Pyridine-derivatives

Related Products of 872355-64-1 , The common heterocyclic compound, 872355-64-1, name is 1H-Pyrrolo[3,2-b]pyridine-5-carboxylic acid, molecular formula is C8H6N2O2, 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.

Preparation of compound 9a: 3-iodo-lH-pyrrolo[3,2-b]pyridine-5-carboxylic acidTo a solution of lH-pyrrolo[3,2-b]pyridine-5-carboxylic acid (0.400 g, 2.467 mmol, Adesis, New Castle, DE) in DMF (4.9 mL) was added I2 (0.626 g, 2.467 mmol) and KOH (0.346 g, 6.17 mmol). The mixture was stirred at RT for 1 h. The mixture was poured into ice and H20 (30 mL) containing sodium bisulfite (0.257 g, 2.467 mmol). The reaction was acidified with 5 M HCl. A yellow solid precipitated out and was collected by filtration, washed with H20 and dried overnight in a vacuum oven to give 3-iodo-lH- pyrrolo[3,2-b]pyridine-5-carboxylic acid (0.516 g, 1.791 mmol, 72.6 % ). MS (ESI, pos. ion) m/z: 289.0 (M+l). .H NMR (400 MHz, DMSO-d6) delta ppm 7.91 (2 H, s), 8.01 (1 H, d, J=2.74 Hz), 12.03 – 12.11 (1 H, m).

The synthetic route of 872355-64-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; WANG, Hui-Ling; CEE, Victor, C.; HERBERICH, Bradley, J.; JACKSON, Claire, L., M.; LANMAN, Brian, Alan; NIXEY, Thomas; PETTUS, Liping, H.; REED, Anthony, B.; WU, Bin; WURZ, Ryan; TASKER, Andrew; WO2012/129338; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 138402-36-5, 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.138402-36-5, name is 3-(Aminomethyl)-5-chloropyridine, molecular formula is C6H7ClN2, molecular weight is 142.5862, as common compound, the synthetic route is as follows.

To a rnixture of 6-brorno-2,4-dichloroquinazoline (1.946 g, 7 rnrnol) in THF (Volurne: 20 rnl) was added (5-chloropyridin-3-yl)rnethanarnine (0.998 g, 7.0 rnrnol) and then Et3N (1.463 rnl, 10.50 rnrnol) at rt. The rnixture was stirred at 0 00 for 15 rnin and then warrned to RT for 1.5 h (cornplete by TLC). The rnixture was poured into EtOAc/H20 (50 rnL/50 rnL). The aqueous layerwas extracted with EtOAc (50 rnL x 2). The cornbined organic layer was dried (Na2504) and filtered. After rernoval of solvent, the product was and sorne EtOAc (5-10 rnL), sonicated, and then added hexane (200 rnL) slowly. The solid was filtered and triturated with hexane and then dried to give 6-brorno-2-chloro-N-((5-chloropyridin-3-yl)rnethyl)quinazolin-4-arnine (2.31 g, 6.01 rnrnol, 86 % yield) as a solid.

The chemical industry reduces the impact on the environment during synthesis 138402-36-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; STROVEL, Jeffrey William; YOSHIOKA, Makoto; MALONEY, David J.; YANG, Shyh Ming; JADHAV, Ajit; URBAN, Daniel Jason; (334 pag.)WO2017/91661; (2017); A1;,
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Pyridine | C5H5N – PubChem

Synthetic Route of 886373-28-0, 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. 886373-28-0, name is 5-Bromo-3-fluoropicolinonitrile, molecular formula is C6H2BrFN2, 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.

A mixture of 5-bromo-3-fluoro-pyridine-2-carbonitrile (21.0 g, 100 mmol) in concentrated HCI (200 ml)was refluxed at 140C for 4 hours. After cooling to room temperature, the reaction mixture was pouredinto ice-water. The precipitated solid was filtered under vaccum and dried to give the desired compound(18.3 g). 1H NMR (d6-DMSO, 400MHz): 13.76 (s, 1H), 8.64 (s, 1H), 8.33-8.36 (dd, 1H). 19F NMR (d6-DMSO, 300MHz): -113.70 (d, iF).

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 886373-28-0, 5-Bromo-3-fluoropicolinonitrile.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; JUNG, Pierre, Joseph, Marcel; MUEHLEBACH, Michel; EDMUNDS, Andrew; RAWAL, Girish; SIKERVAR, Vikas; PABBA, Jagadish; (144 pag.)WO2017/174449; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 3430-26-0, Adding some certain compound to certain chemical reactions, such as: 3430-26-0, name is 2,5-Dibromo-4-methylpyridine,molecular formula is C6H5Br2N, 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 3430-26-0.

To a solution of 2,5-dibromo-4-methylpyridine (2 g) in acetonitrile (40 ml) at room temperature under argon were added sodium iodide (4.8 g) then acetyl chloride (0.94 g). After 3 hours stirring at room temperature the white solid formed was filtered off and the filtrate was neutralized with aqueous saturated solution of sodium hydrogenocarbonate. The organic phase was dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (ethyl acetate / cyclohexane) to afford the title product as a brown solid (2.04 g). 1H-NMR (CDC13, 400 MHz): 8.40 (s, 1H), 7.60 (s, 1H), 2.30 (s, 3H),

According to the analysis of related databases, 3430-26-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; CASSAYRE, Jerome Yves; RENOLD, Peter; EL QACEMI, Myriem; PITTERNA, Thomas; TOUEG, Julie Clementine; WO2011/67272; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1186637-43-3, 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 1186637-43-3, name is 3-Bromo-6-methoxypicolinonitrile. This compound has unique chemical properties. The synthetic route is as follows.

Steps 3 and 4: preparation of ethyl 2-(2-cyano-6-methox pyridin-3-yl)-3-ethox acrylate (6D): A mixture of 3D (1.0 g, 4.7 mmol), bis(pinacolato)diboron (1.7 g, 7.0 mmol), Pd(dppf)Cl2 (360 mg, 0.5 mmol), and KOAc (1.0 g, 10.0 mmol) in dioxane (50 mL) was degassed and stirred at 80C for 2 h under N2. After the mixture was cooled to r.t. and compound 5D (1.30 g, 4.8 mmol), Pd(PPh3)4 (550 mg, 0.5 mmol), K2C03 (1.4 g, 10.0 mmol), and H20 (10 mL) was added, and the mixture was stirred at 90C for 3 h under N2. The mixture was extracted with EtOAc (200 mL X 2), washed with sat NaCl (100 mL), dried over Na2S04, concentrated and purified by column (PE : EtOAc = 3:1) to give the product as white solid (600 mg, 48%).

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 1186637-43-3, 3-Bromo-6-methoxypicolinonitrile.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC; CHEN, Huifen; CRAWFORD, Terry; MAGNUSON, Steven, R.; NDUBAKU, Chudi; WANG, Lan; WO2013/113669; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 56673-34-8 ,Some common heterocyclic compound, 56673-34-8, molecular formula is C5H4BrNS, 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.

To a solution of 5-bromopyridine-2-thiol (3.9 g) in THE (100 mL) was added NaH (1.24 g) at 0C and the mixture was stirred at 0C for 30 minutes. Then (bromomethyl)cyclopropane (2.79 g) was added. The mixture was allowed to warm to RT and stirred for 6 hours. The mixture was poured into ice water (200 mL) and extracted with EA (100 mL x 3). The combined organic phases were washed with brine(50 mL) and then dried over Na2504. After filtration and evaporation of the solvent, the residue was purified by SGC (eluent: PE) to provide the subtitle compound. MS ESI:m/z = 244 [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,56673-34-8, its application will become more common.

Reference:
Patent; SANOFI; SCHWINK, Lothar; BUNING, Christian; GLOMBIK, Heiner; GOSSEL, Matthias; KADEREIT, Dieter; HALLAND, Nis; LOHMANN, Matthias; POeVERLEIN, Christoph; RITTER, Kurt; WO2015/150565; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1196152-34-7, 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. 1196152-34-7, name is 2-Bromo-6-methoxypyridin-4-amine, molecular formula is C6H7BrN2O, 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.

Example 1 2-[(2-Bromo-6-methoxypyridin-4-ylamino)methyl]phenol Synthesis according to Scheme 1, Method 1a 400 mg (1.97 mmol) of 2-bromo-6-methoxypyridin-4-ylamine (starting materials 1) are added to a mixture of 363 mg (2.96 mmol, 1.5 eq) of 2-hydroxybenzaldehyde (starting materials 2) and 184 mg (2.96 mmol, 1.5 eq) of acetic acid in 10 mL of THF in the presence of molecular sieve. After 5 minutes at ambient temperature, 835 mg (3.94 mmol, 2 eq) of sodium triacetoxyborohydride are added and the mixture is left to stir for 2H at ambient temperature. The reaction medium is diluted with 50 mL of ethyl acetate and then the mixture is washed with 50 mL of a saturated solution of ammonium chloride, followed by three times 50 mL of water. The organic phase is concentrated to dryness and the residue is purified by silica chromatography, elution being carried out with a mixture of heptane/ethyl acetate (7/3). 2-[(2-Bromo-6-methoxypyridin-4-ylamino)methyl]phenol is obtained in the form of a beige solid. Melting point=137 C. NMR 1H (DMSO) 3.69 (s, 3H); 4.17 (d, 2H, J=5.2 Hz); 5.81 (s, 1H); 6.45 (s, 1H) 6.75 (t, 1H, J=7.4 Hz); 6.82 (d, 1H, J=8 Hz); 7.07 (t, 1H, J=7.7 Hz); 7.12 (d, 1H, J=7.4 Hz); 7.17-7.19 (m, 1H); 9.64 (s, 1H).

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 1196152-34-7, 2-Bromo-6-methoxypyridin-4-amine.

Reference:
Patent; GALDERMA RESEARCH & DEVELOPMENT; Poinsard, Cedric; Collette, Pascal; Mauvais, Pascale; Linget, Jean-Michel; Rethore, Sandrine; US2013/178633; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 6515-09-9, 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. 6515-09-9, name is 2,3,6-Trichloropyridine. A new synthetic method of this compound is introduced below.

Step A. (3,6-dichloro-pyridin-2-yl)-acetic acid ethyl ester Malonic acid t-butyl ester ethyl ester (7.1 mL, 36 mmol) was added via syringe over one minute with swirling to a frozen mixture of NaH (968 mg, 38.3 mmol) in DMSO (10 mL) at 0 C. The ice bath was removed and the mixture was stirred at rt for 15 min, and then at 115 C. for less than a minute until H2 evolution had subsided, and was then allowed to cool to rt. A solution of 2,3,6-trichloropyridine (3.26 g, 17.9 mmol) (J. Chem. Soc. C: Organic 1375, 1970) in DMSO (12 mL) was added, and the reaction stirred at 115 C. for 4 h. The reaction was then cooled to rt, shaken with 0.5 M NaH2PO4 (100 mL), and extracted with ether (1*50 mL; 2*25 mL). The organic layers were combined, washed with brine (1*20 mL), dried (Na2SO4), and concentrated under high vac at 95 C. to give a mixture of dichloro-pyridin-2-yl-malonic acid tert-butyl ester ethyl ester regioisomers as a clear amber oil (6.40 g) that was immediately used in the next step without further purification or characterization.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6515-09-9, 2,3,6-Trichloropyridine, and friends who are interested can also refer to it.

Reference:
Patent; Player, Mark R.; Lu, Tianbao; Hu, Huaping; Zhu, Xizhen; Teleha, Christopher; Kreutter, Kevin; US2007/225282; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 15103-48-7 , The common heterocyclic compound, 15103-48-7, name is Pyridine-2-sulfonic acid, molecular formula is C5H5NO3S, 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 dried Schlenck tube was charged with pyridine sulfonicacid (PySO3H,0.342 mmol) and KOtBu (0.342 mmol). Afteraddition of methanol, the reaction mixture was allowed to stirfor 30min then [RuCl2(p-cymene)]2 (0.1 g, 0.163 mmol)wasadded. The reaction mixture was stirred under nitrogen for 24h. The yellow suspension became a clear red solution withina few minutes. As the reaction progress, the solution becamecloudy then an orange-yellow solid appeared. The solid wascentrifuged and washed with diethyl ether (2 x 10 mL).The additional compound was obtained from the supernatantby subsequently drying, then dissolving the residuein dichloromethane followed by precipitation with hexane.Orange yellowsolid; yield: 106 mg (76%); Anal.Calcd. forC15H18ClNO3RuS:C41.96;H4.22;N3.26; S 7.45. Found:C41.86;H4.11;N3.58; S 7.24. FTIR (KBr, cm-1): 3051, 2974,1591, 1288, 1436; 1HNMR(CDCl3, delta): 8.76 (d, 1H, J= 5.1),8.01 (m, 1H), 7.88 (d, 1H, J=7.5), 7.57 (t, 1H), 5.78 (d, 1H, J=5.7), 5.69 (d, 1H, J= 5.7), 5.59 (d, 1H, J 6.0), 5.49 (d, 1H, J=6.0), 3.05 (m, 1H), 2.22 (s, 3H), 1.36 (t, 6H, J=7.2); 13CNMR(CDCl3, delta): 157.34, 153.57, 140.57, 127.84, 122.79, 103.97,97.65, 82.10, 81.92, 81.64, 80.54, 30.96, 22.91, 21.65, 18.39;ESI-MS: 394.0051 (M-Cl)+ calculated for C15H18NO3RuS,found 394.0026.

The synthetic route of 15103-48-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Singh, Keisham S; Sawant, Sneha G; Kaminsky, Werner; Journal of Chemical Sciences; vol. 130; 9; (2018);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 39856-57-0, 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.39856-57-0, name is 2,6-Dibromopyridin-3-amine, molecular formula is C5H4Br2N2, molecular weight is 251.91, as common compound, the synthetic route is as follows.

Example 146 (Method N); N-(5-(3-(4-methoxyphenylsulfonamido)phenyl)thiazolo[5,4-b]pyridin-2-yl)acetamide; Step 1. N-(5-bromothiazolor5,4-blpyridin-2-yl)acetamide; 2,6-dibromopyridin-3-amine (4.235 g, 16.8 mmol) was dissolved in acetone and acetyl isothiocyanate(1.85 ml, 21.0 mmol) was added. The flask was fit with a reflux condensor and placed in a preheated oil bath (65 – 70 C) and stirred under nitrogen for 2.5 hours. Then, the reaction was cooled to room temperature, poured into water, and filtered. The solid was washed with water, saturated sodium bicarbonate, and water again, and then collected and dried under high vacuum to afford N-(5- bromothiazolo[5,4-b]pyridin-2-yl)acetamide (5.54 g, Yield > 100%).MS (ESI pos. ion) m/z: 272 (MH+, 79Br), 274 (MH+, 81Br). Calculated exact mass for C8H6BrN3OS 271 (79Br), 273 (81Br).

Statistics shows that 39856-57-0 is playing an increasingly important role. we look forward to future research findings about 2,6-Dibromopyridin-3-amine.

Reference:
Patent; AMGEN INC.; WO2009/17822; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem