Category: pyridine-derivatives

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. 112110-07-3, name is 5-(Trifluoromethyl)pyridin-3-amine, the common compound, a new synthetic route is introduced below. Safety of 5-(Trifluoromethyl)pyridin-3-amine

To a stirred solution of Example 30A (100 mg, 0.62 mmol) and triethylamine (75 mg, 0.74 mmol) at0 C in dichloromethane (5 ml) is added ethyl malonyl chloride (108 mg, 0.65 mmol) dropwise over 15 minutes. The solution is allowed to warm to room temperature, and stirring is continued overnight (18 h). The crude reaction solution is concentrated in vacuo and the residue is purified by preparativeRP-HPLC (acetonitrile/water 1: 9 to 9: 1 gradient) to afford a colourless oil. Yield: 144.4 mg(85% of th.)HPLC (method 5): Rt = 3.80 min. , max 196 nm, 244 nm MS (ESIpos):m/z = 277[M+H] +H-NMR (300MHz, CDC13) :8 = 9.74 (s, 1H); 8.81 (s, 1H); 8.64 (s, 1H) ; 8.47 (s,1H) ; 4.30 (q, 2H); 3.53 (s, 2H);1. 35 (t, 3H) ppm.

The synthetic route of 112110-07-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER HEALTHCARE AG; WO2004/20410; (2004); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 100367-55-3 , The common heterocyclic compound, 100367-55-3, name is 5-Nitropicolinonitrile, molecular formula is C6H3N3O2, 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 mixture of X1 (149 mg, 1.0 mmol), NaOCH3 5.4 mg (0.1 mmol) and 10.0 mL CH3OH was placed in the 50 mL flask and reacted at 40 C for 1 h. Then methylaminoacetaldehyde dimethyl acetal 105.0 mg (1.0 mmol) and CH3COOH 0.5 mL were added into the reaction mixture refluxed for 30 min. After that CH3OH 5.0 mL and CH3COOH 1.0 mL were added to and refluxed for another 4.5 h. Then pH of the resulting mixture was adjusted to 10. The resulting precipitates were collected by filtration and washed with water (30 mL x 2) to give the crude material. The resulting crude material was purified by recrystallization with methanol to afford compound X2 133.0 mg (70.0 %). mp: 202-203 C. 1H NMR (300 MHz,DMSO-d6): delta 7.23 (s, 1H, CH-imidazole), 7.40 (s, 1H, CH-imidazole), 8.23 (d, 1H, 3-H, J = 8.8 Hz), 8.64 (dd, 1H, 4-H, J = 2.6 Hz and J = 8.8 Hz), 9.36 (d, 1H, 6-H, J = 2.6 Hz), 13.2 (s, 1H, NH-imidazole). IR (KBr): 3153, 3109, 1600, 1579, 1471, 1383, 1118, 858 cm-1.

The synthetic route of 100367-55-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jiao, Yu; Xin, Bo-Tao; Zhang, Yanmin; Wu, Jianbing; Lu, Xiaolin; Zheng, Ying; Tang, Weifang; Zhou, Xiang; European Journal of Medicinal Chemistry; vol. 90; (2015); p. 170 – 183;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 2369-19-9, 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 2369-19-9, name is 2-Fluoro-5-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of diisopropylamine (252 mL, 1.80 mmol) in anhydrous tetrahydrofuran (5 mL) was added under argon at 20 C, a 2.5 M solution of n-butyllithium in hexanes (719 mL, 1.80 mmol). After stirring at 20 C for 30 min, the reaction was cooled to 78 C, then a solution of 2-fluoro-5-methylpyridine (14) [27] (200 mg, 1.80 mmol) in anhydrous tetrahydrofuran (1 mL) was added over 10 min. The reaction was stirred at 78 C for 3.5 h, then a solution of iodine (457 mg, 1.80 mmol) in anhydrous tetrahydrofuran (1 mL) was added. The mixture was stirred at 78 C for additional 1 h, before quenching with a solution of water (2 mL) and tetrahydrofuran (10 mL). After warming to 0 C, the mixture was diluted with water (50 mL) and sodium bisulfite was added until a colorless solution was obtained. After extraction with dichloromethane (3 x 30 mL), the combined organic layers were dried over magnesium sulfate, filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (dichloromethane/cyclohexane, 5/5, v/v) to give 2-fluoro-3-iodo-5-methylpyridine (15) (275 mg, 1.16 mmol) as a colorless solid. Yield 65%; Rf (SiO2, dichloromethane/cyclohexane, 5/5, v/v) 0.21; mp 40-45 C; IR (KBr) nu 1049, 1379, 1446, 2930 cm-1; 1H NMR (200 MHz, CDCl3) delta 2.28 (s, 3H, CH3), 7.95 (m, 2H, H-4, H-6); 13C NMR (50 MHz, CDCl3) delta 17.0 (CH3), 75.4 (d, 2JC-F = 44 Hz, C-3), 132.7 (d, 4JC-F = 5 Hz, C-5), 146.8 (d, 3JC-F = 13 Hz, C-6), 150.4 (C-4), 160.4 (d, 1JC-F = 232 Hz, C-2); 19F NMR (470 Mz, CDCl3) 61.7; ESI-MS m/z 237.89 [M+H]+.

According to the analysis of related databases, 2369-19-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Billaud, Emilie M.F.; Maisonial-Besset, Aurelie; Rbah-Vidal, Latifa; Vidal, Aurelien; Besse, Sophie; Bequignat, Jean-Baptiste; Decombat, Caroline; Degoul, Francoise; Audin, Laurent; Deloye, Jean-Bernard; Dolle, Frederic; Kuhnast, Bertrand; Madelmont, Jean-Claude; Tarrit, Sebastien; Galmier, Marie-Josephe; Borel, Michele; Auzeloux, Philippe; Miot-Noirault, Elisabeth; Chezal, Jean-Michel; European Journal of Medicinal Chemistry; vol. 92; (2015); p. 818 – 838;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 75073-11-9, 5-Iodo-6-methylpyridin-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, 75073-11-9, blongs to pyridine-derivatives compound. Quality Control of 5-Iodo-6-methylpyridin-2-amine

To a suspension of 2 g of 5-iodo-6-methylpyridine-2-amine in 15 mL of dimethoxyethane are added 1.3 mL of ethyl bromopyruvate. The reaction mixture is stirred at 20 C. for 16 hours and then concentrated to dryness, taken up in 15 mL of ethanol, refluxed for 2.5 hours and finally concentrated under reduced pressure. The residue is taken up in a mixture of dichloromethane and saturated sodium bicarbonate solution. The organic phase is dried over magnesium sulfate and concentrated to dryness under reduced pressure to give 2.77 g of ethyl 6-iodo-5-methyl(pyrid-2-yl)imidazo[1,2-a]pyridine-2-carboxylate in the form of a beige-coloured solid.1H NMR spectrum (DMSO-d6, delta in ppm): 1.33 (t, J=7.1 Hz, 3H), 2.84 (s, 3H), 4.33 (q, J=7.1 Hz, 2H), 7.34 (d, J=9.3 Hz, 1H), 7.66 (d, J=9.3 Hz, 1H), 8.48 (s, 1H).Mass spectrum (LC-MS-DAD-ELSD): m/z 331 [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,75073-11-9, its application will become more common.

Reference:
Patent; sanofi-aventis; US2010/317675; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 6515-09-9, name is 2,3,6-Trichloropyridine. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C5H2Cl3N

In a 1000 ml stainless steel autoclave, 50 g of 2,3,6-trichloropyridine was added.300g of methanol, 35g of triethylamine, and then added 0.05g of 10% palladium carbon.First replace the air in the kettle three times with nitrogen, and then replace it three times with hydrogen.Pressurize to 4.0Mpa and control the temperature at 45~50C.The reaction speed was set to 300 rpm/min, and hydrogen was continuously added during the reaction.The reaction pressure was maintained at 3.0 to 4.0 MPa, and the reaction was stopped after 4 hours of reaction.Cooling, sampling for liquid phase quantitative detection and analysis,The conversion rate of raw material 2,3,6-trichloropyridine is 96.5%.The selectivity to 2,3-dichloropyridine was 86.7%. After filtering the reaction solution,After rectifying and removing the reaction solvent, after adding a moisture layer,The organic phase was subjected to rectification to obtain 33.1 g of a white 2,3-dichloropyridine product.The product purity is 99.5%.

With the rapid development of chemical substances, we look forward to future research findings about 6515-09-9.

Reference:
Patent; Chongqing Zhong Bang Technology Co., Ltd.; Wang Ping; Lai Ming; Mu Xinbin; Jiang Cheng; Li Xueping; (5 pag.)CN109280026; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 58483-98-0, 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. 58483-98-0, name is 2-Amino-5-bromonicotinamide. A new synthetic method of this compound is introduced below.

Oxalyl chloride (100 mL, 1.16 mmol) was added dropwise to a suspension of 2- amino-5-bromo-nicotinamide (500 mg, 2.31 mmol) in toluene (5 mL) and the resulting mixture was heated to reflux for 4 h. The reaction mixture was cooled and the mustard- colored solid which had formed was collected by filtration. The solid was washed with a small amount of water, MEOH, and then dried under high vacuum (40 C) overnight to give the title compound (435 mg, 77%) :’H NMR (300 MHz, DMSO-D6) 8 11.86 (s, 1H), 11.60 (s, 1H), 8.72 (d, J = 2.5 Hz, 1H), 8. 35 (d, J = 2.5 Hz, 1 H) ; 13C NMR (126 MHz, DMSO-d6) 8 161.4, 154.8, 151.2, 150.17, 137.8, 112.6, 111.6.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,58483-98-0, 2-Amino-5-bromonicotinamide, and friends who are interested can also refer to it.

Reference:
Patent; AFFINIUM PHARMACEUTICALS, INC.; WO2004/52890; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1111637-74-1 , The common heterocyclic compound, 1111637-74-1, name is 1-(5-Bromo-2-fluoropyridin-3-yl)ethanone, molecular formula is C7H5BrFNO, 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: 1-(5-bromo-2-fluoropyridin-3-yl)-2-fluoroethanone (12a) A solution of 1-(5-bromo-2-fluoropyridin-3-yl)ethanone (200 mg, 0.92 mmol) and triethylamine (140 mul, 1.01 mmol) in toluene (2 mL) was treated with trimethylsilyl trifluoromethanesulfonate (182 mul, 1.01 mmol) under nitrogen atmosphere. The reaction mixture was heated to 80 C. for 2 h, the upper toluene phase was isolated (e.g. by decanting) and concentrated under reduced pressure to give a yellow oil. The oil was dissolved in acetonitrile (2 mL) and added to a suspension of 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo-(2.2.2)octane bis(tetrafluoroborate) (325 mg, 0.92 mmol) in acetonitrile (2 mL) at room temperature. After 1 h, the solvent was removed under reduced pressure. The residue was partitioned between brine and EtOAc. The organic phase was separated and dried over MgSO4. The solvent was removed under reduced pressure to obtain 1-(5-bromo-2-fluoropyridin-3-yl)-2-fluoroethanone (170 mg, 0.72 mmol, 79% yield, 90% purity) as a light yellow solid. This material was used in the next step without purification. MS m/z=237.9 [M+H]+. Calculated for C7H4BrF2NO: 236.01.

The synthetic route of 1111637-74-1 has been constantly updated, and we look forward to future research findings.

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

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. 884495-30-1, name is 5-Fluoro-2-methoxyisonicotinic acid. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 5-Fluoro-2-methoxyisonicotinic acid

(5-Fluoro-2-methoxy-pyridin-4-yl)methanol, used as starting material was prepared as follows:-Borane-tetrahydrofuran complex (1M solution in THF, 52.6 ml, 52.6 mmol) was added slowly to a solution of 5-fluoro-2-methoxy-pyridine-4-carboxylic acid (2 g, 11.7 mmol) in THF (100 ml) under nitrogen. The reaction mixture was stirred at room temperature for 2.5 h. The solvent was then evaporated and the residue was stirred in methanol (40 ml) for 16 h. The solvent was evaporated and the residue was purified on a silica isolute column, eluting with 0-1% MeOH in DCM to afford (5-fluoro-2-methoxy-pyridin-4-yl)methanol as a white solid (1.42 g, 77% yield).1H NMR (399.902 MHz, CDCl3) delta 3.90 (s, 3H), 4.76 (s, 2H), 6.84-6.87 (m, 1H), 7.92 (d, 1H). MS: m/z 158 (MH+); (5-Fluoro-2-methoxy-pyridin-4-yl)methanol, used as starting material, was prepared as follows:-Borane-tetrahydrofuran complex (IM solution in THF, 52.6 ml, 52.6 mmol) was added slowly to a solution of 5-fluoro-2-methoxy-pyridine-4-carboxylic acid (2 g, 11.7 mmol) in THF (100 ml) under nitrogen. The reaction mixture was stirred at room temperature for 2.5 h. The solvent was evaporated and the residue was stirred in methanol (40 ml) for 18 h. The solvent was evaporated and the crude product was purified by silica column chromatography, eluting with 0-1% MeOH in DCM. Pure product fractions were combined and evaporated to afford (5-fluoro-2-methoxypyridin-4-yl)methanol as a white solid (1.42 g, 77%).1H NMR (399.902 MHz, CDCl3) delta 3.90 (s, 3H), 4.76 (s, 2H), 6.84-6.87 (m, 1H), 7.92 (d, 1H); m/z (ES+) [M+H]+=158.

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, 884495-30-1, 5-Fluoro-2-methoxyisonicotinic acid.

Reference:
Patent; ASTRAZENECA AB; US2008/4302; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 99368-68-0, name is 6-Chloro-5-(trifluoromethyl)pyridin-3-amine. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 6-Chloro-5-(trifluoromethyl)pyridin-3-amine

D. lambda/-(5-bromo-3-(trifluoromethyl)pyridin-2-yl)acetamideA mixture of 6-chloro-5-(trifluoromethyl)pyridin-3-amine (2.95 mmol, 0.58 g) and 30% HBr in acetic acid (6 ml) in a sealed tube was heated at 1000C overnight. The crude mixture was poured into ice water, the pH was set to10 with 2N aqueous NaOH and extracted withCHCI3.The solvent was removed under reduced pressure to afford 0.680 g (82% of yield) of the expected product.ESI/MS (m/e, %): 281.96 (100.0%), 283.96 (97.3%).

With the rapid development of chemical substances, we look forward to future research findings about 99368-68-0.

Reference:
Patent; LABORATORIOS ALMIRALL, S.A.; WO2009/21696; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 169205-95-2, name is 2-(Methylthio)oxazolo[4,5-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows. name: 2-(Methylthio)oxazolo[4,5-b]pyridine

10161] 3-Methyl-2-methylthiooxazolopyridinium tosylateprepared by heating the corresponding 2-methylthioox- azolopyridines (M. Y. Chu-Moyer and R. l3erger, J. Org. Chem., 60, 5721-5725 (1995)) with one equivalent of methyl tosylate at 100-110 C. for one hout Derivatives preparedsimilarly include:

With the rapid development of chemical substances, we look forward to future research findings about 169205-95-2.

Reference:
Patent; LIFE TECHNOLOGIES CORPORATION; LEUNG, Wai-Yee; CHEUNG, Ching-Ying; YUE, Stephen; US2015/218380; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem