Category: pyridine-derivatives

Related Products of 63071-03-4, 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 63071-03-4, name is 2-Methoxy-6-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Example given for n = 7: An oven dried round bottom flask, equipped with magnetic stir bar was sealed under argon. To the flask, THF (10 mL) and n-BuLi (2.4 M in hexanes, 2.0 mL, 4.8 mmol) were added and cooled to 0 oC. To this flask, 2-methoxy-6-methylpyridine (0.50 mL, 4.1 mmol) was added drop wise via syringe, which resulted in a yellow color that intensified to brown over a few min. After 10 min, 1,6-dibromohexane (2.0 mL, 13 mmol) was added in one portion and the color rapidly dissipated. After an additional 2 h, the reaction was quenched upon addition of water. The phases were separated and the aqueous phase was extracted with ethyl acetate. The combined organic phases were washed with brine, dried (MgSO4) and concentrated in vacuo. Final purification by column chromatography (0% -15% ethyl acetate in hexanes) afforded the desired compound (397 mg, 34%) along with the dimer 1,8-bis(6-methoxypyridin-2-yl)octane (180 mg, 27%).

According to the analysis of related databases, 63071-03-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Topczewski, Joseph J.; Lodge, Alexander M.; Yasapala, Sumana N.; Payne, Maurice K.; Keshavarzi, Pedrom M.; Quinn, Daniel M.; Bioorganic and Medicinal Chemistry Letters; vol. 23; 21; (2013); p. 5786 – 5789;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 155377-05-2 , The common heterocyclic compound, 155377-05-2, name is Methyl 6-(trifluoromethyl)picolinate, molecular formula is C8H6F3NO2, 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.

The biuret (13 g, 126.3 mmol) was dissolved in 300 mL of ethylene glycol dimethyl ether, sodium hydride (42 g, 1053 mmol) was added portionwise, and stirred at 50 C for 1 h. Methyl 6-(trifluoromethyl)-picolinate (21.6 g, 105.3 mmol) was added and the mixture was heated at 85 C for 16 h. The reaction solution was poured into water, the pH was adjusted with concentrated hydrochloric acid, filtered, and then filtered to give the title compound.

The synthetic route of 155377-05-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nanjing Shenghe Pharmaceutical Co., Ltd.; Zhao Liwen; Zhang Jin; Chen Cheng; Xu Chenglong; Wang Cheng; (21 pag.)CN110054617; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 136888-20-5, 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. 136888-20-5, name is 5-Fluoro-3-nitropyridin-2(1H)-one, molecular formula is C5H3FN2O3, 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.

PREPARATION 53 2-Chloro-5-fluoro-3-nitropyridine 5-Fluoro-3-nitro-pyridin-2-ol (1.00 g, 5.33 mmol) was dissolved in acetonitrile (40 mL) and tetraethylammonium chloride (2.10g, 12.65 mmol) was added. The mixture became clear, phosphorous oxytrichloride (1.94 g, 12.65 mmol) was added at room temperature and the mixture was heated at 90 oC for 24h. The reaction mixture was evaporated to dryness; the residue was taken up with water (100 mL) and extracted with ethyl acetate (2×100 mL). The organic layer was dried with sodium sulfate, filtered and evaporated to dryness. A yellow solid (0.90 g, 69%) was isolated, pure enough to perform the next synthetic step. LRMS (m/z): 177 (M+1)+

According to the analysis of related databases, 136888-20-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Almirall, S.A.; EP2518071; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 13466-43-8, 3-Bromopyridin-2(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, Quality Control of 3-Bromopyridin-2(1H)-one, blongs to pyridine-derivatives compound. Quality Control of 3-Bromopyridin-2(1H)-one

(c) 3-Bromo-2-methoxypyridine Under an argon atmosphere, a mixture of 3-bromo-2-hydroxypyridine (3.49 g, 20 mmol), silver carbonate (3.67 g, 13.31 mmol), and iodomethane (1.5 mL, 24.1 mmol) in benzene (30 mL) was stirred in the dark at 40 C. to 50 C. for 24 hours, cooled in an ice bath, and filtered. The filtrate was washed once with 2% aqueous sodium bicarbonate and twice with water, dried (MgSO4), the benzene was evaporated at atmospheric pressure, and the residue was purified by flash chromatography (eluding with hexane/ethyl acetate, 2:1) to obtain the title compound (2.35 g, 12.5 mmol, 62%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13466-43-8, 3-Bromopyridin-2(1H)-one, and friends who are interested can also refer to it.

Reference:
Patent; Astra Aktiebolag; US6110914; (2000); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 17228-63-6, 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. 17228-63-6, name is 6-Chloro-1-methylpyridin-2(1H)-one. A new synthetic method of this compound is introduced below.

General procedure: This compound was prepared using a method analogousto that of Example 102 (intermediate 102.1 ), intermediate96.1 replacing 2,6-difluoropyridine except that the reactionmixture was stirred for 2 days at 85 C LC-MS (B): tR=0.52 min; [M+H]+: 280.30

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,17228-63-6, its application will become more common.

Reference:
Patent; Actelion Pharmaceuticals Ltd.; Hilpert, Kurt; Hubler, Francis; Murphy, Mark; Renneberg, Dorte; US2014/73651; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 779345-37-8, 5-Fluoro-2-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, Formula: C5H3FN2O2, blongs to pyridine-derivatives compound. Formula: C5H3FN2O2

Preparation 104-(6-Nitro-pyridin-3-yloxy)-piperidine-1-carboxylic acid tert-butyl esterAdd potassium tert-butoxide (4.84 g) to a solution of tert-butyl 4-hydroxy-1-piperidine-carboxylate (8.76 g) in dimethylacetamide (DMA, 39 mL) at 0 C. under nitrogen. Stir for 1 h and add drop wise a solution 5-fluoro-2-nitro-pyridine (5 g) in DMA (78 mL). Let the reaction stir at RT overnight. Add water and stand for 1 h. Filter, wash with water. Purify by silica gel column chromatography eluting with DCM/EA (0-15%) to afford 5.65 g of the title compound. MS (ES+): m/z=324 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,779345-37-8, 5-Fluoro-2-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; COATES, David A.; GELBERT, Lawrence Mark; KNOBELOCH, John M.; DE DIOS MAGANA, Alfonso; DE PRADO GONZALEZ, Ana; FILADELFA DEL PRADO CATALINA, Miriam; GARCIA PAREDES, Maria Cristina; MARTIN DE LA NAVA, Eva Maria; MARTIN ORTEGA FINGER, Maria Dolores; MARTINEZ PEREZ, Jose Antonio; MATEO HERRANZ, Ana Isabel; PEREZ MARTINEZ, Carlos; SANCHEZ MARTINEZ, Concepcion; US2010/160340; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 58530-53-3, 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.58530-53-3, name is 2,4-Dibromopyridine, molecular formula is C5H3Br2N, molecular weight is 236.892, as common compound, the synthetic route is as follows.

General procedure: 2,5-dibromopyridine (119 mg, 0.50 mmol), phenylacetylene (61 mg, 0.6 mmol), i-Pr2NH (101 mg, 1.0 mmol), Pd(OAc)2 (11 mg, 5 mol%), PPh3 (26 mg, 10 mol%), and CuI (9.5 mg, 5 mol%) were dissolved in CH3CN/CH3OH (2:1, 6 mL). The solution was stirred at reflux under nitrogen atmosphere for 24 h and then cooled and the solid was filtered off. The filtrate was then concentrated and the resulting crude product was dissolved in CH2Cl2 (10mL). The solution was washed with brine (10mL), and dried over sodium sulfate. Upon removal of the solvent with a rotavapor, the resulting residue was subjected to column chromatography (petroleum ether/AcOEt, 200:1) to give the desired product 3i (117 mg, 91%) as a white solid.

Statistics shows that 58530-53-3 is playing an increasingly important role. we look forward to future research findings about 2,4-Dibromopyridine.

Reference:
Article; Zhang, Bin; Chen, Rener; Jiang, Huajiang; Zhou, Qizhong; Qiu, Fangli; Han, Deman; Li, Rongrong; Tang, Wenyuan; Zhong, Aiguo; Zhang, Jie; Yu, Xiaochun; Tetrahedron; vol. 72; 22; (2016); p. 2813 – 2817;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products 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

Application of 80194-68-9, 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 80194-68-9, name is 3-Chloro-5-(trifluoromethyl)picolinic acid. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: General procedure for preparing intermediates 3. As shown in scheme 1, to a solution of 3-chloro-5-(trifluoromethyl)picolinicacid 1 (0.5 g, 2.22 mmol) in 5 mL ofacetonitrile, pyridine (0.7 g, 8.87 mmol) and methanesulphonyl chloride (0.51 g,4.43 mmol) was slowly added at -5 0C, and was left to stir at -5 0Cfor 10 min. The corresponding substituted 2-amino-benzoic acid (2.22 mmol) wasadded and left to stir for further 10 min. Pyridine (0.7 g, 8.87 mmol) and methanesulphonylchloride (0.51 g, 4.43 mmol) were slowly added again below 0 0C. Theresulting mixture was stirred at room temperature for 10 h and monitored byTLC. After the completion of reaction above, water (5 mL) was added to themixture to afford a crystalline solid (intermediate 3) via filter and recrystallization from ethanol.

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 80194-68-9, 3-Chloro-5-(trifluoromethyl)picolinic acid.

Reference:
Article; Luo, Dexia; Guo, Shengxin; He, Feng; Wang, Heying; Xu, Fangzhou; Dai, Ali; Zhang, Renfeng; Wu, Jian; Bioorganic and Medicinal Chemistry Letters; vol. 30; 3; (2020);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 53937-02-3, 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. 53937-02-3, name is 4-Benzyloxy-2-(1H)-pyridone. A new synthetic method of this compound is introduced below.

tert-Butyl 2-bromo-9-methyl-5,7,8,9-tetrahydro-6H-pyrido[3′,4′:4,5]pyrrolo[2,3-b]pyridine-6-carboxylate (0.73 g, 2.0 mmol), 4-benzyloxy pyridinone (0.44 g, 2.2 mmol), and Cs2CO3 (0.72 g, 2.2 mmol) were suspended in DMSO (12 mL), and the air was removed under vacuum for 15 min. The system was flushed with Ar, and 8-hydroxyquinoline (87 mg, 0.60 mmol) and copper iodide (0.49 g, 2.6 mmol) were added to the suspension. The evacuation/Ar flushing process was repeated twice more, and the reaction mixture was heated at 130 C. for 18 h under N2. The mixture was cooled, diluted with 5.0:3.5:1.5 NH4Cl(aq.)/NH4OH/H2O (70 mL), and the resulting suspension was stirred at ambient temperature for 30 min. The resulting solids were collected by filtration, dissolved in CH2Cl2 (30 mL) and washed with 5.0:3.5:1.5 NH4Cl(aq.)/NH4OH/H2O (2*30 mL). The resulting organic solution was dried over Na2SO4, filtered, and concentrated to dryness under reduced pressure. Flash chromatography (40 g ISCO column, (1:1 hexanes/EtOAc)/(80:18:2 CH2Cl2/MeOH/NH4OH), 100:0 for 2 column volumes, increased to 50:50 over 12 column volumes and held for 5 column volumes; increased to 0:100 over 10 column volumes and held for 5 column volumes) gave the title compound (0.51 g, 52%) as a yellow foam: 1H NMR (500 MHz, DMSO-d6) delta 8.00 (d, J=8.0 Hz, 1H), 7.80 (d, J=8.0 Hz, 1H), 7.50-7.36 (m, 5H), 7.29 (d, J=8.0 Hz, 1H), 6.15 (dd, J=8.0, 2.5 Hz, 1H), 5.98 (d, J=2.5 Hz, 1H), 5.16 (s, 2H), 4.57 (s, 2H), 3.75 (t, J=5.5 Hz, 2H) 3.67 (s, 3H), 2.88 (t, J=5.5 Hz, 2H), 1.42 (s, 9H); ESI MS m/z 487 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,53937-02-3, 4-Benzyloxy-2-(1H)-pyridone, and friends who are interested can also refer to it.

Reference:
Patent; ALBANY MOLECULAR RESEARCH, INC.; US2012/157460; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem