Pyridine-derivatives

Application of 16063-69-7 , The common heterocyclic compound, 16063-69-7, name is 2,4,6-Trichloropyridine, molecular formula is C5H2Cl3N, 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.

Samples of 0.500 g (2.74 mmol) 2,4,6-trichloropyridine, 0.487 g (3.29 mmol) trans-2-phenylvinylboronic acid, 0.057 g (0.082 mmol) Pd(Cl2)(PPh3)2, and 1.17 g (5.48 mmol) K3PO4 were combined in 20 mL THF. To this heterogeneous mixture, 2.5 mL of H2O were added. The resulting solution was heated at reflux for 20 h. After being cooled to room temperature, the resulting residue was extracted from water with three times with ether. The combined organic layers were washed with brine, dried over anhydrous MgSO4, and the solvent removed with a rotary evaporator. The product was purified by column chromatography (5-10% EtOAc in hexanes) to provide pure 14 (0.323 g, 47% yield). 1H NMR (500 MHz, CDCl3) delta 7.01 (d, J=16.08 Hz, 1H), 7.19 (s, 1H), 7.25 (s, 1H), 7.34 (t, J=7.07 Hz, 1H), 7.40 (t, J=7.50 Hz, 2H), 7.57 (d, J=7.29 Hz, 2H), 7.70 (d, J=15.87 Hz, 1H). 13C NMR (500 MHz, CDCl3) delta 120.6, 121.9, 125.1, 127.4, 128.8, 129.0, 135.6, 135.7, 145.8, 151.7, 157.1. HRMS (ESI+) m/z calcd for C13H10NCl2+ 250.0190. found 250.0188. mp 36-38 C. (recryst. from EtOAc/hexanes).

The synthetic route of 16063-69-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE BOARD OF TRUSTEES OF THE UNIVERSITY OF ILLINOIS; DUKE UNIVERSITY; Katzenelienbogen, John; McDonneli, Donald; Norris, John D,; Parent, Alexander; Pollock, Julie; Gunther, Jillian; Carlson, Kathryn E.; Martin, Teresa; (196 pag.)US2016/229811; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 117007-52-0, 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. 117007-52-0, name is 3-Iodo-1H-pyrazolo[3,4-b]pyridine. A new synthetic method of this compound is introduced below.

Step 3: tert-butyl 3-iodo-1H-pyrazolo[3,4-b]pyridine-1-carboxylate (49-4); A magnetically stirred suspension of 1.20 g (4.90 mmol) of 3-iodo-1H-pyrazolo[3,4-b]pyridine (49-3) in 35 mL of anhydrous acetonitrile under a nitrogen atmosphere was treated with 720 muL (5.15 mmol) of triethylamine, followed by 599 mg (4.90 mmol) of 4-dimethylaminopyridine. The resulting solution was treated approximately 2 minutes later with a solution of 1.29 g (5.88 mmol) of BOC anhydride in 5 mL of anhydrous acetonitrile, and the resulting solution stirred at room temperature for 72 hours. The crude reaction mixture was partitioned between ethyl acetate and water, and the organic layer was separated, washed with brine, and dried in vacuo (anhydrous MgSO4). The dried extract was filtered, and the filtrate concentrated in vacuo to give 2 g of the crude solid product. The product was purified by flash chromatography over silica gel with 20:1 hexanes/EtoAc (crude material dissolved in chloroform, impregnated on silica, and the silica applied to the top of the column) to give the desired product as a white solid. M+=245 (M-100, loss of BOC). 1H NMR (CDCl3): 1.73(s, 9H), 7.36(dq, 1H), 7.84(dd,1H), 7.78(dd,1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,117007-52-0, 3-Iodo-1H-pyrazolo[3,4-b]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; Saggar, Sandeep A.; Sisko, John T.; Tucker, Thomas J.; Tynebor, Robert M.; Su, Dai-Shi; Anthony, Neville J.; US2007/21442; (2007); 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. 677728-92-6, name is 2-Fluoropyridine-5-carbaldehyde. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C6H4FNO

A mixture of [3-(6-morpholin-4-yl-9-piperidin-4-yl-9H-purin-2-yl)phenyl]methanol (30 mg, 0.076 mmol), NaCNBH3 (25 mg, 0.40 mmol), zinc chloride (20 mg, 0.183 mmol) and 6-fluoronicotinicaldehyde (14 mg, 0.11 mmol) in methanol is stirred for 24 hours at room temperature. The mixture is then filtered, dissolved in DMSO (1 mL) and purified by chromatography by HPLC to give 9 mg (24% yield) of the title product.

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, 677728-92-6, 2-Fluoropyridine-5-carbaldehyde.

Reference:
Patent; Wyeth; US2008/233127; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 19337-97-4, 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.19337-97-4, name is trans-3-(3-Pyridyl)acrylic acid, molecular formula is C8H7NO2, molecular weight is 149.15, as common compound, the synthetic route is as follows.

Synthesis of 3-(3-pyridinyl)propanoic acid beta-(3-Pyridyl)-acrylic acid (10 g) is placed in a Parr hydrogenation bottle with 150 ml of glacial acetic acid, 100 ml of absolute ethanol and a large scoop of palladium on carbon catalyst. The solution is shaken at 50 psi of hydrogen and re-pressurized as needed until hydrogen uptake ceases (approximately 3 hours). The solution is filtered through celite, washed with ethanol and the solvent is evaporated in vacuo and azeotroped with toluene to yield the desired product as white crystals.

Statistics shows that 19337-97-4 is playing an increasingly important role. we look forward to future research findings about trans-3-(3-Pyridyl)acrylic acid.

Reference:
Patent; Procter & Gamble Pharmaceuticals, Inc.; US5391743; (1995); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 124433-70-1, Adding some certain compound to certain chemical reactions, such as: 124433-70-1, name is 6-Fluoropyridine-2-sulfonamide,molecular formula is C5H5FN2O2S, 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 124433-70-1.

To 6-phenyl-2-(2,4,6-trimethylphenoxy)pyridine-3-carboxylic acid (150 mg, 0.450 mmol), HATU (171 mg, 0.450 mmol), DMF (1.5 mL), and triethylamine (137 mg, 188 muL, 1.35 mmol) was added 6-fluoropyridine-2-sulfonamide (79.3 mg, 0.450 mmol) was added and the reaction mixture was allowed to stir at 65 C. for 1 h. The reaction mixture was filtered and purified via HPLC (1%-99%) ACN:H2O with a 0.1% HCl modifier to give N-[(6-fluoro-2-pyridyl)sulfonyl]-6-phenyl-2-(2,4,6-trimethylphenoxy)pyridine-3-carboxamide (Compound 698) (79 mg, 36%) 1H NMR (400 MHz, DMSO-d6) delta 8.37 (q, J=7.8 Hz, 1H), 8.16 (dd, J=7.5, 2.1 Hz, 1H), 8.12 (d, J=7.8 Hz, 1H), 7.80-7.73 (m, 3H), 7.59 (dd, J=8.3, 2.2 Hz, 1H), 7.41 (ddt, J=5.5, 3.8, 2.2 Hz, 3H), 6.94 (s, 2H), 2.28 (s, 3H), 2.01 (s, 6H). ESI-MS m/z calc. 491.1315. found 492.4 (M+1)+. Retention time: 2.19 minutes.

According to the analysis of related databases, 124433-70-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; Miller, Mark Thomas; Anderson, Corey; Arumugam, Vijayalaksmi; Bear, Brian Richard; Binch, Hayley Marie; Clemens, Jeremy J.; Cleveland, Thomas; Conroy, Erica; Coon, Timothy Richard; Frieman, Bryan A.; Grootenhuis, Peter Diederik Jan; Gross, Raymond Stanley; Hadida-Ruah, Sara Sabina; Haripada, Khatuya; Joshi, Pramod Virupax; Krenitsky, Paul John; Lin, Chun-Chieh; Marelius, Gulin Erdgogan; Melillo, Vito; McCartney, Jason; Nicholls, Georgia McGaughey; Pierre, Fabrice Jean Denis; Silina, Alina; Termin, Andreas P.; Uy, Johnny; Zhou, Jinglan; (590 pag.)US2016/95858; (2016); 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. 6959-47-3, name is 2-(Chloromethyl)pyridine hydrochloride. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 6959-47-3

Synthesis of [N,N?-Dimethyl-N,N?-bis-(pyridine-2-ylmethyl)-1,2-diaminoethane] was taken from a previously reported procedure [16]. 2-(chloromethyl)pyridine hydrochloride (1.501 g, 9.15 mmol) dissolved in 5 mL deionized (DI) water was added dropwise to an aqueous solution containing K2CO3 (2.556 g, 18.49 mmol) dissolved in 7.5 mL DI water. The resulting mixture was stirred for 30 min. The mixture was extracted with CH2Cl2 (3×10 mL). The organic phase was collected and dried with anhydrous Na2SO4. The dried solution was concentrated in vacuo to afford orange oil. A solution containing N,N?-dimethylethylenediamine (0.471 mL, 4.38 mmol) in 15 mL CH2Cl2 was added dropwise to the aforementioned orange oil dissolved in 5 mL CH2Cl2. An aqueous solution containing NaOH (0.311 g, 7.78 mmol) dissolved in 7.6 mL DI water was slowly added to organic mixture and stirred at room temperature. After 60 h, a second portion of NaOH solution(0.318 g, 7.95 mmol) was quickly added to the mixture. The combined mixture was extracted with CH2Cl2 (3×20 mL) and dried with anhydrous Na2SO4. The organic solution was concentrated in vacuo to afford a brown oil, BPMEN (Yield: 0.631 g, 2.33 mmol, 70%) 1H NMR(500 MHz, CD2Cl2) delta 8.46 (dt, 2H, pyridine ring), 7.80 (m, 2H, pyridinering), 7.51 (m, 2H, pyridine ring), 7.30 (m, 2H, pyridine ring), 3.70 (m,4H, -CH2), 2.66 (m, 4H, -CH2), 2.27 (s, 6H, -CH3). ESI-MS (MeOH).Observed m/z 271.25 [BPMEN+H+] (z=1); simulated m/z 271.19.

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, 6959-47-3, 2-(Chloromethyl)pyridine hydrochloride.

Reference:
Article; Pella, Bruce J.; Niklas, Jens; Poluektov, Oleg G.; Mukherjee, Anusree; Inorganica Chimica Acta; vol. 483; (2018); p. 71 – 78;,
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.126325-47-1, name is 6-Bromo-2-methylpyridin-3-amine, molecular formula is C6H7BrN2, molecular weight is 187.04, as common compound, the synthetic route is as follows.Quality Control of 6-Bromo-2-methylpyridin-3-amine

Into a 50-mL seal tube was placed methyl 6-bromo-2-methylpyridin-3 -amine (500 mg, 2.67 mmol) in MeOH (15 mL) and Pd(OAc)2(120 mg, 0.53 mmol), dppf (444 mg, 0.80 mmol), TEA (809 mg, 8.01 mmol). The seal tube was evacuated and flushed three times with CO. The resulting solution was stirred for 5 h at 100C under 10 atm of CO. Then the solution was concentrated under vacuum. The residue was eluted from a silica gel column with ethyl acetate/petroleum ether (1 : 1).This resulted in 351 mg (79.2 %) of the title compound as a light yellow solid. MS-ESI: 167 (M+l).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,126325-47-1, 6-Bromo-2-methylpyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; IFM TRE, INC.; GLICK, Gary; ROUSH, William R.; VENKATRAMAN, Shankar; SHEN, Dong-Ming; GHOSH, Shomir; KATZ, Jason; SEIDEL, Hans Martin; FRANCHI, Luigi; WINKLER, David Guenther; OPIPARI JR., Anthony William; (783 pag.)WO2019/23147; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 18653-75-3, 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 18653-75-3, name is 2-(1H-Imidazol-2-yl)pyridine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a mixture of 1.45 g (10 mmol) of 2-pyridyl-1H-imidazole, 0.62 g (11 mmol) of powdered KOH, and 10 mL of ethylene glycol dimethyl ether was added dropwise 0.68 g (11 mmol) of methyl iodide with vigorous stirring at 3-5 C, maintaining the reaction temperature no higher than 8 C. The mixture was stirred at this temperature for 0.5 h, and then poured into 100 mL of water. The reaction product was filtered off or extracted with chloroform (2×50 mL). The extract was dried over calcium chloride, chloroform was distilled off. The residue was extracted with hot hexane (3×50 mL) and evaporated to give the corresponding 1-methyl-2-pyridyl-1H-imidazole.

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 18653-75-3, 2-(1H-Imidazol-2-yl)pyridine.

Reference:
Article; El?chaninov; Aleksandrov; Klushin; Russian Journal of General Chemistry; vol. 86; 7; (2016); p. 1581 – 1583; Zh. Obshch. Khim.; vol. 86; 7; (2016); p. 1102 – 1105,3;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 2002-04-2, 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.2002-04-2, name is 5-(Pyridin-4-yl)-1,3,4-thiadiazol-2-amine, molecular formula is C7H6N4S, molecular weight is 178.21, as common compound, the synthetic route is as follows.

General procedure: An equimolar amount of 5-(pyridin-4-yl)-1,3,4-thiadiazol-2-amine (3c) dissolve in 10-15mL of tetrahydrofuran (THF), add 2-3 drops of triethylamine, to this solution add 1.5mol different aryl chlorides gradually, continuous stirring for 3h on ice bath(0C). After completion of reaction solid will precipitate out, washed with sodium bicarbonate solution to remove excess of chloride and recrystallized from ethanol to get pure compound.

The chemical industry reduces the impact on the environment during synthesis 2002-04-2, I believe this compound will play a more active role in future production and life.

Reference:
Article; Patel, Harun; Jadhav, Harsha; Ansari, Iqrar; Pawara, Rahul; Surana, Sanjay; European Journal of Medicinal Chemistry; vol. 167; (2019); p. 1 – 9;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 16867-03-1, name is 2-Amino-3-hydroxypyridine. A new synthetic method of this compound is introduced below., category: pyridine-derivatives

15.6 g (141.6 mmol) of 2-amino-3-hydroxypyridine are initially charged in 300 ml of glacial acetic acid, 15.6 g (141.6 mmol) of 2-amino-3-hydroxypyridine are initially charged in 300 ml of glacial acetic acid, [0294] 5.1 g of 5% rhodium/ carbon catalyst are added and the mixture is hydrogenated in a 600 ml vessel (material: Hastelloy) at room temperature (20 C.) at 4.5 bar for about 16 hours. The entire reaction mixture is then filtered (removal of the catalyst) and concentrated under reduced pressure, and the residue that remains is recrystallized from an ethanol/ether mixture. This gives 5.9 g (23.9% of theory) of a (2:1) mixture of 2-amino-3-hydroxypyridine and 2-amino-3,4,5,6-tetrahydropyridin-2-ol acetate CH NMR spectrum: some Py-H) which can be used for the next reaction. [0295] 1H NMR (600 MHz, D2O) delta 1.79 (br., m, 1H), 1.90-1.92 (m, 1H), 1.99-2.00 (br., m, 1H), 2.22 (br., m, 1H), 3.37 (m, 2H), 4.52 (m, 1H), 6.77-6.78 (m, 1H), 7.18-7.19 (m, 1H), 7.28-7.29 (m, 1H) ppm; At room temperature, 1.0 g (5.74 mmol) of the (2:1) mixture of 2-amino-3-hydroxypyridine and 2-amino-3,4,5,6-tetrahydropyridin-2-ol acetate (cf. step 1) are stirred with 1.26 g (7.79 mmol) of 1,1?-carbonyldiimidazole (CDI), 39.9 mg of 4-dimethylaminipyridine (DMAP) in 6 ml of dichloromethane, and 1.2 ml of triethylamine are added. The entire reaction mixture is then stirred at room temperature for another about 24 hours. The reaction mixture is then concentrated under reduced pressure, the residue that remains is taken up in ethyl acetate and the organic phase is washed with water. The organic phase is separated off and then dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue that remains is purified chromatographically by medium-pressure chromatography (cyclohexane/acetone gradient). This gives 753.0 mg (93.2% of theory) of a mixture of oxazolo[4,5-b]-5,6,7,7a-tetrahydropyridin-2(4H)-one [0301] and oxazolo[4,5-b]pyridin-2(3H)-one (cf. WO 2010/135014 A1) (1H NMR spectrum: some Py-H and LC-MS m/z: 137.0) which can be used for the next reaction. [0302] LC-MS (ESI positive): m/z found: 141.0 [M++H]. [0303] C6H8N2O2 calculated: 140.0.

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, 16867-03-1, 2-Amino-3-hydroxypyridine.

Reference:
Patent; Jeschke, Peter; Schindler, Michael; Woelfel, Katharina; Ebbinghaus-Kintscher, Ulrich; Voerste, Arnd; Malsam, Olga; Losel, Peter; Goergens, Ulrich; US2014/113824; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem