Month: February 2022

Adding a certain compound to certain chemical reactions, such as: 99368-68-0, 6-Chloro-5-(trifluoromethyl)pyridin-3-amine, 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, 99368-68-0, blongs to pyridine-derivatives compound. Quality Control of 6-Chloro-5-(trifluoromethyl)pyridin-3-amine

Reference Example 121 6-chloro-2-methylpyridine-3-sulfonyl chloride; Under ice-cooling, thionyl chloride (4 mL) was added dropwise to water (24 mL) over 20 min. The mixture was stirred at room temperature for 12 hr to give a sulfur dioxide-containing solution. Separately, to the concentrated hydrochloric acid (6 mL) was added 5-amino-2-chloro-6-methylpyridine (1.0 g) with stirring under ice-cooling, and a solution of sodium nitrite (0.5 g) in water (2 mL) was added dropwise over 10 min. The reaction mixture was gradually added at 5 C. to the above-mentioned sulfur dioxide-containing solution added with cuprous chloride (10 mg). Under ice-cooling, the mixture was further stirred for 30 min, and the precipitate was collected by filtration, and washed with water to give the title compound as a pale-yellow solid (yield 1.1 g, 67%). 1H-NMR (CDCl3) delta: 2.99 (3H, s), 7.41 (1H, dd, J=8.7, 0.9 Hz), 8.26 (1H, d, J=8.4 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,99368-68-0, its application will become more common.

Reference:
Patent; Takeda Pharmaceutical Company Limited; US2007/60623; (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. 178876-83-0, name is Methyl 6-amino-3-bromopicolinate. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 178876-83-0

Example 158D methyl 3-bromo-6-fluoropicolinate To a solution of nitrosonium terafluoroborate (17.8 g) in dichloromethane (100 mL) at 5 C. was added EXAMPLE 158C (26.1 g) in dichloromethane (250 mL) over 1 hour. The reaction mixture was stirred an for additional 30 minutes at 5 C., and then allowed to warm to room temperature overnight. The reaction mixture was quenched with pH 7 buffer (100 mL), and then neutralized with solid potassium carbonate. The resulting mixture was extracted with ether (twice), and the combined extracts were washed with brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography on silica gel eluting with 1 to 10% ethyl acetate in hexanes to provide the title compound.

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, 178876-83-0, Methyl 6-amino-3-bromopicolinate.

Reference:
Patent; AbbVie Inc.; Wang, Le; Doherty, George; Wang, Xilu; Tao, Zhi-Fu; Bruncko, Milan; Kunzer, Aaron R.; Wendt, Michael D.; Song, Xiaohong; Frey, Robin; Hansen, Todd M.; Sullivan, Gerard M.; Judd, Andrew; Souers, Andrew; US2013/96121; (2013); 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. 327056-62-2, name is 2-Cyano-5-fluoropyridine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 2-Cyano-5-fluoropyridine

2) 2-[(5-Fluoropyridine-2-carbonyl)amino]malonic acid diethyl ester The above 5-fluoropyridine-2-carbonitrile (11.8 g) in 6N HCl (100 mL) was refluxed for 4 hours and then cooled in air. NaCl was added to the reaction mixture to saturate the mixture, and ethyl acetate was added thereto for partitioning the mixture. The organic layer was dried over sodium sulfate anhydrate. After a filtration step, the solvent was removed under reduced pressure, and the residue was dissolved in N,N-dimethylformamide (140 mL). 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (6.0 g), 1-hydroxybenzotriazole (770 mg), and aminomalonic acid diethyl ester hydrochloride (7.2 g) were added to the solution, and the mixture was stirred for 19.5 hours at room temperature. The reaction mixture was partitioned between water and ethyl acetate, and the organic layer was washed with saturated brine and then dried over sodium sulfate anhydrate. After a filtration step, the solvent was removed under reduced pressure, and the residue was purified through silica gel column chromatography (hexane – ethyl acetate), to thereby give 2-[(5-fluoropyridine-2-carbonyl)amino]malonic acid diethyl ester as a solid product (9.4 g, 53%). 1H-NMR (400MHz, CDCl3) delta:1.33 (6H, t, J=7.1Hz), 4.27-4.38(4H,m), 5.36 (1H, d, J=7.4Hz), 7.51-7.56 (1H, m), 8.20-8.21 (1H, m), 8.46 (1H, d, J=2.7Hz), 8.74 (1H, d, J=10.0Hz).

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, 327056-62-2, 2-Cyano-5-fluoropyridine.

Reference:
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1621537; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 65147-89-9, 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.65147-89-9, name is 6-Bromo-2-phenyl-1H-imidazo[4,5-b]pyridine, molecular formula is C12H8BrN3, molecular weight is 274.12, as common compound, the synthetic route is as follows.

Example 223 Under an argon stream, a mixture of 6-bromo-2-phenyl-1H-imidazo[4,5-b]pyridine (Compound of Reference Example 3) (90 mg), phenylboric acid (104 mg), tetrakis(triphenylphosphine)palladium(0) (38 mg), 2 M sodium carbonate (0.82 ml) and tetrahydrofuran (3.3 ml) was stirred at 85C for 24 hours.. The mixture was distributed into ethyl acetate – tetrahydrofuran (3: 1, v/v) and water.. The organic layer was washed with water and dried over MgSO4, and the solvent was distilled off under reduced pressure.. The residue was subjected to silica gel column chromatography, and the fraction eluted with ethyl acetate – chloroform – hexane (1: 1: 4, v/v) was concentrated under reduced pressure.. The resulting crystals were collected by filtration to obtain 2,6-diphenyl-1H-imidazo[4,5-b]pyridine (20 mg, 22 %).. The crystals were recrystallized from chloroform – methanol. HPLC (220 nm) Purity 97 % (Retention time 2.78 minutes) MS (ESI+, m/e) 272 (M+1)

Statistics shows that 65147-89-9 is playing an increasingly important role. we look forward to future research findings about 6-Bromo-2-phenyl-1H-imidazo[4,5-b]pyridine.

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1460067; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 195044-14-5, 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 195044-14-5, name is 2-Bromo-6-tert-butylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

Step-3: Synthesis of 2-tert-butyl-1-(6-tert-butylpyridin-2-yl)-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one To a stirred solution of 2-tert-butyl-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one (180 mg, 0.756 mmol, 1.0 eq) and 2-bromo-6-tert-butylpyridine (194.3 mg, 0.907 mmol, 1.2 eq) in 1,4 dioxane (5 mL) was added potassium carbonate (208.9 mg, 1.512 mmol, 2.0 eq) and the resulting mixture was purged with nitrogen for 30 min followed by addition of copper iodide (28.7 mg, 0.151 mmol, 0.2 eq), and N,N’-dimethylethylenediamine (DMEDA) (26.05 mg, 0.302 mmol, 0.4 eq) and again purged with nitrogen for 10 min. The resultant mixture was heated at 100 C. for 5 h. The reaction was monitored by TLC. After completion of reaction, the reaction mixture was diluted with water and extracted with EtOAc (50 mL*2). Combined organic layer was washed with water (50 mL) brine solution (50 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford crude which was purified by flash chromatography (Teledyne Isco Rf+); compound eluting 30% EtOAc/Hexane to afford 2-tert-butyl-1-(6-tert-butylpyridin-2-yl)-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one (100 mg, 35.71%) as off white solid.

According to the analysis of related databases, 195044-14-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; giraFpharma LLC; Chakravarty, Sarvajit; PHAM, Son Minh; Kankanala, Jayakanth; AGARWAL, Anil Kumar; PUJALA, Brahmam; SONI, Sanjeev; ARYA, Satish K.; PALVE, Deepak; Gupta, Ashu; KUMAR, Varun; (498 pag.)US2019/106427; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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;,
Pyridine – Wikipedia,
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