Pyridine-derivatives

Application of 66909-30-6, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 66909-30-6 as follows.

6-(4-(2-Chloro-5-methylnicotinamido)benzoyl)-W-(2-fluoro-6-methylphenyl)-5,6-di hydro-4H-benzo[i)]thieno[2,3-c ]azepine-2-carboxamide; Intermediate (Ilia). Oxalyl chloride (133 mL, 1.58 mol) was added to a suspension of 2-chloro-5-methyl nicotinic acid (225.4 g, 1.313 mol) in DCM (2254 mL) at 18-25C followed by DMF (0.8 mL, 0.010 mol) (results in mild exotherm and gas evolution) and the reaction stirred at 20-25C for 1 hr. HPLC analysis of an aliquot (quenched into methanol) indicated <1 % of 2-chloro-5- methylnicotinic acid was remaining. The solvent was removed in vacuo and the oily residue was azeotroped with DCM (500 mL) to remove residual oxalyl chloride. The resulting oil was taken up into DCM (413 mL) and was added dropwise over 10 min to a suspension of 6-(4-aminobenzoyl)-/V-(2-fluoro-6-methylphenyl)-5,6-dihydro-4/-/-benzo[ 5] thieno[2,3-d]azepine-2-carboxamide (412.9 g, 0.876 mol) in a mixture of pyridine (283 mL, 3.502 mol) and DCM (28920 mL) whilst maintaining the internal temp <40C (maximum temp reached 38C). The reaction was stirred at 18-25C for 1 hr after which time HPLC (sample quenched into methanol) indicated the reaction was complete (<1 % of aniline s/m remaining). Heptane (3300 mL) was added to the mixture at 18-25C and the resulting suspension was stirred for 15 min and the solids then collected by filtration. The filter cake was washed with heptane (2 x 1650 mL) and the crude solid so obtained was slurried in water (4130 mL) at 90- 95C for 30 min and then cooled to 18-25C.The solids were collected by filtration, washed with water (2 x 826 mL) and dried in a vacuum oven at 50C to give the title compound as a white solid (504.2 g, 92% active yield, HPLC purity [230 nm] 98.24%; containing 0.3% pyridine HCI by 1 H NMR and 0.4%. H20 by KF); R< 12.19 min; m/z 625.6 (M+H)+ (ES+). These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,66909-30-6, its application will become more common. Reference:
Patent; PULMOCIDE LIMITED; HUNT, Simon Fraser; ONIONS, Stuart Thomas; SHERBUKHIN, Vladimir; FORDYCE, Euan Alexander Fraser; MURRAY, Peter John; BROOKES, Daniel William; ITO, Kazuhiro; STRONG, Peter; (51 pag.)WO2016/55791; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 15862-37-0, 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. 15862-37-0, name is 2,5-Dibromo-3-nitropyridine, molecular formula is C5H2Br2N2O2, 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.

B. (7-BROMO-PYRIDO [3, 2-D] PYRIMIDIN-4-YL-4-TERT-BUTYL-ISOXAZOLE)-AMINE (COMPOUND 2) 1. 5-bromo-3-nitropyridine-2-carbonitrile Heat a solution of 2, 5-dibromo-3-nitropyridine (1.77g, 6.3 mmol; Malinowski (1988) Bull. Soc. Chim. Belg 97 : 51 ; see also US 5, 801, 183) and cuprous cyanide (0.60 g, 6.69 mmol) in N, N-dimethylacetamide (25 mL) at 100C for 72 hours. After cooling, dilute the mixture with water (25 mL) and extract twice with EtOAc (25 mL each), then wash twice with water (25 mL each). The combined EtOAc extracts are dried (Na2SO4), evaporated, and purified by flash chromatography (50% EtOAc-hexane) to obtain 5-bromo-3-nitropyridine-2- carbonitrile as a pale solid.

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 15862-37-0, 2,5-Dibromo-3-nitropyridine.

Reference:
Patent; NEUROGEN CORPORATION; WO2005/42498; (2005); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 909036-46-0, 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 909036-46-0, name is 2-Chloro-3-iodopyridin-4-amine. This compound has unique chemical properties. The synthetic route is as follows.

Into a 250 mL round bottom flask was placed the 2-chloro-3-iodo-4-aminopyridine (3.0 g, 11.8 mmol), thiophenol (1.3 g, 11.8 mmol), copper(I) iodide (0.11 g, 0.58 mmol), ethylene glycol (1.5 g, 24 mmol) and potassium carbonate (3.3 g, 24 mol). 100 mL of 2-propanol was then added to the reaction mixture and the mixture was heated at reflux for 18 h. The reaction mixture was cooled to room temperature and was filtered under vacuum. The filtrate was diluted with 200 mL of water then was extracted two times with 150 mL of ethyl acetate. The extracts were dried over magnesium sulfate then were filtered and stripped under vacuum. The product was purified using Silica gel chromatography with 2-15% ethyl acetate/dichloromethane as the mobile phase. 2.0 g (72% yield of product was collected.

According to the analysis of related databases, 909036-46-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Universal Display Corporation; Rayabarapu, Dinesh; Xia, Chuanjun; Kwong, Raymond; Ma, Bin; Yeager, Walter; Alleyne, Bert; (82 pag.)CN102449107; (2016); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 885276-93-7, 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. 885276-93-7, name is Ethyl 5-bromopyrazolo[1,5-a]pyridine-3-carboxylate, molecular formula is C10H9BrN2O2, 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: These were made by decarboxylation/Vilsmeier or hydrolysis/reduction/reoxidation as detailed below, unless otherwise stated.Decarboxylation was carried out by refluxing a solution of the ester (1 equiv) in 40% aqueous H2SO4 (3 mL) for 18 h. The solution was then cooled in ice and neutralised to pH 7 with 6 M NaOH, then extracted twice with CH2Cl2. The combined extracts were dried (Na2SO4) and the solvent removed in vacuo to leave the decarboxylated material. The pyrazolo[1,5-a]pyridine was then reacted under Vilsmeier conditions in dry DMF (2 mL) with POCl3 (3 equiv) at 0 C under an atmosphere of N2. The reaction mixture was then warmed to room temperature and stirred for 2 h. The solution was poured onto ice, basified to pH 10 with 1 M NaOH, stirred for 1 h then extracted twice with CH2Cl2. The combined extracts were washed twice with water, dried (Na2SO4) and the solvent removed in vacuo to leave the aldehyde.Alternatively, the ester was hydrolysed by refluxing a solution of the ester (1 equiv) in 1 M NaOH (3 equiv) and EtOH (5 mL) for 6 h. The EtOH was removed in vacuo, and then the aqueous residue acidified to pH 1 with 1 M HCl. The precipitated carboxylic acid was filtered off, washed with water and dried. The carboxylic acid was reduced by adding CDI (1.5 equiv) to a suspension of carboxylic acid (1 equiv) in dry THF (10 mL) under an atmosphere of N2. After stirring for 18 h, the resulting solution was added dropwise to a solution of NaBH4 (5 equiv) in H2O (10 mL) and stirred for 30 min. The reaction was then quenched by the addition of 1 M HCl and stirred for a further 30 min. The solution was neutralised with saturated aqueous NaHCO3 and extracted twice with CH2Cl2. The combined organic layers were dried (Na2SO4) and the solvent removed in vacuo. Chromatography (eluting with a hexanes: EtOAc gradient) gave the alcohol. Reoxidation was carried out by stirring a suspension of the pyrazolo[1,5-a]pyridine-3-methanol (1 equiv) and MnO2 (10 equiv) in CH2Cl2 (2 mL) at room temperature for 4 days. The reaction mixture was then filtered through celite, washed with CH2Cl2, and the solvent removed from the filtrate in vacuo to leave the aldehyde.

According to the analysis of related databases, 885276-93-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kendall, Jackie D.; O’Connor, Patrick D.; Marshall, Andrew J.; Frederick, Raphael; Marshall, Elaine S.; Lill, Claire L.; Lee, Woo-Jeong; Kolekar, Sharada; Chao, Mindy; Malik, Alisha; Yu, Shuqiao; Chaussade, Claire; Buchanan, Christina; Rewcastle, Gordon W.; Baguley, Bruce C.; Flanagan, Jack U.; Jamieson, Stephen M.F.; Denny, William A.; Shepherd, Peter R.; Bioorganic and Medicinal Chemistry; vol. 20; 1; (2012); p. 69 – 85;,
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. 866319-00-8, name is 5-Fluoro-1H-pyrrolo[2,3-b]pyridine. A new synthetic method of this compound is introduced below., Product Details of 866319-00-8

Dissolve 5-fluoro-1H-pyrrole-[2,3-b]pyridine (35.00 g, 257·1 mmol, 1.0 equiv.) in 200 ml DMF, cool to 0 C, add NaH (60 Wt) in portions. % in mineral oil, 10.80 g, 270.0 mmol, 1.05 equiv.), reacted for 30 min, added triisopropylchlorosilane (54.53 g, 282.8 mmol, 1.1 eq.).After reacting at 0 C for 2 hours, TLC showed the reaction was completed. Quenched by adding 50 ml of water, the system was poured into 1 L of water, 1 L of petroleum ether was added, and the mixture was separated and filtered with silica gel. The mother liquid was concentrated to give 82.10 g of a crude yellow oil.

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, 866319-00-8, 5-Fluoro-1H-pyrrolo[2,3-b]pyridine.

Reference:
Patent; Nanjing He Ju Pharmaceutical Co., Ltd.; Pan Guojun; (7 pag.)CN110016030; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 59-26-7, Adding some certain compound to certain chemical reactions, such as: 59-26-7, name is N,N-Diethylnicotinamide,molecular formula is C10H14N2O, 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 59-26-7.

CoSO4·7H2O (0.005 mol, 1.41 g) and DENA (0.01 mol, 1.78 g) in separate beakers were dissolved in 50 mL of distilled water. The solutions of DENA and sodium 4-cyanobenzoate were added to the CoSO4 solution, respectively. The resulting clear solution was allowed to crystallize at room temperature. Pink single crystals were obtained after 1 week. The crystals were filtered off and washed with distilled water and dried at room temperature. Anal. Calcd. (%) for complex 1, C36H40CoN6O8 (MW = 743.68) C, 56.92;H, 5.10; N, 10.95. Found (%): C, 58.15; H, 5.34; N, 11.35. Yield 3.12 g (83.9%).

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. 59-26-7, N,N-Diethylnicotinamide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Sertcelik, Mustafa; Oezbek, Fuereya Elif; Yueksek, Mustafa; Elmal?, Ayhan; Aydo?du, Oemer; Necefo?lu, Hacali; Hoekelek, Tuncer; Chemical Papers; (2020);,
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.1008-91-9, name is 1-(Pyridin-4-yl)piperazine, molecular formula is C9H13N3, molecular weight is 163.22, as common compound, the synthetic route is as follows.Recommanded Product: 1008-91-9

General procedure: To the stirred solution of 6 (0.29 g, 0.001 mol) in dry THF, HOBt (0.16 g, 0.012 mol) and EDCI*HCl (0.23 g, 0.012 mol) were added and continued stirring for 30 min. To the reaction mixture, substituted phenylpiperazine (0.001 mol) was added under ice cold temperature and the reaction mixture was further stirred at room temperature for 6 h. After completion of reaction as monitored byTLC, solvent was evaporated under vacuum. Reaction mixture was extracted with ethyl acetate (2 x 20 mL), collected organic layer was dried over anhydrous Na2SO4, concentrated under vacuum and passed through small bed of silica gel (60e120) using mobile phase (ethyl acetate:hexane; 3:7) to obtain analytically pure final product 7.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1008-91-9, 1-(Pyridin-4-yl)piperazine, and friends who are interested can also refer to it.

Reference:
Article; Penta, Ashok; Franzblau, Scott; Wan, Baojie; Murugesan, Sankaranarayanan; European Journal of Medicinal Chemistry; vol. 105; (2015); p. 238 – 244;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1658-42-0, 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.1658-42-0, name is Methyl 2-(pyridin-2-yl)acetate, molecular formula is C8H9NO2, molecular weight is 151.16, as common compound, the synthetic route is as follows.

Hydrazine (4.15 mL, 132 mmol) was added to a ethanol (66 mL) solution of methyl 2-(pyridin-2-yi)acetate (10 g, 66.2 mmol) at r.t. The mixture was heated and stirred at 85 C for 4 h, and then cooled to r.t. White solid was formed upon standing, which was collected via filtration and used in next step without further purification. LCMS calculated for CTHJ ONSO (M+H)+: 152.1. Found: 152.0.

The chemical industry reduces the impact on the environment during synthesis 1658-42-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; INCYTE CORPORATION; WANG, Xiaozhao; GAN, Pei; HAN, Heeoon; HUANG, Taisheng; MCCAMMANT, Matthew S.; QI, Chao; QIAN, Ding-Quan; WU, Liangxing; YAO, Wenqing; YU, Zhiyong; ZHANG, Fenglei; (284 pag.)WO2019/168847; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1034667-22-5, 5-Fluoro-1H-pyrazolo[3,4-b]pyridin-3-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, Quality Control of 5-Fluoro-1H-pyrazolo[3,4-b]pyridin-3-amine, blongs to pyridine-derivatives compound. Quality Control of 5-Fluoro-1H-pyrazolo[3,4-b]pyridin-3-amine

Example 5A 5-Fluoro-3-iodo-1H-pyrazolo[3,4-b]pyridine [0592] 5-fluoro-1H-pyrazolo[3,4-b]pyridine-3-amine were initially charged in THF (329 ml), and the mixture was cooled to 0 C. 16.65 ml (131.46 mmol) of boron trifluoride diethyl ether complex were then added slowly. The reaction mixture was cooled further to -10 C. A solution of 10.01 g (85.45 mmol) of isopentyl nitrite in THF (24.39 ml) was then added slowly, and the mixture was stirred for a further 30 min. The mixture was diluted with cold diethyl ether (329 ml) and the resulting solid was isolated by filtration. The diazonium salt thus prepared was added a little at a time to a solution at 0 C. of 12.81 g (85.45 mmol) of sodium iodide in acetone (329 ml), and the mixture was stirred at RT for 30 min. The reaction mixture was poured into ice-water (1.8 l) and extracted twice with ethyl acetate (487 ml each time). The collected organic phases were washed with saturated aqueous sodium chloride solution (244 ml), dried, filtered and concentrated. This gave 12.1 g (86% pure, 60% of theory) of the desired compound as a brown solid. The crude product was converted without further purification. [0594] LC-MS (Method 1): Rt=1.68 min; MS (ESIpos): m/z=264 (M+H)+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1034667-22-5, 5-Fluoro-1H-pyrazolo[3,4-b]pyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; Follmann, Markus; Stasch, Johannes-Peter; Redlich, Gorden; Griebenow, Nils; Lang, Dieter; Wunder, Frank; US2014/228366; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 607373-82-0, 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.607373-82-0, name is 4-Methoxy-5-nitropyridin-2(1H)-one, molecular formula is C6H6N2O4, molecular weight is 170.12, as common compound, the synthetic route is as follows.

Example 2 Preparation of 2-chloro-4-methoxy-5-nitro pyridine Charged 2-hydroxy-4-methoxy-5-nitro pyridine (100 g) and dimethylaniline (92 mL) at 10 C.- to 20 C. Added phosphorus oxychloride (300 mL) slowly at 10 C. to 20 C. Refluxed for 2.0 hrs. Cooled to room temperature and dumped reaction mixture in ice and extracted in ethyl acetate after adjusting the pH to around 10 to 12. Treated the organic layer with brine solution and dried over sodium sulphate. Distilled off under reduced pressure to give residue which on crystallisation with diisopropyl ether gave 2-chloro-4-methoxy-5-nitro pyridine (70.0 g).

The chemical industry reduces the impact on the environment during synthesis 607373-82-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Apicore US LLC; Kovi, Ravishanker; Kannapan, Jayaraman; Thakor, Sanjay F.; Naik, Ashish; US2015/315149; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem