Pyridine-derivatives

Synthetic Route of 139022-25-6, 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. 139022-25-6, name is Imidazo[1,2-a]pyridine-6-carboxylic acid. A new synthetic method of this compound is introduced below.

A suspension of imidazo[1,2-a]pyridine-6-carboxylic acid (1.0 g), EDCI (1.775 g), HOBt (1.415 g) and N-methylmorpholine (1.0 ml) in DMF (20 ml) and DCM (5 ml) was stirred at 22C for 40 min. The resulting reddish solution was treated with diisopentylamine (1.9 ml) and N-methylmorpholine (1.0 ml) in this order and the reaction mixture was stirred at 22C for 24 h. The mixture was diluted with diethyl ether (100 ml) and washed with saturated sodium bicarbonate solution (2 x 60 ml). The combined aqueous layer was washed with diethyl ether (2 x 50 ml). The combined organic extract was washed with water (100 ml) and brine (100 ml), dried over sodium sulfate, filtered, and evaporated. The crude product was purified by column chromatography.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,139022-25-6, Imidazo[1,2-a]pyridine-6-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; Santhera Pharmaceuticals (Schweiz) AG; EP2168965; (2010); 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.1446237-40-6, name is 5-Bromo-1,4-dimethyl-3-nitropyridin-2(1H)-one, molecular formula is C7H7BrN2O3, molecular weight is 247.05, as common compound, the synthetic route is as follows.category: pyridine-derivatives

To a stirred mixture of NEUCI (17.3 g, 323.42 mmol, 10.0 equiv) in EEO/EtOH (1 /1 , 400 ml_) was added 5-bromo-1 , 4-dimethyl-3-nitro-1 , 2-dihydropyridin-2-one (8.0 g, 32.38 mmol, 1 .0 equiv) and Fe (18.1 g, 324.1 1 mmol, 10.0 equiv) at room temperature. The mixture was stirred at rt. for 2 hours, the solid was filtered off. The filtrate was diluted with water (100 ml_) and extracted with ethyl acetate (200 ml_ x 2). The organic layers were combined and washed with saturated NaCI (aq.), dried over with anhydrous Na2SC>4. After filtration, the filtrate was concentrated under reduced pressure. This resulted in 6.56 g (93%) 3-amino-5-bromo-1 ,4-dimethyl- pyridin-2(1 H)-one as a red solid that was used directly without further purification. LCMS (ESI) m/z: [M+H]+ = 217.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1446237-40-6, 5-Bromo-1,4-dimethyl-3-nitropyridin-2(1H)-one, and friends who are interested can also refer to it.

Reference:
Patent; FOGHORN THERAPEUTICS INC.; ZHOU, Qianhe; BOCKER, Michael; MILLAN, David, Simon; CHAN, Ho, Man; SOARES, Luis; NETHERTON, Matthew, Russell; RUPPEL, Sabine, K.; YANG, Zhaoxia; LOWE, Jason, T.; BRUCELLE, Francois; (220 pag.)WO2019/152440; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1003-68-5, 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 1003-68-5, name is 5-Methylpyridin-2(1H)-one. This compound has unique chemical properties. The synthetic route is as follows.

Sequentially adding to the reaction bottle 5-methyl -2 (1H)-pyridone 109 g, anhydrous potassium carbonate 165 g, cuprous bromide 0.72 g, bromophenylacetic 188.4 g, 1,10-phenan throline 0.9 g and N, N-dimethyl formamide 500 ml, the mixture is heated to 90 C about 2 hours, cooling to the end 25 C, by adding 2000 ml of water mixing, filtering, in the filter cake into the reaction bottle, by adding 5% acetic acid aqueous solution 1500 ml, the temperature is increased to 90 C, filtration, filtrate with 20% sodium hydroxide solution to adjust the pH= 13, and then cooled to the 5 C the following filtering, decompression drying to obtain the pirfenidone 132.5 g, spare.

According to the analysis of related databases, 1003-68-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chongqing Kangle Pharmaceutical Co., Ltd; Tang, Ming; Chen, Wenhui; Chen, Lin; Ma, Xiaoping; Zheng, Xue; Yang, Jibin; Cai, Zhongwen; Wang, Yachuan; (6 pag.)CN105315198; (2016); 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. 87109-10-2, name is 3-Phenylpyridin-2-amine, the common compound, a new synthetic route is introduced below. Formula: C11H10N2

General procedure: To a solution of a2-aminopyridine derivative 2 or 4 (0.9 mmol) in absolute EtOH(5 mL) was added dropwise ethyl 4,4,4-trifluorobutynoate 1 (230 mg, 1.4 mmol). The mixturewas stirred at room temperature for 30 minutes before an additional portion of 1 (150 mg, 0.9 mmol) was added. The reaction mixture was stirred at room temperature untilcompletion of the reaction. The solvent was then evaporated under reducedpressure and the residue was triturated with Et2O (20 mL) andfiltered off to afford the expected pyrido[1,2-a]pyrimidin-2-ones 3.

The synthetic route of 87109-10-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Silpa, Laurence; Niepceron, Alisson; Laurent, Fabrice; Brossier, Fabien; Penichon, Melanie; Enguehard-Gueiffier, Cecile; Abarbri, Mohamed; Silvestre, Anne; Petrignet, Julien; Bioorganic and Medicinal Chemistry Letters; vol. 26; 1; (2016); p. 114 – 120;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 59281-14-0, 5-(Benzyloxy)-2-(hydroxymethyl)pyridin-4(1H)-one, 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, COA of Formula: C13H13NO3, blongs to pyridine-derivatives compound. COA of Formula: C13H13NO3

A. Synthesis of [5-(benzyloxy)-4-isopropoxypyridin-2-yl]methanol (C32). A solution of 5-(benzyloxy)-2-(hydroxymethyl)pyridin-4(1H)-one (prepared by a procedure similar to that reported by M. M. O’Malley et al., Organic Letters 2006, 8, 2651-2652) (1.3 g, 5.6 mmol) in N,N-dimethylformamide (11.2 mL) was treated with 2-iodopropane (95%, 1.77 mL, 16.8 mmol) and potassium carbonate (1.17 g, 8.42 mmol). The slurry was stirred for 2.5 hours at room temperature and then heated at 80 C. for 18 hours, with addition of 2-iodopropane (1.3 mL, 12 mmol) after the first hour. The mixture was extracted three times with ethyl acetate, and the combined organic layers were dried over sodium sulfate. Filtration and removal of solvent in vacuo gave a residue, which was purified by silica gel chromatography (Eluants: 0%, then 20%, then 40% 2-propanol in ethyl acetate) to provide the product as a brown solid. Yield: 700 mg, 2.56 mmol, 46%. 1H NMR (400 MHz, DMSO-d6) delta 8.06 (s, 1H), 7.30-7.44 (m, 5H), 7.06 (s, 1H), 5.28 (t, J=5.9 Hz, 1H), 5.13 (s, 2H), 4.72 (septet, J=6.0 Hz, 1H), 4.42 (d, J=5.9 Hz, 2H), 1.32 (d, J=6.0 Hz, 6H).

The synthetic route of 59281-14-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; Brodney, Michael Aaron; Efremov, Ivan Viktorovich; Helal, Christopher John; O’Neill, Brian Thomas; US2013/150376; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 39621-00-6, 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. 39621-00-6, name is 2,6-Dichloro-4-methylpyridine, molecular formula is C6H5Cl2N, 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.

Nitric acid (1.5 mL, 33.6 mmol) was added to a solution of sulfuric acid (2.5 mL, 46.9 mmol) stirred under nitrogen at 0 C. Then 2,6-dichloro-4-methylpyridine (0.500 g, 3.09 mmol) was added at 0 C. Then the reaction mixture was stirred at 100 C. for 16 hr. The reaction was monitored by TLC. After completion, the reaction mixture was quenched with crushed ice and neutralized with NH4OH solution and filtered the solid and dried under vacuum to give the desired product (0.300 g, 1.443 mmol, 46.8% yield) as a pale yellow solid, LCMS (m/z) 206.8 [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 39621-00-6, 2,6-Dichloro-4-methylpyridine.

Reference:
Patent; BLUM, Charles A.; Caldwell, Richard Dana; Casaubon, Rebecca; Disch, Jeremy S.; Fox, Ryan Michael; Koppetsch, Karsten; Miller, William Henry; NG, Pui Yee; Oalmann, Christopher; Perni, Robert B.; Szczepankiewicz, Bruce G.; White, Brian; US2015/152108; (2015); 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. 1945-84-2, name is 2-Ethynylpyridine. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 1945-84-2

General procedure: To a stirred solution of the glycosyl azide 2 (1 mmol for alkynes 1a,b,c; 2 mmol for 1d) in t-BuOH-H2O (4:1, 100 mL) was added the alkynyl compound 1 (1 mmol), CuSO4·H2O (50 mg, 0.2 mmol for 1a,b,c; 100 mg, 0.4 mmol for 1d), and sodium ascorbate (80 mg, 0.4mmol for 1a,b,c; 160 mg, 0.8 mmol for 1d). The resulting solution was stirred at 40 C until TLC (eluent: see individual examples) showed complete consumption of the starting material (12-48 h). The reaction mixture was diluted with H2O (100 mL) and extracted with CH2Cl2 (3 × 50 mL). The combined organic layers were washed with 1M aq EDTA solution (50 mL) and H2O (50 mL), dried (Na2SO4), filtered,and concentrated. Flash chromatography or crystallization of thecrude product gave compounds 3-6.

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, 1945-84-2, 2-Ethynylpyridine.

Reference:
Article; Kraft, Jochen; Schmollinger, Daniel; Maudrich, Jakob; Ziegler, Thomas; Synthesis; vol. 47; 2; (2015); p. 199 – 208;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 98-98-6, 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 98-98-6, name is Picolinic acid. This compound has unique chemical properties. The synthetic route is as follows.

1) Synthesis of (4-Chloropvridine-2-carboxylic acid)-methvlamide (2) ci I 1. SOC12 CH NH DMF MgClz _ O THF O 2. MeOH N N Toluene 1 60 ml of thionylchloride are heated to 45 C under a N2 atmosphere, and slowly mixed with 1.83 ml dimethyl formamide. To this solution, 20 g of pyridine-2-carboxylic acid are added portion wise. The reaction mixture is stirred for another 15 min at 45 C and subsequently kept at 80 C for 24 hours. The reaction mixture is evaporated to dryness, the residue is stripped several times with water free toluene. The oil obtained by this procedure is dissolved in toluene, chilled to 0 C, slowly mixed with methanol and stirred for 1 hour. The precipitated solid is separated by suction filtration, washed with toluene and recrystallized from acetone. Yield : 15 g (44 %) of 1, colorless crystals

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 98-98-6, Picolinic acid.

Reference:
Patent; MERCK PATENT GMBH; WO2005/58832; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 7169-97-3, 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 7169-97-3, name is N-(5-Bromopyridin-2-yl)acetamide. This compound has unique chemical properties. The synthetic route is as follows.

N-(5-bromopyridin-2-yl)acetamide (4.30 g, 20 mmol),P-carboxyphenylboronic acid(3.66 g, 22 mmol) was added to a 250 ml pear-shaped bottle.Further, cesium carbonate (13.0 g, 40 mmol) and tetrakistriphenylphosphine palladium (1.2 g, 1 mmol) were successively added.Add acetonitrile/water to the above mixture (V:V=3:2)200ml. N2 protection, the oil bath was heated to 90 C for 48 h. After the reaction,The reaction solution was cooled to room temperature and suction filtered.The filtrate was adjusted to pH 4 with 6 mol/L hydrochloric acid, and a white solid was precipitated.The filter cake was vacuum dried to give the product 3.89 g, yield 76%.

According to the analysis of related databases, 7169-97-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Xi’an Jiaotong University; Zhang Jie; Pan Xiaoyan; Liang Liyuan; Lu Wen; Wang Sicen; He Langchong; Si Ru; Wang Jin; (14 pag.)CN109651243; (2019); A;,
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. 98027-84-0, name is 2,6-Dichloro-4-iodopyridine, molecular formula is C5H2Cl2IN, 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. category: pyridine-derivatives

Preparative Example 2,6-Dichloro-4-cyclopropylpyridine Cyclopropylzinc bromide (0.5 M in tetrahydrofuran, 15 mL, 7.3 mmol) was added to a mixture of 2,6-dichloro-4-iodopyridine (1.0 g, 3.65 mmol) and tetrakis(triphenylphosphine)palladium(0) (211 mg, 0.182 mmol) in anhydrous tetrahydrofuran (10 mL) at 0 C. After being stirred at room temperature for 4 hours, the reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (petroleum ether: ethyl acetate = 100: 1) to provide 2,6- dichloro-4-cyclopropylpyridine. MS ESI calc’d. for C8H8C12N [M + H]+ 188, found 188. XH NMR: (400 MHz, CDC13) 5 6.89 (s, 2H), 1.87 – 1.80 (m, 1 H), 1.18 – 1.13 (m, 2H), 0.84 – 0.80 (m, 2H).

With the rapid development of chemical substances, we look forward to future research findings about 98027-84-0.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MERCK CANADA INC.; MACHACEK, Michele, R.; ALTMAN, Michael, D.; ROMEO, Eric, T.; VITHARANA, Dilrukshi; CASH, Brandon; SIU, Tony; ZHOU, Hua; CHRISTOPHER, Matthew; KATTAR, Solomon, D.; HAIDLE, Andrew, M.; CHILDERS, Kaleen Konrad; MADDESS, Matthew, L.; REUTERSHAN, Michael, H.; DUCHARME, Yves; GUERIN, David. J.; SPENCER, Kerrie; BEAULIEU, Christian; TRUONG, Vouy Linh; GUAY, Daniel; NORTHRUP, Alan, B.; TAOKA, Brandon, M.; LIM, Jongwon; FISCHER, Christian; BUTCHER, John, W.; OTTE, Ryan, D.; SUN, Binyuan; WO2013/192125; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem