Day: April 6, 2022

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

Electric Literature of 1044872-40-3 ,Some common heterocyclic compound, 1044872-40-3, molecular formula is C7H6Cl2N2O2, 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.

In a 500-mL flask with a reflux condenser was added methyl 2-amino-4.6-dichloropyridine-3-carboxylate (22.5 g, 0.101 mol) and 25 wt % sodium methoxide in methanol (88 mL, 0.407 mol), together with methanol (20 mL). The mixture was heated to reflux for 5 hours, then cooled to room temperature. Acetic acid (15 mL) was added to the mixture and pH was adjusted to approximately 7. Methanol was removed and the residue was poured into water (100 mL). The precipitated solid was filtered and further rinsed with water (3*200 mL) to give methyl 2-amino-4,6-dimethoxypyridine-3-carboxylate (18.5 g, 86.4%)

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. 1044872-40-3, Methyl 2-amino-4,6-dichloronicotinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; RVX Therapeutics Inc.; McLure, Kevin G.; Young, Peter R.; US2013/281398; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 1033203-41-6, name is 6-Bromopyridine-3,4-diamine, the common compound, a new synthetic route is introduced below. Recommanded Product: 6-Bromopyridine-3,4-diamine

To a stirred solution of 6-bromopyridine-3,4-diamine (1.5 g, 8 mmol) in triethylorthoformate (7.11 g, 48 mmol) was added acetic anhydride (7.35 g, 72 mmol)) and stirred at 90C for 6h. The reaction mixture was cooled and evaporated to dryness, then 10 mL 10N NaOH solution was added and heated the contents at 60 C for 50 min. After reaction mixture was cooled acidified with AcOH to a pH 6, then added crushed ice stirred for 15 minutes precipitated solid was filtered. The precipitated solid was washed with n-pentane to get 6-bromo-3H- imidazo[4,5-c]pyridine (1.5 g, 94%) as pale brown solid. LC-MS (method 32): Rt = 0.26 min; m/z = 198.0 (M+H+).

The synthetic route of 1033203-41-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ORYZON GENOMICS, S.A.; SALAS SOLANA, Jorge; CARCELLER GONZALEZ, Elena; ORTEGA MUNOZ, Alberto; (195 pag.)WO2018/149986; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 940911-03-5 ,Some common heterocyclic compound, 940911-03-5, molecular formula is C8H5NO, 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.

C . 5 – { [4-(5 ,5 -Dimethyl- 1 ,3 ,2-dioxaborinan-2-yl)phenyl] ethynyl} pyridine -2- carbaldehyde; To an argon purged solution of 2-(4-iodophenyl)-5,5-dimethyl-l,3,2- dioxaborinane (Method 3, step A) (15 g, 48 mmol) in acetonitrile was addedPdCl2(PPh3)2 (0.7 g, 9.5 mmol) and CuI (0.09 g, 4.7 mmol) at room temperature. The resulting solution was stirred under argon for 10 min. Triethylamine (20 mL, 142 mmol) followed by 5-[(trimethylsilyl)ethynyl]pyridine-2-carbaldehyde (8.1 g, 62mmol) were added and the reaction mixture was then stirred at 85 0C for 2 h. The reaction mixture was concentrated under reduced pressure and then ice-cold water was added. The precipitated solid was stirred as a suspension and was then filtered and washed with water followed by pet-ether to provide 5-{[4-(5,5-dimethyl-l,3,2-dioxaborinan-2- yl)phenyl]ethynyl}pyridine-2-carbaldehyde (15 g, 99%) as brown solid. LC-MS: [M+H]+ 3201H NMR (400 MHz, CDCl3) delta: ppm 10.08 (s, IH), 8.89 (s, IH), 7.95 (m, 2H), 7.82 (d, 2H), 7.55 (d, 2H), 3.78 (s, 4H), 1.03 (s, 6H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,940911-03-5, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BENENATO, Kerry, Ellen; CHOY, Allison, Laura; HALE, Michael, Robin; HILL, Pamela; MARONE, Valerie; MILLER, Matthew; WO2010/100475; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 60154-05-4 ,Some common heterocyclic compound, 60154-05-4, molecular formula is C6H6INO, 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: A mixture of potassium fluoride (0.15g, 2.6mmol) and copper iodide (I) (0.50g, 2.6mmol) was heated under reduced pressure until a greenish color appeared, and after cooling to rt, an iodo compound (1.0mmol) in DMF/HMPA (2.5mL each) and trimethyl(trifluoromethyl)silane (0.38mL, 2.6mmol) were added to this flask successively. The mixture was stirred for the specified time and at the indicated temperature (see Table 2). After quenching with satd aqueous ammonium chloride, usual workup and purification by silica gel chromatography yielded the trifluoromethylated product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,60154-05-4, its application will become more common.

Reference:
Article; Kawasaki-Takasuka, Tomoko; Yamazaki, Takashi; Tetrahedron; vol. 71; 38; (2015); p. 6824 – 6831;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem