Category: pyridine-derivatives

Application of 75806-86-9 ,Some common heterocyclic compound, 75806-86-9, molecular formula is C5H2BrClN2O2, 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 sodium hydride [(1 .52 g, 63.17 mmol (95%)] in DMSO (20.0 mL) at 0 00 diethylmalonate (10.11 g, 63.17 mmol) was added and kept for reflux at 100 00for 1 h. The reaction mixture was cooled to room temperature before drop wise addition of intermediate 32b (10.0 g, 42.11 mmol) in DMSO (20 mL) . The resultingmixture wasrefluxed at 100 00 for 3 h. The reaction mixture was quenched with ice water and extracted by using Ethyl acetate washed with water, and dried over anhydrous Na2SO4. The solvent was removed under vacuo to yield the title compound (10.0 g, 75.00%) as a brown oily product. LOMS: (M-H) = 315.0

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. 75806-86-9, 2-Bromo-5-chloro-3-nitropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; MADANAHALLI RANGANATH RAO, Jagannath; GURRAM RANGA, Madhavan; PACHIYAPPAN, Shanmugam; WO2014/202528; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 28733-43-9 , The common heterocyclic compound, 28733-43-9, name is 5-Bromonicotinamide, molecular formula is C6H5BrN2O, 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.

Step 1: 3-Amino-5-bromopyridine To a ice-cold solution of 31.8 g (0.79 mol) of Sodium hydroxide and 40.7 g (0.255 mol) of Bromine in 340 ml of water were added 42.0 g (0.209 mol) of commercially available 5-Bromonicotinamide. The mixture was allowed to warm up to room temperature and then heated for 1 h at 70 C. The resulting brown suspension was allowed to cool to room temperature. The aqueous phase was saturated with brine and extracted three times with a 1:1 mixture of THF and t-Butyl-methyl ether. The combined organic phases were dried over magnesium sulfate, filtered and concentrated in vaccuo. Concentration in vaccuo yielded 39.1 g of a dark brown residue which was purified by flash chromatography (heptane/ethyl acetate 1:1) to yield the title compound as a brown solid (total 70.2 g, 70%), MS (ISP): m/e=173.1, 175.1 (M+H+).

The synthetic route of 28733-43-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jaeschke, Georg; Kolczewski, Sabine; Porter, Richard Hugh Philip; Vieira, Eric; US2006/199960; (2006); A1;,
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. 131747-62-1, name is 3-(Trifluoromethyl)pyridine-2-carboxaldehyde. A new synthetic method of this compound is introduced below., SDS of cas: 131747-62-1

To a solution of 185 (50 mg, 0.2808 mmol) in toluene 15 ml was added 66 (68.8 mg, 0.393 mmol). PTSA (106.7 mg, 0.561 mmol) was added to the reaction mass and stirred at 120 C. for 6 h. The reaction mass was diluted with ethyl acetate and washed with water (3×25 ml.). The organic layer was dried over sodium sulphate and concentrated to get the crude 189, which was used for next step without further purification.

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, 131747-62-1, 3-(Trifluoromethyl)pyridine-2-carboxaldehyde.

Reference:
Patent; Vankayalapati, Hariprasad; Yerramreddy, Venkatakrishnareddy; US2015/72980; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 69045-78-9 ,Some common heterocyclic compound, 69045-78-9, molecular formula is C6H3Cl4N, 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 obtained 2-chloro-5-trichloromethylpyridine 46.2 g,After adding the catalyst, the temperature is raised to 150-160C.Slowly dry the chlorine gas for heavy chlorination.After 6 hours of reaction, dilute the reaction solution with benzene, wash with water and dry the organic phase.After evaporating the benzene under reduced pressure,After distillation, 50.3 g of oily product was obtained.That is the intermediate 2,3-dichloro-5-trichloromethylpyridine,The yield was 90% and the content was 95%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,69045-78-9, its application will become more common.

Reference:
Patent; Shandong Eastern Countries Nong Pharmaceutical Ji Industrial Co., Ltd.; Yu Lexiang; Li Yuan; Liu Weihua; Sun Meixin; Sun Fujiang; (7 pag.)CN106748985; (2017); A;,
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. 13466-35-8, name is 3-Chloro-2-hydroxypyridine, the common compound, a new synthetic route is introduced below. name: 3-Chloro-2-hydroxypyridine

Chlorination: 40 g of 3-chloro-2-hydroxypyridine and 100 g of dichloroethane,DMF0.3g,Phosphorus oxychloride 56g was added to the reaction flask and refluxed.In the control,After the reaction is over,Distilled ethylene dichloride,Slowly add cold water to the reaction solution.After fully hydrolyzing, adjust the pH to 4-5 and steam it.Get 2,3-dichloropyridine,Dry at room temperature and dry at 43gThe purity is 99.1%.

The synthetic route of 13466-35-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Suzhou Kaiyuan People’s Welfare Technology Co., Ltd.; Zhao Fei; Song Liang; Chen Wei; Wei Haihao; Zeng Miao; Xu Jianfeng; (8 pag.)CN107935921; (2018); 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. 97944-43-9, name is 3-Bromo-5-methylpyridin-4-amine. A new synthetic method of this compound is introduced below., Quality Control of 3-Bromo-5-methylpyridin-4-amine

A sealed tube was charged with 3-bromo-5-methylpyridin-4-amine [97944-43-9] (1.00 g, 4.26 mmol), isopropenylboronic acid pinacol ester [126726-62-3] (1.07 g, 6.34 mmol), Pd(PPh3)4 (507 mg, 0.43 mmol), l,4-dioxane (10 mL) and NaHCCL (sat., aq., 10 mL). The reaction mixture was stirred under reflux for 16 h, cooled down and diluted with water and DCM until clear phase separation. The aqueous phase was extracted with DCM. The combined organic extracts were dried (MgS04), filtered and concentrated in vacuo to afford 1-112 (1.77 g, 83%, 39% purity) which was sued as such in the next step

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, 97944-43-9, 3-Bromo-5-methylpyridin-4-amine.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BARTOLOME-NEBREDA, Jose Manuel; TRABANCO-SUAREZ, Andres, Avelino; TRESADERN, Gary John; MARTINEZ LAMENCA, Carolina; LEENAERTS, Joseph Elisabeth; OEHLRICH, Daniel; BUIJNSTERS, Peter Jacobus Johannes Antonius; VELTER, Adriana, Ingrid; VAN ROOSBROECK, Yves, Emiel, Maria; (171 pag.)WO2019/243535; (2019); 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.5453-67-8, name is Dimethyl pyridine-2,6-dicarboxylate, molecular formula is C9H9NO4, molecular weight is 195.17, as common compound, the synthetic route is as follows.Application In Synthesis of Dimethyl pyridine-2,6-dicarboxylate

A solution of compound 6 (9.75 g, 50 mmol) in absolute ethanol (40 ml)and stirred in an ice bath as 7.8 g (4 eq.) of sodium borohydride wasadded in portion over 15 minutes, and the mixture was stirred at 0 for1 hour. The ice bath was removed and stirred at room temperature for 2hours, after which it was heated at reflux on a steam bath for 10 hours.The solvent was distilled in vacuo, the residue was mixed with 40 mL ofacetone, and heated on a steam bath for 1 h, and the solvent was distilledin vacuo. The residue was mixed with 40 mL of aqueous potassiumcarbonate and heated on a steam bath for 1 h, the solvent was distilledin vacuo, and the residue was dissolved in 100 mL of water. The aqueous solution was extracted continuously with CHCl3 for 10h to give 6 g (87%)of compound 7. 1H NMR (400 MHz, CDCl3) delta 7.70 (t, J = 7.6 Hz, 1H),7.20 (d, J = 7.7 Hz, 2H), 4.78 (s, 4H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5453-67-8, Dimethyl pyridine-2,6-dicarboxylate, and friends who are interested can also refer to it.

Reference:
Article; Yu, Kang-Kang; Li, Kun; Hou, Ji-Ting; Yu, Xiao-Qi; Tetrahedron Letters; vol. 54; 43; (2013); p. 5771 – 5774;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1256805-54-5, Adding some certain compound to certain chemical reactions, such as: 1256805-54-5, name is 6-Chloro-4-methoxypyridin-3-amine,molecular formula is C6H7ClN2O, 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 1256805-54-5.

To a mixture of 6-chloro-4-methoxypyridin-3-amine (0.50 g, 3.1 mmol) andpotassium isothiocyanate (0.61 g, 6.3 mmol) in acetic acid (5 mL) at room temperature wasadded bromine (0.18 mL, 3.4 mmol) in acetic acid (2 mL) over 30 mm. The mixture wasstirred at room temperature for 16 h before additional potassium isothiocyanate (0.61 g, 6.3 mmol) and acetic acid (1 mL) were added. The mixture was stirred at room temperature for 24 h. To the mixture was added water (100 mL) and the mixture was stirred for 2 h. The insoluble material was collected by suction filtration and the filter cake was suspended in water (100 mL) and stirred for 2 h. The solid was collected by suction filtration and driedunder vacuum at 50 C to give 5-chloro-7-methoxythiazolo[5,4-bjpyridin-2-amine (0.70 g,3.1 mmol, 100% yield) as atan solid. MS (ESI)m/z: 215.9 [M+Hf 1H NMR (500 MI-Tz, DMSO-d6) oe 7.74 (br s, 2H), 7.02 (s, 1H), 3.94 (s, 3H).

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. 1256805-54-5, 6-Chloro-4-methoxypyridin-3-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; CARPENTER, Joseph E.; BROEKEMA, Matthias; FENG, Jianxin; LIU, Chunjian C.; WANG, Wei; WANG, Ying; (244 pag.)WO2019/89670; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 886365-46-4, 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 886365-46-4, name is 5-Chloro-3-methylpyridine-2-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

Synthesis of 5-chloro-3-methylpicolinamide The title compound was synthesized according to Method AA starting from 5-chloro-3-methylpicolinic acid (intermediate 6). MS m/z=171.1 [M+H]+. Calculated for C7H7ClN2O: 170

According to the analysis of related databases, 886365-46-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MINATTI, Ana Elena; LOW, Jonathan D.; ALLEN, Jennifer R.; CHEN, Jian; CHEN, Ning; CHENG, Yuan; JUDD, Ted; LIU, Qingyian; LOPEZ, Patricia; QIAN, Wenyuan; RUMFELT, Shannon; RZASA, Robert M.; TAMAYO, Nuria A.; XUE, Qiufen; YANG, Bryant; ZHONG, Wenge; US2014/249104; (2014); 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.160590-36-3, name is 2-Methoxy-3-nitro-4-methylpyridine, molecular formula is C7H8N2O3, molecular weight is 168.15, as common compound, the synthetic route is as follows.Formula: C7H8N2O3

Sodium acetate (365 g, 5.37 mol) was added to a stirred solution of 2-methoxy-4-methyl-3- nitropyridine (250 g, 1.49 mol) in acetic acid (1.5 L) at ambient temperature and then Br2 (639 g, 4.00 mol) was added dropwise (30 min). After addition, the mixture was heated at 80 C for 12 h, at which time TLC indicated the reaction had gone to completion. The mixture was cooled (0 C) and quenched by sequential addition of 10% aqueous (1.5 L) and saturated aqueous Na2S03 (1.5 L). The resulting solid was collected by filtration washed with water, and dried under reduced pressure to give the title compound (302 g, 82.2% yield) as a light yellow solid. 1H NMR (400 MHz, DMSO-t 6): delta 8.25 (s, 1 H), 3.94 (s, 3 H), 2.29 (s, 3 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,160590-36-3, 2-Methoxy-3-nitro-4-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; ALBRECHT, Brian, K.; BELLON, Steven, F.; BURDICK, Daniel, J.; COTE, Alexandre; CRAWFORD, Terry; DAKIN, Les, A.; HSIAO-WEI TSUI, Vickie; HEWITT, Michael, Charles; LEBLANC, Yves; MAGNUSON, Steven, R.; NASVESCHUK, Christopher, G.; ROMERO, F., Anthony; TANG, Yong; TAYLOR, Alexander, M.; WANG, Shumei; (251 pag.)WO2016/77375; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem