULA, Srinivas; DECORNEZ, Helene; (491 pag.)WO2017/58503; (2017); 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.785762-99-4, name is 2-(5-(Trifluoromethyl)pyridin-2-yl)acetic acid, molecular formula is C8H6F3NO2, molecular weight is 205.134, as common compound, the synthetic route is as follows.category: pyridine-derivatives

(6) To a 250 ml single-mouth bottle, 15.8 g (0.282 mol, 1.0 eq) of potassium hydroxide was added.Water 54 ml (1 v / w), stir and dissolve. Compound 785762-99-4 54g (0.282 mol, 1.0 eq) was added to the system and stirred to dissolve. After stirring at 40 C for 1 h, the reaction solution was concentrated. A pale yellow solid powder of 61 g was obtained in a yield of 89%. The nuclear magnetic data is as follows:

At the same time, in my other blogs, there are other synthetic methods of this type of compound,785762-99-4, 2-(5-(Trifluoromethyl)pyridin-2-yl)acetic acid, and friends who are interested can also refer to it.

Reference:
Patent; Hunan Huateng Pharmaceutical Co., Ltd.; Chen Min; (6 pag.)CN108997202; (2018); A;,
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. 89364-04-5, name is 3-Bromo-4-nitropyridine, the common compound, a new synthetic route is introduced below. category: pyridine-derivatives

Example 1 (0052) Non-radioactive fluorination of 3-bromo-4-nitropyridine (3): 10 muL of 1 M tetrabutylammonium fluoride (TBAF) solution in THF (10 mumol, 0.5 eq.) was added to a solution of 3-bromo-4-nitropyridine (96%, Aurum Pharmatech, LLC) (20 mumol, 1 eq.) in 500 L of anhydrous dimethylsulfoxide (DMSO) in a 2 mL HPLC vial. The reaction was analyzed by HPLC (conditions A). Retention times: 3-bromo-4-nitropyridine (3)=10.83 min, 3-fluoro-4-nitropyridine=8.38, 3-bromo-4-fluoropyridine (6)=11.76 min. Retention times for the product matched within 0.05 min the reference standard. Identity of the product was confirmed by HR-MS (m/z M+ exp.: 174.9423, calc: 174.9433) and 1H, 13C and 19F NMR. Product amount was calculated from the area under the curve of the HPLC UV1 trace using a calibration curve.

The synthetic route of 89364-04-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The University of Chicago; Brugarolas, Pedro; (35 pag.)US2017/355648; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem