Tag: M.W:100-200

Reference of 18368-73-5 , The common heterocyclic compound, 18368-73-5, name is 3-Methyl-2-nitropyridine, molecular formula is C6H6N2O2, 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: To a stirred mixture of 1.00 mmol of nitropicoline 35 or 63, 1.20 mmol of the appropriate benzaldehyde, and 1.5 mmol of Huenig’s base in THF (7 mL/g of nitropicoline 35/63) was added 1.3 mmol of a 1 M THF solution of TBAF. The resulting mixture was heated 60 C for 1.5e2.0 h in the case of 2,3-dihydrofuro[3,2-c] pyridines or for 18 h in the case of 2,3-dihydrofuro[2,3-b]pyridines. After cooling to room temperature, the reactions were quenched with sat. aqueous NH4Cl. The solution was extracted with EtOAc, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel chromatography as specified above.

The synthetic route of 18368-73-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kuethe, Jeffrey T.; Tetrahedron; vol. 75; 34; (2019);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 823-61-0, 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. 823-61-0, name is 3,6-Dimethyl-2-pyridinamine. A new synthetic method of this compound is introduced below.

2) The obtained solution of O-(mesitylsulfonyl)hydroxylamine was added dropwise to a solution of commercially available 3,6-dimethyl-2-pyridinamine (16.4 g, 117 mmol) in DCM (100 mL) cooled in an ice bath. The mixture was then warmed to room temperature over 15 minutes. LCMS indicated almost complete conversion to the aminated intermediate.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,823-61-0, 3,6-Dimethyl-2-pyridinamine, and friends who are interested can also refer to it.

Reference:
Patent; H. Lundbeck A/S; Kehler, Jan; Bang-Andersen, Benny; US2013/303770; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 135450-23-6, 6-(Chloromethyl)-2-cyanopyridine, 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, 135450-23-6, blongs to pyridine-derivatives compound. Quality Control of 6-(Chloromethyl)-2-cyanopyridine

Reference Example 150-1 tert-Butyl {2-[1-(6-cyanopyridin-2-ylmethyl)-2-(1-methylcyclopropyl)-2-oxoethyl]-5-methoxyphenyl}carbamate Under an argon atmosphere, to a solution of tert-butyl {5-methoxy-2-[2-(1-methylcyclopropyl)-2-oxoethyl]phenyl}carbamate (300 mg) in N,N-dimethylformamide (3.1 mL) was added sodium hydride (50-72% in oil, 50 mg) under ice-cooling, and the mixture was stirred for 1 hour. 6-(Chloromethyl)pyridine-2-carbonitrile (158 mg) was added thereto in one portion, and the mixture was gradually warmed to room temperature. 13 Hours later, to the reaction mixture were added a saturated aqueous ammonium chloride solution and water, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine successively, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (271 mg). 1H-NMR (CDCl3) delta ppm: 0.62-0.73 (2H, m), 1.22-1.30 (5H, m), 1.57 (9H, s), 3.21 (1H, dd, J=8.2, 15.7 Hz), 3.54 (1H, dd, J=6.7, 15.7 Hz), 3.78 (3H, s), 4.68-4.78 (1H, m), 6.54-6.61 (1H, m), 6.95 (1H, d, J=8.5 Hz), 7.18-7.25 (1H, m), 7.33-7.40 (1H, m), 7.48-7.55 (1H, m), 7.64 (1H, t, J=7.8 Hz), 7.82 (1H, br s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,135450-23-6, its application will become more common.

Reference:
Patent; Tatani, Kazuya; Kondo, Atsushi; Kondo, Tatsuhiro; Kawamura, Naohiro; Seto, Shigeki; Kohno, Yasushi; US2013/317065; (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. 67367-24-2, name is Methyl 4-hydroxynicotinate, the common compound, a new synthetic route is introduced below. Product Details of 67367-24-2

A solution of the required alcohol (0.30 mmol; 3 eq.) in DMF (0.2 mL), in a glass vial under inert atmosphere (N2), is treated with NaH (3.3 eq.) at rt. After 10 min, it is treated with a solution of the chloride (0.10 mmol; 1 eq.) in DMF (0.8 mL) and the reaction mixture is stirred at rt and monitored by LC-MS. Upon reaction completion, the reaction mixture is either treated with silica gel-supported sulfonic acid (5.0 eq.; Silicycle SiliaBond Tosic Acid; SCX; R60530B; 0.8 mmol/g), shaken 1 h at rt and filtered, or loaded on a corresponding cartridge (Silicycle SiliaPrep Tosic Acid Si-SCX). In both cases, the resin is then washed with DCM, 1 : 1 DCM/MeOH and MeOH, and the product eventually released from the resin with Mu ammonia solution in MeOH. The solution of crude product is concentrated under reduced pressure and purification of the residue gives the desired product. Starting from the compound of Preparation R and methyl 4-hydroxynicotinate and proceeding in analogy to Procedure AC, the title compound was obtained, after purification by prep-HPLC (acidic conditions) and treatment with HC1, as an amorphous solid (21% yield).MS (ESI, m/z): 381.28 [M+H+].

The synthetic route of 67367-24-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; BUR, Daniel; GUDE, Markus; HUBSCHWERLEN, Christian; PANCHAUD, Philippe; WO2011/121555; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 98121-41-6, 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 98121-41-6, name is 3-Amino-5,6-dichloropyridine. This compound has unique chemical properties. The synthetic route is as follows.

Example 2D 5-bromo-2,3-dichloropyridine A 5 L flask with mechanical stirrer, thermocouple, and addition funnel was charged with the product of Example 2C (70 g, 429 mmol) and 48% HBraq (240 mL). The suspension was maintained at 0-5 C. as a solution of NaNO2 (32.0 g, 464 mmol) in water (100 mL) was added dropwise over 1 hour. Additional water (200 mL) was added and the mixture was stirred for 10 minutes at 0-5 C. The mixture was treated with CuBr (32.6 g, 227 mmol) in portions over 20 minutes followed by additional water to maintain a fluid reaction mixture. The mixture was allowed to warm to room temperature and diluted with water. The mixture was distilled at ambient pressure, until the distillate ran clear (1.5 L collected). The distillate was extracted with EtOAc (3*500 mL) and the combined extracts were washed with brine (100 mL), dried (MgSO4), and concentrated to provide 5-bromo-2,3-dichloropyridine as a solid. 1H NMR (CDCl3, 300 MHz) delta 7.94 (d, J=3 Hz, 1H), 8.38 (d, J=3 Hz, 1H).

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 98121-41-6, 3-Amino-5,6-dichloropyridine.

Reference:
Patent; Buckley, Michael J.; Ji, Jianguo; US2005/261348; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 886365-46-4, Adding some certain compound to certain chemical reactions, such as: 886365-46-4, name is 5-Chloro-3-methylpyridine-2-carboxylic acid,molecular formula is C7H6ClNO2, 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 886365-46-4.

Step 3: (R)-N-(3-(8-amino-6-(fluoromethyl)-4,4-dioxido-4-thia-7-azaspiro[2.5]oct-7-en-6-yl)-4-fluorophenyl)-5-chloro-3-methylpicolinamide To a stirred mixture of (R)-8-amino-6-(5-amino-2-fluorophenyl)-6-(fluoromethyl)-4-thia-7-azaspiro[2.5]oct-7-ene 4,4-dioxide (0.0625 g, 0.198 mmol) and 5-chloro-3-methylpicolinic acid (0.036 g, 0.208 mmol) in DCM (3 mL) was added 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (0.378 g, 0.595 mmol). After the addition, the mixture was stirred at RT for 16 h, saturated aqueous NaHCO3 was added, layers were separated, organic phase dried over Na2SO4, concentrated and purified by silica gel chromatography (30% EtOAc/DCM) to give the title compound as an off white solid (51 mg, 55%). LC/MS (ESI+) m/z: 469 (M+H). 1H NMR (400 MHz, CHLOROFORM-d) ppm 10.01 (1H, s), 8.35-8.43 (1H, m), 7.96 (1H, ddd, J=8.8, 4.3, 2.8 Hz), 7.63-7.68 (2H, m), 7.09 (1H, dd, J=11.7, 8.8 Hz), 4.82 (1H, dd, J=14.7, 8.8 Hz), 4.55 (1H, dd, J=14.7, 8.8 Hz), 4.45 (2H, br. s.), 3.77 (2H, dd, J=14.5, 8.8 Hz), 2.79 (3H, s), 1.73-1.86 (2H, m), 1.56 (2H, m).

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. 886365-46-4, 5-Chloro-3-methylpyridine-2-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; LEWIS, Richard T.; ALLEN, Jennifer R.; CHENG, Yuan; CHOQUETTE, Deborah; EPSTEIN, Oleg; GUZMAN-PEREZ, Angel; HARRINGTON, Paul E.; HUA, Zihao; HUNGATE, Randall W.; HUMAN, Jason Brooks; JUDD, Ted; LIU, Qingyian; LOPEZ, Patricia; MINATTI, Ana Elena; OLIVIERI, Philip; ROMERO, Karina; RUMFELT, Shannon; RZASA, Robert M.; SCHENKEL, Laurie; STELLWAGEN, John; WHITE, Ryan; XUE, Qiufen; ZHENG, Xiao; ZHONG, Wenge; US2014/107109; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 94220-38-9, 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. 94220-38-9, name is 7-Chloro-5-methyl-1H-pyrazolo[4,3-b]-pyridine, molecular formula is C7H6ClN3, 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.

EXAMPLE 1 7-Allylamino-5-methyl-1H-pyrazolo[4,3-b]pyridine (E1) STR15 A mixture of 7-chloro-5-methyl-1H-pyrazolo[4,3-b]pyridine (D4) (1.0 g, 0.006 mole) and allylamine (60 g) in water (100 ml) was heated under reflux for 12 days. On cooling the reaction mixture was evaporated to dryness, basified to pH8 with 10% sodium carbonate solution and the resulting solid filtered off. Recrystallisation from chloroform/pentane gave the product as white solid (1.0 g). m.p. 172-174 C. delta(d6 DMSO): 2.40 (3H, s); 3.91 (2H, d, J=6.5 Hz); 3.4-5.0 (1H, br.s exchanges with D2 O); 5.00-5.50 (2H, m); 5.68-6.05 (1H, m); 6.15 (1H, s); 6.4-6.7 (1H, br.s exchanges with D2 O); 7.85 (1H, s). Found: C, 63.57; H, 6.35; N, 29.88. C10 H12 N4 requires C, 63.81; H, 6.43; N, 29.77%.

According to the analysis of related databases, 94220-38-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Beecham Group p.l.c.; US4670432; (1987); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1461602-59-4, 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. 1461602-59-4, name is 3-(Methylamino)isonicotinic Acid. A new synthetic method of this compound is introduced below.

3-(Methylamino)isonicotinic acid (4.00 g, 26.3 mmol), 1-hydroxybenzotriazole (10.7 g, 78.9 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (15.1 g, 78.9 mmol) and ammonium chloride (5.63 g, 105 mmol) were dissolved in N,N-dimethylformamide (5 mL). The reaction solution was stirred at 25 C. for 24 hours. The reaction was quenched by adding water (100 mL). The mixture was extracted with isopropanol/chloroform (1:3) (50 mL*2). The organic phases were combined, concentrated under reduced pressure. Methylene chloride/methanol (10:1, 30 mL) was added into the residue and then stirred for 10 minutes, followed by filtration. The filter cake was dried to give 3-(methylamino)isonicotinamide (3.50 g, yellow solid) with a yield of 88%. 1H NMR: (400 MHz, DMSO-d6) delta8.09 (s, 2H), 7.80 (d, J=5.2 Hz, 1H), 7.62-7.61 (m, 1H), 7.52-7.48 (m, 1H), 7.43 (d, J=5.2 Hz, 1H), 2.84 (d, J=5.2 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1461602-59-4, its application will become more common.

Reference:
Patent; GUANGDONG ZHONGSHENG PHARMACEUTICAL CO., LTD; WU, Linyun; CHEN, Xiaoxin; ZHANG, Peng; LIU, Xing; ZHANG, Li; LIU, Zhuowei; CHEN, Shuhui; LONG, Chaofeng; (75 pag.)US2018/148451; (2018); 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. 1211517-76-8, name is 3-Bromo-5-fluoro-4-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C6H5BrFN

Copper cyanide (1.87 g, 0.021 mol) was added at room temperature to a sealed tube containing a solution of 3-bromo-5-fluoro-4-methylpyridine (E; 2.0 g, 0.0105 mol) in dimethylformamide (20 mL). The reaction mixture was heated to 150 C for 16 h. It was then cooled to RT, quenched with 20% aqueous ammonia (30 mL) solution and stirred for 5 min. The reaction mixture was extracted with diethyl ether (2 x 100 mL). The organic layers were washed with water (2 x 50 mL), dried over anhydrous sodium sulphate and concentrated to afford 5-fluoro-4-methylnicotinonitrile. 1H NMR (400 MHz, CDC13) delta 8.62 (s, 1 H), 8.56 (s, 1 H), 2.56 (s, 3 H).

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, 1211517-76-8, 3-Bromo-5-fluoro-4-methylpyridine.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BENNETT, D. Jonathan; CAI, Jaiqiang; CARSWELL, Emma; COOKE, Andrew; HOYT, Scott, B.; LONDON, Clare; MACLEAN, John; RATCLIFFE, Paul; TAYLOR, Jerry Andrew; XIONG, Yusheng; SAMANTA, Swapan Kumar; KULKARNI, Bheemashankar, A.; WO2013/43520; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 713143-67-0, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 713143-67-0 as follows.

In anhydrous THF (5 mL) was dissolved the Step 2 compound (0.9 g, 4.80 mmol), to which was added Li i Pr2NH (1.8 M in THF) (3.0 mL, 4.80 mmol) at -78 C. After stirring for 10 min, n-BuLi (1.6 M in THF) (6.0 mL, 9.61 mmol) and diethylchlorophosphonate (0.96 mL, 4.80 mmol) were slowly added. After stirring for 2 h, the mixture was extracted with ethyl acetate and washed twice with saturated aqueous sodium chloride solution. The organic layer was dried over MgSO4 and filtered. The filtrate was concentrated and purified by silica gel column chromatography (CH2Cl2:CH3OH=20:1) to give the title compound (0.55 g, 1.56 mmol). [777] 1H-NMR (300 MHz, CDCl3) delta 1.29(t, J = 6.9 Hz, 7.2 Hz, 6H), 3.46 (d, J = 21.9 Hz, 2H), 4.09~4.16(m, 4H), 7.06~7.12(m, 1H), 7.24~7.49 (m, 4H), 7.82 (dd, J = 2.4 Hz, 2.4 Hz, 1H), 8.76 (d, J = 2.4 Hz, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,713143-67-0, its application will become more common.

Reference:
Patent; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; LG LIFE SCIENCES LTD.; LEE, Sun Kyung; SONG, Jong Whan; LIM, Dong Chul; CHO, Woo Young; PARK, Chul Min; WO2011/162562; (2011); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem