Category: pyridine-derivatives

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. 1628-89-3, name is 2-Methoxypyridine. A new synthetic method of this compound is introduced below., category: pyridine-derivatives

A 5-liter three-necked round bottom flask was equipped with an overhead mechanical stirrer under nitrogen, the flask was charged with THF (1 L) and cooled to -78 C. To this stirred solution was added tert-butyllithium (1.7 M solution in pentane) (800 mL, 1.36 mol) via canula followed by 2-methoxypyridine (132.2 g, 1.21 mol) at -78 C. The mixture was stirred for 1 h at -78 C. To the mixture was added N-formyl-N, N’, N’-trimethylethylenediamine (176 mL, 1.37 mol) dropwise at -78 C. The reaction mixture was stirred for ca. 30 min at -78 C. before warming to -23 C. over ca. 30 min. To the mixture at -23 C. was added ethylene glycol dimethyl ether (1 L) followed by n-butyllithium (2.5 M solution in hexane) (800 mL, 2.0 mol). The resulting mixture was stirred for ca. 2 h during which time the reaction mixture turned deep green. A 12-L 4-necked round flask was charged with iodine (571 g, 2.25 mol) and ethylene glycol dimethyl ether (2 L) and the resultant solution was cooled to -78 C. The contents of the 5-L flask were transferred via canula to the mixture of iodine and ethylene glycol dimethyl ether in the 12-L flask at -78 C. After the addition was complete, the reaction mixture was stirred for an additional 1 h at -78 C. The cooling bath was removed and the mixture was allowed to warm to about 0 C. and treated with 2 L of water and 2 L of 1 N hydrochloric acid. Methyl t-butyl ether (2L) was added and the layers were separated. The aqueous layer was extracted with 2×1 L of methyl t-butyl ether. The combined organic layers were washed with saturated Na2S2O3 (1.2 L), brine (1.2 L), dried over Na2SO4. After concentration in vacuo, the thick slurry was diluted with hexane (1 L). The mixture was cooled with an ice/water bath for ca. 30 min. The precipitate was filtered and dried in vacuum to yield the title compound as a light yellow solid. 1H NMR (300 MHz, CDCl3) delta 10.22 (s, 1H), 7.86 (1H, d, J=5.3 Hz), 7.54 (1H, d, J=5.3 Hz), 4.06 (3H, s). LCMS (M+H)+ m/z 364 (t=2.26 min.).

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, 1628-89-3, 2-Methoxypyridine.

Reference:
Patent; Wittman, Mark D.; Balasubramanian, Neelakantan; Velaparthi, Upender; Zimmermann, Kurt; Saulnier, Mark G.; Liu, Peiying; Sang, Xiaopeng; Frennesson, David B.; Stoffan, Karen M.; Tarrant, James G.; Marinier, Anne; Roy, Stephan; US2004/44203; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 63897-12-1, 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 63897-12-1, name is 2,4-Dichloro-6-methyl-3-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 2-aminopyrazine (0.900 g, 9.47 mmol) in DMSO (40 mL) was added potassium tert-butoxide (2.13 g, 18.9 mmol) followed by 2,4-dichloro-6-methyl-3-nitropyridine (2.00 g, 9.47 mmol). After stirring for 30 min at rt, sat. NH4Cl solution was added. The organic layer was separated and the water layer was extracted with CH2Cl2 three times. The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated. Chromatography on silica gel (0-70% ethyl acetatehexanes) provided the desired product (567 mg, 23%). MS (ESI) mass calcd. C10H8ClN5O2, 265.04. m/z found, 266.0 [M+H]+. 1H NMR (500 MHz, CDCl3) delta 8.69-8.62 (br s, 1H), 8.38-8.34 (m, 2H), 8.34-8.29 (m, 2H), 2.59-2.56 (m, 3H).

According to the analysis of related databases, 63897-12-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Janssen Pharmaceutica NV; Alcazar Vaca, Manuel Jesus; Andres Gil, Jose Ignacio; Chrovian, Christa C.; Coate, Heather R.; De Angelis, Meri; Dvorak, Curt A.; Gelin, Christine F.; Letavic, Michael A.; Savall, Brad M.; Soyode-Johnson, Akinola; Stenne, Brice M.; Swanson, Devin M.; US2014/275015; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 104830-06-0, 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 104830-06-0, name is 2-Amino-3-iodopyridine. This compound has unique chemical properties. The synthetic route is as follows.

Manufacturing Example 1-2-2 3-Trimethylsilanylethynyl-pyridin-2-ylamine; To a mixture of 3-iodopyridin-2-ylamine (40.2 g, 183 mmol) described in Manufacturing Example 1-2-1, trimethylsilylacetylene (51.7 mL, 366 mmol), copper (I) iodide (3.49 g, 18.3 mmol), N,N-diisopropylethylamine (63.7mL, 366mmol) and N-methylpyrrolidinone (200 mL) was added tetrakis(triphenylphosphine)palladium (0) (10.6 g, 9.15 mmol) under nitrogen atmosphere, which was stirred for 3 hours and 10 minutes at room temperature. Water was added to the reaction solution, which was then extracted with ethyl acetate 4 times. The solvent was concentrated under a reduced pressure. The residue was purified by NH silica gel chromatography (heptane:ethyl acetate=4:1). The resulting solution was concentrated under a reduced pressure, and the residue was purified by silica gel chromatography (heptane:ethyl acetate=2:1 then 1:1) to obtain the title compound (28.1 g, 80.7%).1H-NMR Spectrum (DMSO-d6) delta (ppm): 0.25 (9H, s), 6.09 (2H, brs), 6.51-6.57 (1H, m), 7.50-7.55 (1H, m), 7.95-7.99 (1H, m).

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 104830-06-0, 2-Amino-3-iodopyridine.

Reference:
Patent; Tanaka, Keigo; Yamamoto, Eiichi; Watanabe, Naoaki; US2009/82403; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 98198-48-2, Adding some certain compound to certain chemical reactions, such as: 98198-48-2, name is 2-Amino-5-bromo-4-methylpyridine,molecular formula is C6H7BrN2, 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 98198-48-2.

General procedure: Under inert atmosphere, a mixture of halide F, D, K or P (1.0 equiv.), boronic acid derivative R1-M G or J (1.5 equiv.), PdCI2(dppf)2 (0.1 equiv.) and aqueous Na2CO3 (1.2 M – 3.0 equiv.) in DMF (C=0.1 molL-1) was submitted to microwave irradiation (150C, 15 min, P< 70W). The reaction mixture was hydrolysed, and then extracted with EtOAc twice. The organic layers were combined, washed with brine, dried over MgSO4, concentrated and purified to afford the product. To a solution or suspension of the free base in MeOH, HCl in MeOH (1.25N, 5 equiv.) was added. The mixture was vigorously stirred, then concentrated. The residue was taken in Et2O. The resulting solid was collected, washed with Et2O and dried at 50C under reduced pressure with P2O5. According to the analysis of related databases, 98198-48-2, the application of this compound in the production field has become more and more popular. Reference:
Patent; DOMAIN THERAPEUTICS; MAYER, Stanislas; SCHANN, Stephan; WO2013/174822; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 2402-78-0, name is 2,6-Dichloropyridine. This compound has unique chemical properties. The synthetic route is as follows. category: pyridine-derivatives

According to Table 1, the corresponding 2,6-dichloropyridine, alkyl alcohol,Sodium hydroxide is added to a 250ml or 500ml three-necked flask equipped with a reflux condenser, a stirrer, and a thermometer, and heated to boiling with stirring to maintain reflux.The reaction was sampled for 1 hour and the reaction product was found to be 6-chloro-2-alkoxypyridine, abbreviated as pyridine ether.

With the rapid development of chemical substances, we look forward to future research findings about 2402-78-0.

Reference:
Patent; Shandong Kunda Biological Technology Co., Ltd.; Zhao Zengguo; Wang Jiangtao; Song Cailing; Chen Jialiang; Chen Kaiqing; (7 pag.)CN107954928; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 581-45-3, 4-(Piperidin-4-yl)pyridine, 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, 581-45-3, blongs to pyridine-derivatives compound. Recommanded Product: 4-(Piperidin-4-yl)pyridine

A mixture of 29 (0.252 g; 0.555 mmol), 4- (4-piperidinyl) pyridine (0.090 g, 0.555 mmol), [K2CO3] (0.092 g; 0.66 mmol) in acetonitrile (2 ml) was heated at [85C] under argon atmosphere for 2 hours. The crude mixture was evaporated and purified by flash chromatography eluting with a gradient 5-7% of 3.5 N [NH3] in [MEOH/METHYLENE] chloride to give after trituration in ether/pentane Example 20 as a solid. Yield: 34% [‘H NMR (CDC13)] : 1.2-1. 45 (m, 4H); 1.65 (s, 6H); 1.5-1. 8 (m, 4H); 1.8-1. 95 (m, 4H); 2.18 (t, 2H); 2.38 (s, 6H); 2.5-2. 6 (m, 1H) ; 2.7-2. 8 (m, 2H); 2.95-3. 05 (m, 2H); 3.15-3. 25 (m, 2H); 4- 4.2 (m, br, 1H) ; 4.65-4. 85 (m, br, 1H) ; 6.78 (s, 1H); 6.98 (s, 1H); 7.10 (s, 2H); 7.18 (d, 2H); 8.22 (s, 1H); 8.53 (d, 2H). MS-ESI: 581 [M+H] [+]

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,581-45-3, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2004/18480; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route 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.

General procedure: The coupling reaction was performed as follows: in a typical process, 5-methyl-2-(1H)-pyridone(1 mmol), aryl halide (1 mmol), base (2 mmol) and solvent (5 mL) were added to an oven-dried tube containing 5% (based on copper) MOF catalyst or copper salt. The mixture was stirred at desired temperature for 2 h. After being cooled to room temperature, the catalyst was filtrated and washed with ethyl acetate. The products were isolated by a series 1500 preparative high performance liquid chromatography system (SSI, Charlotte, NC, USA) equipped with a UV-VIS detector, using a Kromasil C18 column (50 x 250 mm) and gradient elution with a H2O (A)-acetonitrile (B) the mobile phase. The gradient program was 0 min, 10% B; 20 min, 35% B. The flow rate of mobile phase was 40 mL/min, and the detection wavelength was 220 nm. Fractions were collected and evaporated to afford the pure products.

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 1003-68-5, 5-Methylpyridin-2(1H)-one.

Reference:
Article; Long, Wei; Qiu, Wenge; Guo, Chongwei; Li, Chuanqiang; Song, Liyun; Bai, Guangmei; Zhang, Guizhen; He, Hong; Kuznetsov, Maxim L.; Molecules; vol. 20; 12; (2015); p. 21178 – 21192;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 67625-37-0, 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.67625-37-0, name is Ethyl 6-bromoimidazo[1,2-a]pyridine-2-carboxylate, molecular formula is C10H9BrN2O2, molecular weight is 269.0947, as common compound, the synthetic route is as follows.

A stirred solution of ethyl 6-bromoimidazo[l,2-a]pyridine-2-carboxylate(1-6, 4.0 g, 14.86 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(l,3,2-dioxaborolane) (A17, 6.42 g, 25.27 mmol) and KOAc(2.47 gm, 25.27 mmol) in dioxane(100 mL) was degassed with argon for 30 minutes. Then[I,G- Bis(diphenylphosphino)ferrocene]palladium(II) dichloride(0.761 g, 1.04 mmol) was added. The reaction mixture was heated at 90C for 16 h. After completion, reaction mixture quenched with water and extracted with ethyl acetate. The organic layer was separated, dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtain the crude. This crude washed with 30% diethyl ether in hexane and concentrated the filtrate to offered ethyl 6-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)imidazo[l,2-a]pyridine-2-carboxylate 1-27 as brown gummy liquid. Yield: 7.8 g LC-MS(ES) m/z = 235.09[M+H]+.

The chemical industry reduces the impact on the environment during synthesis 67625-37-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; JUBILANT BIOSYS LIMITED; VADIVELU, Saravanan; RAJAGOPAL, Sridharan; BURRI, Raghunadha Reddy; GARAPATY, Shivani; SIVANANDHAN, Dhanalakshmi; THAKUR, Manish Kumar; NATARAJAN, Tamizharasan; SWAMY, Indu N; NAGARAJU, Nagendra; KANAGARAJ, Subramaniam; MOHD, Zainuddin; SARKAR, Sayantani; SAMANTA, Swapan Kumar; ., Hariprakash; (284 pag.)WO2019/102494; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 624-28-2 ,Some common heterocyclic compound, 624-28-2, molecular formula is C5H3Br2N, 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.

General procedure: Procedure (take intermediate 3a as an example): 2,5-dibromopyridine (61.5 mmol), phenol (64.6 mmol), cuprous iodide (6.15 mmol), and Cs2CO3 (92 mmol) were placed in a 250 mL dried flask. Add 150 mL DMSO, then add TMEDA (6.15 mmol), heated to 110 degrees under Ar protection (Unless otherwise specified, the temperature in the present invention is in degrees Celsius C), react for about 20 hours, TLC conversion complete. After cooling to room temperature, a large amount of ethyl acetate was added, the mixture was washed 4 times with water and extracted twice with ethyl acetate. The combined EA (ethyl acetate) phase was washed with brine, and the organic layer was dried, filtered and evaporated to dryness to give the product as a brown oil.

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. 624-28-2, 2,5-Dibromopyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hangzhou He Zheng Pharmaceutical Co., Ltd.; Zhou Xinglu; Liu Xingguo; Luo Wenhua; Zhong Shichun; Huang Jinglai; Dong Xiaowu; Huang Wenhai; Hu Miao; (55 pag.)CN108069974; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 15471-17-7, 3-(Pyridin-1-ium-1-yl)propane-1-sulfonate, 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, 15471-17-7, blongs to pyridine-derivatives compound. HPLC of Formula: C8H11NO3S

General procedure: Toa mixture of toluene (30 mL) and 1,3-propane sulfone (0.10 mol, 12.2 g) in a 100 mLround bottomed flask was added pyridine (0.11 mol, 8.7 g, 8.9 mL). The reactionmixture was stirred for 24 h at 50 oC under a nitrogen atmosphereuntil a white precipitate (PyPS) was formed. After filtration, washing withdiethyl ether and drying in a vacuum, PyPS was obtained. To an aqueous solutionof H3PW12O40 (0.03 mol, 86.4 g) was added PyPS(0.09 mol, 18.1 g) and then the mixture was stirred at room temperature for 24h. Finally, the solution was removed in vacuum to give the product [PyPS]3PW12O40as a solid. Thus [MIMPS]3PW12O40, [MIMPS]3PMo12O40,[PyPS]3PMo12O40, [TEAPS]3PW12O40and [TEAPS]3PMo12O40 were prepared usingaccording starting materials.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,15471-17-7, its application will become more common.

Reference:
Article; Fu, Renzhong; Yang, Yang; Ma, Yunsheng; Yang, Fei; Li, Jingjing; Chai, Wen; Wang, Quan; Yuan, Rongxin; Tetrahedron Letters; vol. 56; 30; (2015); p. 4527 – 4531;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem