Pyridine-derivatives

Electric Literature of 960289-03-6 , The common heterocyclic compound, 960289-03-6, name is 2-Bromo-5,6-dihydrothieno[2,3-c]pyridin-7(4H)-one, molecular formula is C7H6BrNOS, 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.

Preparation 29; 2-(4-Chloro-phenyl)-6H-thieno[2,3-c]pyridin-7-one; Combine 2-bromo-6H-thieno[2,3-c]pyridin-7-one (25.0 g, 108.7 mmol), A- chlorophenylboronic acid (18.7 g, 119.5 mmol), sodium carbonate (23.5 g, 217.3 mmol), ethanol (121 mL), 1 ,2-dimethoxyethane (604 mL), and water (121 mL). Purge the mixture with nitrogen for 20 min. Add tetrakis(triphenylphosphine)palladium (3.77 g, 3.26 mmol). Heat the reaction mixture at 85 0C overnight. Allow the reaction to cool to RT. Reduce the reaction solvent volume to half on a rotory evaporator. Filter the mixture with water (2 x 400 mL), ether (400 mL), and ethylacetate (20 mL) and dry the solids in vacuo at 40 0C to give 25.4 g (89%) of the title compound. LC-MS/ES m/z (35Cl) 262.0 [M+H]+.

The synthetic route of 960289-03-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2007/146758; (2007); A2;,
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.71777-70-3, name is Ethyl 4-ethoxypicolinate, molecular formula is C10H13NO3, molecular weight is 195.22, as common compound, the synthetic route is as follows.HPLC of Formula: C10H13NO3

To a solution of ethyl 4-ethoxypicolinate (3.44 g, 17.43 mmol) and 4-methoxy acetophenone (2.62 g, 17.43 mmol) in THF (100 mL) and DMSO (50 mL) was added NaH (1.4 g, 34.80 mmol). The resulting mixture was stirred at 95 C. for 6 h. The reaction mixture was cooled to rt and quenched with water (100 mL). The mixture was extract with EtOAc (3×150 mL) and concentration to a yellow solid. The solid was washed with hexanes to afford the diketone (3.6 g, 69%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,71777-70-3, Ethyl 4-ethoxypicolinate, and friends who are interested can also refer to it.

Reference:
Patent; RVX Therapeutics Inc.; McLure, Kevin G.; Young, Peter R.; US2013/281396; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 89415-54-3, 5-Bromo-N2-methylpyridine-2,3-diamine, 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, 89415-54-3, blongs to pyridine-derivatives compound. Formula: C6H8BrN3

6-Bromo-3-methyl-3H-[1,2,3]triazolo[4,5-b]pyridineTo a solution of 5-bromo-N2-methylpyridine-2,3-diamine (720 mg, 3.56 mmol) inH2S04(1.90 muIota_, 35.6 mmol) at RT, NaN02(246 mg, 3.56 mmol) was added. The reaction mixture was stirred for 1 h after which time water was added to quench the reaction. EtOAc was added, and the layers were separated. The aqueous layer was extracted once with EtOAc, and the combined organic layers were washed once with brine. The organic layer was concentrated to give 694 mg (91 %) of the title compound. LC-MS m/z 212.8, 214.8 (M+H)+, 0.66 (ret. time).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,89415-54-3, its application will become more common.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ASTEX THERAPEUTICS LIMITED; BOEHM, Jeffrey Charles; DAVIES, Thomas Glanmor; WOOLFORD, Alison Jo-anne; GRIFFITHS-JONES, Charlotte Mary; WILLEMS, Hendrika Maria Gerarda; NORTON, David; SAXTY, Gordon; HEIGHTMAN, Thomas Daniel; LI, Tindy; KERNS, Jeffrey K.; DAVIS, Roderick S.; YAN, Hongxing; WO2015/92713; (2015); 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.1190320-33-2, name is 6-Fluoro-1H-pyrrolo[3,2-b]pyridine, molecular formula is C7H5FN2, molecular weight is 136.13, as common compound, the synthetic route is as follows.name: 6-Fluoro-1H-pyrrolo[3,2-b]pyridine

Step 3: l-(6-Fluoro-lH-pyrrolo[3,2-b]pyridin-3-yl)-N,N-dimethylmethanamine (25) 25 [00632] Paraformaldehyde (0.24 g, 8.1 mmol) and dimethylamine hydrochloride (0.66 g, 8.1 mmol) were added to a stirred solution of compound 24 (1.0 g, 7.35 mmol) in n-butanol (10 mL). The reaction was refluxed for 3 h. The solution was allowed to cool to rt and poured into 15% HCl (100 mL). The butanol layer was discarded and the water phase was adjusted to pH13- 14 with 2M NaOH. The resulting mixture was extracted with ethyl acetate (100 mLx3). The organic extracts were combined, washed with brine (100 mL), dried over anhydrous sodium sulfate, and concentrated to give compound 25 (1.0 g, 71% yield), which was used in the next reaction without purification. LC-MS: 194.02 (M+H), Ci0Hi2FN3. 1H NMR (CDC13, 400 MHz) S: 10.13 (br, 1H), 8.36 (s, 1H), 7.31-7.22 (m, 2H), 3.75 (s, 2H), 2.32 (s, 6H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1190320-33-2, 6-Fluoro-1H-pyrrolo[3,2-b]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; AKARNA THERAPEUTICS, LTD.; MOHAN, Raju; PRATT, Benjamin, Anthony; (297 pag.)WO2016/103037; (2016); 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. 7477-10-3, name is 6-Chloro-5-nitronicotinic acid, the common compound, a new synthetic route is introduced below. COA of Formula: C6H3ClN2O4

To a suspension of 49.0 g (0.27 mol) 6-hydroxy-5-nitro-nicouenic acid in thionyl chloride (240 mi) are added 2 ml of DMF. This mixture is stirred at 60°C until the evolution of gaz has ended. Then it is stirred at 80°C for further 18 h. Residual thionyl chloride is removed under vacuo and the resulting residue is coevaporated three times with toluene. Subsequently this reaction mixture is dissolved in dichloromethane (100 mi) and cooled to 0°C before methanol (55.5 ml) is dropwise added. The precipitated solid is filtered off and dried under vacuo at 50°C to give 27.6 g (13.7 mmol/52 percent) of the title compound as a light yellow solid with a melting point of 78°C (dichloromethane/methanol).

The synthetic route of 7477-10-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALTANA PHARMA AG; WO2005/77947; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 165547-79-5, 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 165547-79-5, name is 4-Chloro-3-nitro-2(1H)-pyridinone. This compound has unique chemical properties. The synthetic route is as follows.

Methyl iodide (2.06 ml_, 32.99 mmol) was added to a suspension of 4-chloro-2-hydroxy-3- nitropyridine (prepared as descibed in Bioorg. Med. Chem. Lett, 2003, 13, 125) (2.87 g, 16.49 mmol) and siver carbonate (4.55 g, 16.49 mmol) in toluene (100 ml.) and the mixture heated at 85 C for 3.5 h. On cooling to ambient temperature the mixture was filtered through dicalite and washed with toluene. The combined filtrate and washings were concentrated in vacuo and the crude product purified by chromatography on silica gel with EtOAc:heptane (1 :9, v/v) as eluent. The pure product was collected as a white solid (1.99 g, 64 %). Data for 4-chloro-2-hydroxy-3-nitropyridine: MS (ESI) m/z: 189/191 ([M+H]+).

According to the analysis of related databases, 165547-79-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; N.V. ORGANON; WO2007/39563; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 75358-90-6, 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 75358-90-6, name is Ethyl 2-cyanonicotinate. This compound has unique chemical properties. The synthetic route is as follows.

[0142] To a solution of ethyl 2-cyano-3-pyridinecarboxylate (2.5 g) and cone. HCl (5 mL) in 150 mL ethanol was added 10% Pd/C (wet, 250 mg) and the reaction mixture was hydrogenated using a hydrogen balloon and stirred for 12 h. The reaction was filtered through celite and ethanol was evaporated to give ethyl 2-(aminomethyl)-3- pyridinecarboxylate HCl as a white solid which was used in the next step without further purification.

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 75358-90-6, Ethyl 2-cyanonicotinate.

Reference:
Patent; GLOBAL BLOOD THERAPEUTICS, INC.; CYTOKINETICS, INC.; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; METCALF, Brian; CHUANG, Chihyuan; WARRINGTON, Jeffrey; PAULVANNAN, Kumar; JACOBSON, Matthew P.; HUA, Lan; MORGAN, Bradley; WO2013/102142; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 213193-32-9, Adding some certain compound to certain chemical reactions, such as: 213193-32-9, name is 5-Acetyl-2-methoxypyridine,molecular formula is C8H9NO2, 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 213193-32-9.

2- methoxy-5-acetyl pyridine (1.51 g, 10 mmol) was treated with 6N HCl at 100C for 5 hours. The reaction mixture was neutralized with sodium hydroxide to pH 7 and then extracted several times with DCM. Organic layer was dried over sodium sulfate, evaporated and the residue was crystallized from ethyl acetate to give 5-acetyl-2(lH)- pyridone as a white solid, 1.06 g (78%). This compound (685.7 mg, 5 mmol) was reacted with iodobenzene (0.84 ml, 7.5 mmol) in the presence of CuI (95 mg, 0.5 mmol) and K2CO3 (691 mg, 5 mmol) in DMF (5 ml) at 1350C overnight. The reaction mixture was diluted with 10% ammonia (15 ml) and extracted with ethyl acetate. The organic extract was washed with saturated sodium chloride, dried over magnesium sulfate and evaporated. Column chromatography (10% ethyl acetate-DCM) afforded 407 mg (38%) of the target compound as a white solid. The 1H NMR spectra was consistent with the structure of Compound 16.

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. 213193-32-9, 5-Acetyl-2-methoxypyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; INTERMUNE, INC.; WO2006/122154; (2006); A2;,
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.22280-60-0, name is 6-Chloro-2-methyl-3-nitropyridine, molecular formula is C6H5ClN2O2, molecular weight is 172.57, as common compound, the synthetic route is as follows.name: 6-Chloro-2-methyl-3-nitropyridine

Preparation 6 2-Methoxy-5-Nitro-6-Methylpyridine Sodium metal (8.68 g, 378 mmol) was added to methanol (350 mL) pre-cooled to 0 C. After the sodium completely dissolved, 2-chloro-5-nitro-6-methylpyridine (40.78 g, 236 mmol) was slowly added as a solid. The reaction mixture was heated at reflux temperature overnight, then poured into ice-water. The product was filtered and dried in vacuo overnight to give 29.39 grams of the title compound. (73%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,22280-60-0, 6-Chloro-2-methyl-3-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; Eli Lilly and Company; US6358972; (2002); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 82523-07-7, Adding some certain compound to certain chemical reactions, such as: 82523-07-7, name is Methyl 3H-imidazo[4,5-c]pyridine-6-carboxylate,molecular formula is C8H7N3O2, 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 82523-07-7.

Cooling in the ice bath,5g (28.22mmol) of 3H-imidazo[4,5-c]pyridine-6-carboxylate40mL NaOH aqueous solution (2M) dissolved,After 4 h of reaction, the reaction mixture was adjusted to pH 7 with dilute hydrochloric acid (2M).Allow to stand and allow the solid to be analyzed. Filter, filter and wash with distilled water, dry,Yield 1.757 g (38%) of the title compound.It is a pale yellow solid.

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. 82523-07-7, Methyl 3H-imidazo[4,5-c]pyridine-6-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Capital University of Medical Sciences; Zhao Ming; Peng Shiqi; Wang Yuji; Wu Jianhui; Gui Lin; Wang Yongjian; (13 pag.)CN108976225; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem