Pyridine-derivatives

Electric Literature of 769-28-8, 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.769-28-8, name is 4,6-Dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile, molecular formula is C8H8N2O, molecular weight is 148.16, as common compound, the synthetic route is as follows.

Palladium on carbon (10%) (3.24 g) was charged into a 2 L dry Parr bottle and asmall amount of acetic acid was added. Next added 4,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (30 g, 202.7 mmol), sodium acetate (30.75 g, 375.0 mmol),platinum oxide (0.218 g), and acetic acid (1 L) .. The bottle was capped, placed on Parrapparatus, and shaken under an atmosphere ofH2 (100 psi) for 2 days. The reaction mixture was filtered. The solvent was removed to give a residue, which was treated with150 mL of cone. HCl, and the formed solids were filtered. The yellow filtrate wasconcentrated. To the crude compound was added 30 mL of cone. HCl and 150 mL EtOH,the contents cooled to 0 C, and stirred at 0 oc for 2h. The formed solids were filtered,washed with cold EtOH, ether, and dried. The product was collected as 36 g. This batchwas combined with other batches prepared on smaller scales and triturated with ether togive 51 g of pure compound. IH NMR (400 MHz, DMSO-d6) 8 ppm 11.85 (br s,l H) 8.13(br s, 3 H) 5.93-6.01 (m, 1 H) 3.72-3.80 (m, 2 H) 2.22 (s, 3 H) 2.16 (s, 3 H).

The chemical industry reduces the impact on the environment during synthesis 769-28-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; GLAXOSMITHKLINE LLC; BURGESS, Joelle, Lorraine; DUQUENNE, Celine; KNIGHT, Steven, David; MILLER, William, Henry; NEWLANDER, Kenneth, Allen; VERMA, Sharad, Kumar; WO2013/173441; (2013); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 69142-64-9, 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 69142-64-9, name is Ethyl 6-aminopicolinate. This compound has unique chemical properties. The synthetic route is as follows.

Step 2. Preparation of ethyl 6-(tert-butoxycarbonylamino)picolinate (79):To a solution of ethyl 6-aminopicolinate 78 (5.5 g, 33 mmol) in £-BuOH (120 mL) and acetone (40 mL) was added 4-dimethylaminopyridine (0.08g, 0.66 mmol) and di-tert-butyl dicarbonate (10.8 g, 49.5 mmol). The reaction mixture was stirred at room temperature for 18 h. The solvent was removed by concentration under reduced pressure and a mixture of hexane/dichloromethane (180 mL, 3:1) was added. The resulting mixture was cooled to -20 0C for 2 h. The resulting solids were collected by filtration and dried to afford 79 (11.O g, 91 % yield).

According to the analysis of related databases, 69142-64-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SIRTRIS PHARMACEUTICALS, INC.; OALMANN, Christopher; PERNI, Robert, B.; VU, Chi, B.; WO2010/37127; (2010); A1;,
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. 181123-11-5, name is 5-Chloro-2-cyano-3-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C6H2ClN3O2

Step 1: 3-Amino-5-chloropicolinamide To a suspension of 5-chloro-2-cyano-3-nitropyridine (1.274 mL, 10.9 mmol) in water (22 mL) was added 28% aqueous ammonium hydroxide (3.94 mL, 28.3 mmol), and the reaction was stirred at RT for 20 minutes. Sodium hydrosulfite (2.68 mL, 32.7 mmol) was added, and the reaction mixture was stirred at RT for 70 minutes. The yellow precipitate was collected by vacuum filtration to provide the title compound (1.097 g, 6.39 mmol) as yellow solid. 1H-NMR (400 MHz, DMSO-d6): delta 7.88 (br. s, 1H), delta 7.73 (s, 1H), delta 7.39 (br. s, 1H), delta 7.23 (s, 1H), delta 7.06 (br. s, 2H). LC/MS (ESI+) m/z=172 (M+H).

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, 181123-11-5, 5-Chloro-2-cyano-3-nitropyridine.

Reference:
Patent; MINATTI, Ana Elena; LOW, Jonathan D.; ALLEN, Jennifer R.; CHEN, Jian; CHEN, Ning; CHENG, Yuan; JUDD, Ted; LIU, Qingyian; LOPEZ, Patricia; QIAN, Wenyuan; RUMFELT, Shannon; RZASA, Robert M.; TAMAYO, Nuria A.; XUE, Qiufen; YANG, Bryant; ZHONG, Wenge; US2014/249104; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 16179-97-8 ,Some common heterocyclic compound, 16179-97-8, molecular formula is C7H8ClNO2, 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.

A suspension of 2-pyridineacetic acid hydrochloride (Aldrich; 1.74 g, 10 mmol) and carbonyl diimidazole (1.95 g, 12 mmol) in anhydrous THF (20 mL) was stirred at rt for 1 h. To the mixture was added solid 4-chloroaniline (1.28 g, 10 mmol). After stirring overnight, the solvent was removed and the residue was partitioned between water and EtOAc. The organic layer was dried over Na2SO4 and evaporated to dryness. The crude product was recrystallized from 20 mL of toluene affording 1.5 g (60%) of the amide as a solid. TOF MS ES+ m/z 247 (MH+), 269 (M+Na+).

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. 16179-97-8, 2-(Pyridin-2-yl)acetic acid hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hogenkamp, Derk J.; Johnstone, Timothy B.C.; Gee, Kelvin W.; US2006/293329; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1121-76-2 , The common heterocyclic compound, 1121-76-2, name is 4-Chloropyridine 1-oxide, molecular formula is C5H4ClNO, 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.

A mixture of 4-chloropyridine, 1 -oxide (0.0025 mol), Pd2(dba)3 (catalytic quantity), Xantphos (catalytic quantity) and Cs2CO3 (0.973 g) in dioxane (5ml) was degassed by applying alternating N2 atmosphere and vacuum. Intermediate (70) (0.0023 mol) in dioxane (15ml) was added under N2-atmosphere. The reaction mixture was stirred at 1000C for 2 hours. The mixture was extracted (DCM/H2O), dried, filtered and evaporated. The residue was used crude, yielding intermediate (71).

The synthetic route of 1121-76-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; WO2008/3665; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 884495-03-8, 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. 884495-03-8, name is 3-Amino-2-bromo-5-fluoropyridine. A new synthetic method of this compound is introduced below.

Ethynyltrimethylsilane (0.82 mL, 6.3 mmol) was added dropwise to a stirred mixture of 2-bromo-5-fluoropyridin-3-amine (1.0 g, 5.23 mmol), Pd(PPh3)2Cl2 (0.18 g, 0.26 mmol) and Cul (50 mg, 0.26 mmol) in triethylamine (15 mL) at 0C. The reaction was stirred for 4 h at rt under nitrogen. The mixture was concentrated under reduce pressure. The residue was purified by silica gel column chromatography (PE/EA, from 20/1 tolO/1) to give compound 23 (0.8 g, 73% yield). LC-MS: 209.16 (M+H), Ci0Hi3FN2Si. 1H NMR (CDC13, 400 MHz) 0: 7.83 (s, 1H), 6.75-6.72 (m, 1H), 4.40 (br, 2H), 0.28 (s, 9H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,884495-03-8, 3-Amino-2-bromo-5-fluoropyridine, 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

Adding a certain compound to certain chemical reactions, such as: 16867-03-1, 2-Amino-3-hydroxypyridine, 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, Formula: C5H6N2O, blongs to pyridine-derivatives compound. Formula: C5H6N2O

EXAMPLE 59 2-Ethyloxazolo [4,5-b]pyridine A mixture of 4.4 g. of 2-amino-3-hydroxypyridine, 10.4 g. of propionic anhydride and 15 g. of polyphosphoric acid was heated at 168 C. for 15 minutes. The reaction mixture was cooled slightly and poured into ice water and stirred until the polyphosphoric acid had decomposed. The solution was made alkaline with solid sodium bicarbonate and extracted with 150 ml. of methylene chloride. The dried methylene chloride solution was concentrated to dryness and the residue was dissolved in ether and filtered through aluminum oxide. From the ether filtrate there was obtained 1.2 g. of 2-ethyloxazolo[4,5-b]pyridine, m.p. 52-53 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,16867-03-1, 2-Amino-3-hydroxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; Merck & Co., Inc.; US4038396; (1977); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 123846-66-2, Adding some certain compound to certain chemical reactions, such as: 123846-66-2, name is 2-(5-Nitro-2-pyridinyl)acetonitrile,molecular formula is C7H5N3O2, 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 123846-66-2.

Sodium hydride (67.44 mmol) was added to a solution of 2-(5-nitropyridine-2-yl) acetonitrile (30.65 mmol) in dry THF (250 ml) at 0 C and the reaction mixture was stirred for 0.5 h. Methyl iodide (91.95 mmol) was added to the reaction mixture and reaction mixture was warmed to RT, stirred for another 24 h. Solvent was removed under vacuum; crude product was purified (silica gel column, EtOAc/hexane as eluent) to obtain the title compound. .H NMR (300 MHz, DMSO-d6): delta 9.43 (d, J=2.7 Hz, 1H), 8.55 (dd, J=8.7, 2.4 Hz, 1H), 7.86 (d, J = 8.7 Hz, 1H), 1.82 (s, 6H); MS (m/z): 192 (M+l)+.

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. 123846-66-2, 2-(5-Nitro-2-pyridinyl)acetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PIRAMAL LIFE SCIENCES LIMITED; KUMAR, Sanjay; SHARMA, Rajiv; ZAHLER, Robert; SAHU, Bichismita; AGARWAL, Veena, R.; NAIK, Nishigandha; WO2012/7926; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1235865-75-4, 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. 1235865-75-4, name is Methyl 2-((1H-pyrrolo[2,3-b]pyridin-5-yl)oxy)-4-fluorobenzoate. A new synthetic method of this compound is introduced below.

In 100mL2-Boc-octahydropyrrolyl [3,4-c] pyrrole (0.73 g, 3.4 mmol), 2-((1H-pyrrolo [2,3-b] pyridin-5-yl) oxy) -4-fluorobenzoic acidMethyl ester (1.00 g, 3.8 mmol), dipotassium hydrogen phosphate(2.28 g, 10 mmol) and 40 mL of DMSO were reacted at 130 C. for 6 h, cooled to room temperature, 50 mL of water and 30 mLEA, the layers were separated, the aqueous layer was extracted twice with 50 mL of EA, the combined organic phases were washed once with 50 mL of saturated brine,Dried over sodium sulfate, filtered and spin-dried to give 0.702 g of product in 43% yield.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1235865-75-4, Methyl 2-((1H-pyrrolo[2,3-b]pyridin-5-yl)oxy)-4-fluorobenzoate, and friends who are interested can also refer to it.

Reference:
Patent; Sun Yat-sen University; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Kou Yuhui; Hu Bolin; Jiang Haigang; Ye Jiuyong; Liu Zhiqiang; Xie Hongming; Zhang Yingjun; Yan Ming; (39 pag.)CN106749233; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 5418-51-9, 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 5418-51-9 as follows.

Step A: 2-(Difluoromethoxy)-5-nitropyridine To 2-hydroxy-5-nitropyridine (7 g, 50 mmol) in acetonitrile (500 mL) was added sodium sulfate (1.5 g, 10.6 mmol), and 2,2-difluoro-2-(fluorosulfonyl)acetic acid (6.2 mL, 60 mmol) and the reaction was allowed to stir at room temperature for 16 hours. The reaction was quenched with saturated aqueous sodium bicarbonate and the acetonitrile was removed in vacuo. The remaining aqueous component was extracted with ethyl acetate, washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The pale brown oily solid was triturated with ether/hexanes, filtered and the filtrate concentrated to afford 2-(difluoromethoxy)-5-nitropyridine (4.7 g, 24.7 mmol, 49% yield) as a yellow oil. 1H NMR (400 MHz, DMSO-d6) delta ppm 9.14 (d, J=2.76 Hz, 1H), 8.68 (dd, J=9.03, 2.76 Hz, 1H), 7.98 (s, 0.5H), 7.62 (s, 0.5H), 7.34 (d, J=9.03 Hz, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5418-51-9, its application will become more common.

Reference:
Patent; Bristol-Myers Squibb Company; US2009/270405; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem