Month: April 2022

Adding a certain compound to certain chemical reactions, such as: 1796-84-5, 4-Ethoxy-3-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, 1796-84-5, blongs to pyridine-derivatives compound. Computed Properties of C7H8N2O3

Step 4: 1-N,N-Dimethylcarbamoyl-4-bromo-3-(4-(N-3-nitropyridin-4-yl)aminomethylbenzoyl)indole. A mixture of the 1-N,N-dimethylcarbamoyl-4-bromo-3-(4-aminomethylbenzoyl)indole prepared in step 3 (13.65 g) and 4-ethoxy-3-nitropyridine (5.10 g, 30.3 mmol) in CH3 CN (50 mL) was heated at reflux for 50 hours during which time 46 mL of solvent distilled out. To the thick residue was added toluene (50 mL) and the mixture was heated at a rate such that 21 mL of solvent distilled off over 2 hours. The reaction mixture was cooled to ambient temperature and diluted with ethyl acetate (30 mL). The solution was placed directly on a silica gel column and eluted with 50%, then 80% ethyl acetate/toluene to give 1-N,N-dimethylcarbamoyl-4-bromo-3-(4-(N-3-nitropyridin-4-yl)aminomethylbenzoyl)indole (6.76 g), mp 173.5-174.5 C. after crystallization from ethyl acetate/ether.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1796-84-5, its application will become more common.

Reference:
Patent; Abbott Laboratories; US5486525; (1996); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 185041-05-8, 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.185041-05-8, name is Methyl 2-chloro-4-iodonicotinate, molecular formula is C7H5ClINO2, molecular weight is 297.48, as common compound, the synthetic route is as follows.

Amixture of methyl 2-chloro-4-iodonicotinate (4.00 g, 13.5 mmol, prepared inStep 1 for 23),(2,5-difluorophenyl)boronic acid (2.19 g, 13.8 mmol), PdCl2(dppf)(0.984 g, 1.34 mmol) and K2CO3 (4.65 g, 33.6 mmol) indioxane (25 mL) and water (5 mL) was heated to 80 C and stirred for 12 h. Thereaction mixture was filtered to remove insoluble material. The filtrate wasdiluted with water (55 mL) and the mixture was extracted with EtOAc (2 x 30mL). The combined organic phase was washed with brine (40 mL), dried withanhydrous Na2SO4, filtered and concentrated invacuo. The residue was purified by flash column chromatography on silicagel (Petroleum ether/EtOAc = 100/1 to 30/1) to afford methyl2-chloro-4-(2,5-difluorophenyl)nicotinate (3.70 g, 87%) as a colorless oil. 1HNMR (400 MHz, CDCl3) delta 3.78 (3H, s), 7.00-7.07 (1H, m), 7.09-7.19(2H, m), 7.30 (1H, d, J = 5.2 Hz),8.52 (1H, d, J = 5.2 Hz). MS (ESI)m/z: 284.0 [M+H]+.

Statistics shows that 185041-05-8 is playing an increasingly important role. we look forward to future research findings about Methyl 2-chloro-4-iodonicotinate.

Reference:
Article; Miyazaki, Tohru; Kawasaki, Masanori; Suzuki, Atsushi; Ito, Yuki; Imanishi, Akio; Maru, Takamitsu; Kawamoto, Tomohiro; Koike, Tatsuki; Bioorganic and Medicinal Chemistry Letters; vol. 29; 6; (2019); p. 815 – 820;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 884494-45-5, 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. 884494-45-5, name is 2-Fluoro-4-iodo-6-methylpyridine. A new synthetic method of this compound is introduced below.

INTERMEDIATE 25 4-lodo-2-methvl-6-(propan-2-vloxv)pyridine A mixture of 2-fuoro-4-iodo-6-methylpyridine (0.20 g, 0.84 mmol), isopropanol (0.20 mL, 2.6 mmol) and sodium hydride (95%, 100 mg, 4.0 mmol) in diethyl ether (5 mL) was stirred at 23 C for 16 h. The reaction mixture was filtered through a plug of silica gel, eluting with diethyl ether, and the solvent was allowed to evaporate at atmospheric pressure to give the 78 title compound. MS: m/z = 278.2 (M + 1). 1H NMR (400 MHz, DMSO) 6 7.20 (dd, 1H, J = 1.2, 0.7 Hz), 6.96 (dd, 1H, J = 1.3, 0.7 Hz), 5.26-5.15 (m, 1H), 2.32 (s, 3H), 1.25 (d, 6H, J = 6.2 Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,884494-45-5, 2-Fluoro-4-iodo-6-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BELL, Ian, M.; ZHAO, Lianyun; FRALEY, Mark; ZHU, Cheng; BIFTU, Tesfaye; BRNARDIC, Edward Joseph; WANG, Cheng; ZARTMAN, C. Blair; GALLICCHIO, Steven; NGUYEN, Diem; CROWLEY, Brendan; POTTEIGER, Craig; (257 pag.)WO2016/22644; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 1003711-43-0, name is 2-Bromo-5-hydroxy-3-methylpyridine, molecular formula is C6H6BrNO, 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. HPLC of Formula: C6H6BrNO

6-Bromo-5-methylpyridin-3-ol (10.4 g, 55.3 mmol) and NCS (8.12 g, 60.8 mmol) in Nu,Nu-dimethylformamide (DMF) (150 mL) were heated at 80 C for 2 hours. The mixture was allowed to cool to room temperature, quenched with brine, and extracted 3 times with ethyl acetate. The combined organic layers were washed with 5% lithium chloride, washed with brine, dried over sodium sulfate, and concentrated. The residue was purified by silica chromatography eluting with a gradient of 0% to 50% ethyl acetate in hexanes. Fractions were concentrated to give 6-bromo-2-chloro-5-methylpyridin-3-ol (7.85 g, 35.3 mmol, 63.8 % yield) as a white powder. LCMS(ES+)(m/z) : 222, 224, 226 (M+1 ).

With the rapid development of chemical substances, we look forward to future research findings about 1003711-43-0.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; CATALANO, John G.; CHONG, Pek Yoke; DICKSON, Hamilton D.; LEIVERS, Martin R.; WEATHERHEAD, Jason Gordon; (186 pag.)WO2019/69293; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 67938-76-5 ,Some common heterocyclic compound, 67938-76-5, molecular formula is C6H7ClN2, 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 compound 2-(aminomethyl)-5-chloropyridine (18 g, 0.13 mol, from Step D) was dissolved in dichioromethane (50 mL) and hydrochloric methanol solution (5 M, 50 mL) was added. After stirring for several min a white solid began to precipitate. The mixture was stirred for 1 h at 0-5 °C, and the solid was collected by filtration and the filtrate was evaporated in vacuo to give some off-white solid. The combined solid was washed with a small amount of cold DCM. The product was dried in vacuo to yield the indicated compound as the hydrochloric salt. -NMR (DMSO-de, 400 MHz) 6 8.70 (s, 3H), 8.62 (s5 1H), 8.0 (dd, 7=2.5, 6 Hz, 1H), 7.60 (d, J=8.5 Hz, lH), 4.15 (m, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,67938-76-5, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; RAGHAVAN, Subharekha; STELMACH, John, E.; SMITH, Cameron, J.; LI, Hong; WHITEHEAD, Alan; WADDELL, Sherman, T.; CHEN, Yi-Heng; MIAO, Shouwu; ORNOSKI, Olga, A.; GARFUNKLE, Joie; LIAO, Xibin; CHANG, Jiang; HAN, Xiaoqing; GUO, Jian; GROEPER, Jonathan, A.; BROCKUNIER, Linda, L.; ROSAUER, Keith; PARMEE, Emma, R.; WO2011/149921; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 92992-85-3, 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 92992-85-3, name is 2-Bromo-3,5-dimethylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

(i) 2-Bromo-3,5-dimethylpyridine (12.7 g) 1,3-diaminopropane (31 ml) and pyridine (7.5 ml) were heated together under reflux for 12 hr. Working up the reaction as in the method of Example 14(i) gave 2-(3-aminopropylamino)-3,5-dimethylpyridine as an oil (2.45 g) which was used without further purification.

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 92992-85-3, 2-Bromo-3,5-dimethylpyridine.

Reference:
Patent; Smith Kline & French Laboratories Limited; US4548940; (1985); A;,
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. 58553-48-3, name is 5-(Hydroxymethyl)picolinonitrile. A new synthetic method of this compound is introduced below., Recommanded Product: 5-(Hydroxymethyl)picolinonitrile

Step 2: (0590) To a solution of 5-(hydroxymethyl)picolinonitrile (1.59 g, 11.9 mmol) in 80 mL of DCM was added diisopropylethylamine (3.2 mL), followed by a solution of methanesulfonyl chloride (1.49g, 13.0 mmol) in 20 mL of DCM at 0 C. The solution was stirred at 0 C. for 40 min and washed with 5% citric acid, sat. NaHCO3 (aq.) and brine. After concentration, the residue was purified by silica gel chromatography (elution with 0-30% EtOAc/Hex) to afford (6-cyanopyridin-3-yl)methyl methanesulfonate (2.33 g).

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, 58553-48-3, 5-(Hydroxymethyl)picolinonitrile.

Reference:
Patent; MERCK SHARP & DOHME CORP.; Scott, Jack D.; Stamford, Andrew W.; Gilbert, Eric J.; Cumming, Jared N.; Iserloh, Ulrich; Misiaszek, Jeffrey A.; Li, Guoqing; US2015/307465; (2015); A1;,
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.156072-84-3, name is 5-Chloro-2-cyano-3-methylpyridine, molecular formula is C7H5ClN2, molecular weight is 152.58, as common compound, the synthetic route is as follows.Computed Properties of C7H5ClN2

A mixture of 2-bromo-5-chloro-3-methylpyridine (45 g, 218 mmol), zinc cyanide (8.30 mL, 131 mmol), tris(dibenzylideneacetone) dipalladium (0) (4.99 g, 5.45 mmol), and 1 ,1?-bis(diphenylphosphino)ferrocene (6.04 g, 10.90 mmol) in dimethylacetamide (40 mL) was heated to 110 C for 4 h. The reaction mixture was cooled to RT, diluted with water and extracted with EtOAc. The organic phase obtained was concentrated under reduced pressure and residue purified by chromatography on silica gel using ISCO eluting with 0-60% EtOAc/hexanes to afford 5-chloro-3-methylpicolinonitrile (25.4 g, 166 mmol, 76 % yield). LC/MS (ESI+) m/z = 153.1 (M+H) . To a solution of 5-chloro-3-methylpicolinonitrile (24.0 g, 157 mmol) in EtOH (100 mL) was added NaOH (110 mL of 5 N solution, 550 mmol). The resulting mixture was refluxed at 90 C for 18 h. After cooling to RT, the reaction mixture was concentrated. The residue was diluted with water and the pH of the solution was adjusted to 4 by addition of 5 N HCl. The solid that precipitated was filtered and set aside. The filtrate was extracted with EtOAc (2 x). The aqueous layer was again acidified with 5 N HCl to pH 4 and extracted with EtOAc (2 x). The EtOAc extracts were combined, dried, and concentrated. The solid obtained from all the workup steps were combined and dried in a vacuum oven at 40 C for 12 h to give 5-chloro-3-methylpicolinic acid (268) (24.1 g, 140 mmol, 89% yield). LC/MS (ESI+) m/z = 172.0 (M+H) +. 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 11.29 (br. s., 1 H), 8.41 (d, J=1.76 Hz, 1 H), 7.73 (d, J=1.76 Hz, 1 H), 2.75 (s, 3 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,156072-84-3, 5-Chloro-2-cyano-3-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; AMGEN INC.; ALLEN, Jennifer R.; AMEGADZIE, Albert; BOURBEAU, Matthew P.; BROWN, James A.; CHEN, Jian J.; CHENG, Yuan; FROHN, Michael J.; GUZMAN-PEREZ, Angel; HARRINGTON, Paul E.; LIU, Longbin; LIU, Qingyian; LOW, Jonathan D.; MA, Vu Van; MANNING, James; MINATTI, Ana Elena; NGUYEN, Thomas T.; NISHMURA, Nobuko; NORMAN, Mark H.; PETTUS, Liping H.; PICKRELL, Alexander J.; QIAN, Wenyuan; RUMFELT, Shannon; RZASA, Robert M.; SIEGMUND, Aaron C.; STEC, Markian M.; WHITE, Ryan; XUE, Qiufen; (759 pag.)WO2016/22724; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 89364-04-5 , The common heterocyclic compound, 89364-04-5, name is 3-Bromo-4-nitropyridine, molecular formula is C5H3BrN2O2, 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: In a glovebox, K3PO4 (10 mol %, 5.3 mg), 18-Crown-6 (20 mol %, 13.2 mg) , and 2.5 mL tetrahydrofuran were added into a Schlenk tube equipped with a stir bar, then thiol (0.25 mmol) and nitrobenzene derivative (0.25 mmol) were added on the outside under an air atmosphere. The reaction mixture was stirred at room temperature 3 h (450 rpm). The resultant solution was concentrated and purified by silica gel column chromatography with EtOAc and petroleum ether as the eluent to give the corresponding thioether.

The synthetic route of 89364-04-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Xuan, Maojie; Lu, Chunlei; Lin, Bo-Lin; Chinese Chemical Letters; (2019);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 188577-68-6, 4,5-Dichloropyridin-2-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, Product Details of 188577-68-6, blongs to pyridine-derivatives compound. Product Details of 188577-68-6

Example 188 Synthesis of 6,7-dichloro-2-(chloromethyl)imidazo[1,2-a]pyridine. The mixture of 4,5-dichloropyridin-2-amine (1 g, 6.13 mmol) and 1,3-dichloropropan-2-one(10 g, 78.4 mmol) in DMF (20 mL) was stirred at 90 C. for 20 h. Then H2O (100 mL) was added and extracted with EtOAc (100 mL*2). The combined organic layers were concentrated to give the crude product which was purified by silica gel chromatography (PE/EtOAc=3/1) to give 6,7-dichloro-2-(chloromethyl)imidazo[1,2-a]pyridine (471 mg, yield: 33%) as a yellow solid. ESI-MS [M+H]+: 235.1

The synthetic route of 188577-68-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shire Human Genetic Therapies, Inc.; Papaioannou, Nikolaos; Fink, Sarah Jocelyn; Miller, Thomas Allen; Shipps, JR., Gerald Wayne; Travins, Jeremy Mark; Ehmann, David Edward; Rae, Alastair; Ellard, John Mark; (352 pag.)US2019/284182; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem