Category: pyridine-derivatives

Application of 65515-28-8, 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 65515-28-8, name is Methyl 2,6-dichloronicotinate. This compound has unique chemical properties. The synthetic route is as follows.

A 2.5 M hexane solution of BuLi (32.6 mL, 82 mmol) was added dropwise to a solution of diisopropylamine (12.11 mL, 85 mmol) in THF (100 mL) at -78 0C. The mixture was stirred at 0 0C for 15 min and cooled to -78 0C. Acetonitrile (4.26 mL, 82 mmol) was added dropwise. The solution gradually turned to milky white. After 1 h at -78 0C, methyl 2,6-dichloronicotinate (7.00 g, 34.0 mmol) in THF (25 mL) was added dropwise. The flask was rinsed with THF (5 mL) and added. After 1 h at -78 0C, the mixture was quenched with brine (100 mL), acidified to pH~l and extracted with EtOAc (3×100 mL). The combined extracts were washed with brine (50 mL), dried (MgSO4) and concentrated. Silica gel chromatography, eluting with 0- 5% methanol in CH2Cl2, gave the desired product as yellow solid (4.6374 g, 64% yield). MS (ES+) m/z: 215 (M+H); LC retention time: 2.45 min (analytical HPLC Method A).

According to the analysis of related databases, 65515-28-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2009/100171; (2009); 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.760207-83-8, name is 3-Bromo-5-chloropicolinonitrile, molecular formula is C6H2BrClN2, molecular weight is 217.45, as common compound, the synthetic route is as follows.Safety of 3-Bromo-5-chloropicolinonitrile

Synthesis of 5-chloro-3-vinylpicolinic acid A sealable vial was charged with 3-bromo-5-chloropicolinonitrile (700 mg, 3.22 mmol) and dichlorobis(triphenyl-phosphine)palladium(II) (271 mg, 0.386 mmol). The vial was evacuated and backfilled with nitrogen. 1,4-dioxane (5 mL) was added, followed by tri-n-butyl(vinyl)tin (1.225 mL, 3.86 mmol). The reaction mixture was heated to 100 C. The reaction mixture was diluted with water and EtOAc. The solvent was removed under reduced pressure. The residue was dissolved in EtOH (3 mL) and NaOH (1M, 6 mL). The cloudy solution was heated to 100 C. for 15 min. The reaction mixture was cooled to RT, the aqueous phase was separated and neutralized with 1 M HCl. The aqueous phase was back-extracted with EtOAc. The organic phase was separated and dried over MgSO4. The solvent was removed under reduced pressure to obtain 5-chloro-3-vinylpicolinic acid (120 mg, 0.654 mmol, 20.30% yield) as a yellow solid. 1H NMR (300 MHz, DMSO-d6) delta ppm 5.56 (d, J=11.11 Hz, 1H) 6.07 (d, J=17.54 Hz, 1H) 7.12 (dd, J=17.54, 11.11 Hz, 1H) 8.33 (d, J=2.19 Hz, 1H) 8.58 (d, J=2.19 Hz, 1H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,760207-83-8, 3-Bromo-5-chloropicolinonitrile, and friends who are interested can also refer to it.

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 13958-99-1, 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. 13958-99-1, name is 3-Bromoisonicotinamide. A new synthetic method of this compound is introduced below.

3- Bromo-4-cyanopyridine (34). 3-Bromopyridine-4-carboxamide98 (687 mg, 3.4 mmol) was added to phosphorus oxychloride (5.0 ml_) at 0C. The mixture was then stirred at reflux for 2 h. The mixture was cooled, poured onto ice (100 g) with stirring and was neutralised with aqueous sodium hydroxide (5 M, 60 ml_). The mixture was extracted with diethyl ether (2 chi 50 mL). The combined organic layers were washed with saturated aqueous sodium hydrogen carbonate, treated with charcoal and filtered. The solvent was evaporated. The solid was recrystallised from petroleum ether to give 34 (292 mg, 42%) as an off-white powder: mp 79-81 C (lit.99 mp 96.6-98.2C); 1H NMR (CDCI3) delta 7.53 (1 H, d, J = 4.9 Hz, 5-H), 8.69 (1 H, d, J = 4.9 Hz, 6-H), 8.92 (1 H, s, 2- H); 13C NMR (CDCI3) (HSQC / HMBC) delta 1 14.79 (C?N), 122.14 (4-C), 124.17 (3-C), 126.75 (5-C), 148.76 (6-C), 152.69 (2-C); MS (ESI) m/z 182.9552 (M + H) (C6H4N279Br requires 182.9541).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13958-99-1, its application will become more common.

Reference:
Patent; UNIVERSITY OF BATH; THREADGILL, Michael David; LLOYD, Matthew David; THOMPSON, Andrew Spencer; NATHUBHAI, Amit; WOOD, Pauline Joy; PAINE, Helen Angharad; KUMPAN, Ekaterina; SUNDERLAND, Peter Thomas; CHUE YEN WOON, Esther; WO2014/87165; (2014); 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. 63071-10-3, name is (4-Chloropyridin-2-yl)methanol, molecular formula is C6H6ClNO, 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: C6H6ClNO

Intermediate 34, 1-(3-bromo-4-{[(4-chloro-2-pyridinyl)methyl]oxy}phenyl)ethanone To a stirred solution of (4-chloro-2-pyridinyl)methanol (Commercial eg Aldrich) (0.2 g) in THF (5 ml) were added 1-(3-bromo-4-hydroxyphenyl)ethanone (0.3 g) and triphenylphosphine (0.547 g). This was stirred for 10 min before cooling and adding slowly DEAD (0.363 g). This was stirred for 16 h. The reaction mixture was partitioned between water and ethyl acetate. The aqueous was reextracted with ethyl acetate and the combined organics were washed with brine, dried over sodium sulfate and concentrated in vacuo. This was purified through silica eluting with 0-35% ethyl acetate in hexane to give the title compound, 0.30 g Mass Spec: [MH]+=340, 342

With the rapid development of chemical substances, we look forward to future research findings about 63071-10-3.

Reference:
Patent; GLAXO GROUP LIMITED; US2012/232061; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 57266-69-0 ,Some common heterocyclic compound, 57266-69-0, molecular formula is C6H4ClNO2, 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.

3-Chloro-2-picolinic acid (47.3 mg, 0.3 mmol), styrene (33 muL, 0.3 mmol), tert-butyl hypochlorite (68 muL, 0.6 mmol) was weighed into a 25 mL Schlenk reaction flask.Then THF (1 mL) was added and placed in a 25 C oil bath for 6 h. After the reaction,The solvent was removed under reduced pressure, using petroleum ether / ethyl acetate as eluent,The yield of the product was 63%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,57266-69-0, its application will become more common.

Reference:
Patent; Dalian University of Technology; Feng Xiujuan; Zhang Xitao; Bao Ming; Yu Xiaoqiang; Zhang Sheng; (24 pag.)CN110105270; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1017793-20-2 , The common heterocyclic compound, 1017793-20-2, name is 2,5-Difluoro-4-iodopyridine, molecular formula is C5H2F2IN, 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 Example 5A (100 mg, 0.234 mmol) and 2,5-difluoro-4-iodopyridine (200 mg, 0.830 mmol) in 3.5 mL of 1 ,2-dimethoxyethane was added 1.5 mL saturated sodium bicarbonate solution and the mixture was degassed with nitrogen. 1 , 1 ‘-Bis(diphenylphosphino)ferrocene- palladium(II)dichloride dichloromethane complex (33.9 mg, 0.041 mmol) was added and the mixture was heated at 100C for 2 hours. The mixture was cooled to room temperature, diluted with ethyl acetate and filtered through diatomaceous earth. The combined organic layers were washed with water and brine (25 mL each) and dried over sodium sulfate. Filtration, concentration and purification by column chromatography (silica gel, 50% ethyl acetate-hexane) afforded the title compound. LCMS: 415.4 (M+H)+.

The synthetic route of 1017793-20-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBVIE INC.; ABBVIE PHARMACEUTICAL TRADING (SHANGHAI) CO., LTD.; TONG, Yunsong; BRUNCKO, Milan; CLARK, Richard F.; CURTIN, Michael L.; FLORJANCIC, Alan S.; FREY, Robin R.; GONG, Jianchun; HANSEN, Todd M.; JI, Zhiqin; LAI, Chunqiu; MASTRACCHIO, Anthony; MICHAELIDES, Michael; MIYASHIRO, Juliem; RISI, Roberto M.; SONG, Xiaohong; TAO, Zhi-fu; WOODS, Keith W.; ZHU, Guidong; PENNING, Thomas; SOUERS, Andrew; GOSWAMI, Rajeev; IQUTURI, Omprakash Reddy; DABBEERU, Madhu Babu; WO2014/139328; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 769-28-8, 4,6-Dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile, 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, 769-28-8, blongs to pyridine-derivatives compound. Application In Synthesis of 4,6-Dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

To the suspension of 3-cyano-4,6,-dimethyl-2-pyridone (3 g, 0.02 mol) and powdered NaOH (0.80 g, 0.02 mol) in dry DMF (10 ml) stirred at r.t. for 15 min was added 1,3-dibromopropane (2.02 g, 0.01 mol) slowly with constant stirring [41]. The reaction mixture was stirred at room temperature for 12 h. Completion of reaction was confirmed via TLC. There were 3 spots visualized on TLC indicating the formation of region isomers. DMF was removed under reduced pressure using rotavapour and the product was treated with 1:1 CHCl3:H2O system (300 ml). The organic layer was collected and the aqueous layer was washed three times with 300 ml of CHCl3 (100 ml each). The organic layers were combined and washed with water (100 ml) and dried over anhydrous Na2SO4. Column chromatography was done for separation of regioisomers. The first fraction collected at 20% ethyl acetate:hexane was characterized as title compound. This was crystallized with 5% ethyl acetate:hexane and ethyl acetate solution, respectively.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,769-28-8, its application will become more common.

Reference:
Article; Tewari, Ashish Kumar; Singh, Ved Prakash; Dubey, Rashmi; Puerta, Carmen; Valerga, Pedro; Verma, Rajnikant; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; vol. 79; 5; (2011); p. 1267 – 1275;,
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. 19230-57-0, name is 2-Bromo-3-methylpyridine 1-oxide, 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. COA of Formula: C6H6BrNO

To a stirred solution of 2-bromo-3-methyl pyridine-1-oxide (25g) and pyridine (42g) in acetonitrile (250mL) at about 70C, was added a solution of trifluoromethanesulfonic anhydride (55g) in acetonitrile (5OmL). The reaction mixture was stirred for about lh atabout the same temperature. The mixture was cooled to about 10C to about 15C and ethanolamine (80.52g) was added to it. The reaction mixture was stirred for about 3h at about room temperature and water and ethyl acetate were added to it. The two layers were separated and the organic layer was washed with saturated brine solution, dried and concentrated under reduced pressure at about 40C. The residue was purified by columnchromatography (15-20% ethyl acetate in hexane). Yield: 4g (16%)?H NIVIR (300IVIHz, CDC13): oe 7.26-7.24 (d,J8.lOHz,1H), 6.42-6.39 (d,J8.4Hz,1H), 4.28 (brs,2H), 2.22 (s,3H)?3CNMR(400MHz, CDC13): 156.52, 141.56, 140.50, 122.99, 107.26, 20.58 IR: 3364, 3199, 2913, 1635, 1601, 1373, 1058, 819 cm4-Amino-2-bromo-3-methyl pyridine (3g) was obtained which was eluted at 25-30% ethyl acetate in hexane.?H NIVIR (300IVIHz, CDC13): oe 7.82-7.80 (d,J5.4Hz,1H), 6.48-6.46 (d,J 5.4Hz,1H), 4.35 (brs,2H), 2.21 (s,3H)?3CNMR(400MHz, CDC13): 152.70, 146.94, 145.05, 116.88, 109.25, 15.73

With the rapid development of chemical substances, we look forward to future research findings about 19230-57-0.

Reference:
Patent; GLENMARK PHARMACEUTICALS LIMITED; BHIRUD, Shekhar Bhaskar; KADAM, Suresh Mahadev; KANSAGRA, Bipin Parsottam; BHADANE, Shailendra Nilkanth; KALE, Shrikrishna Kantilal; PATIL, Ulhas Digambar; (57 pag.)WO2017/56031; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 909720-21-4, 2,3-Dibromo-6-methoxypyridine, 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, SDS of cas: 909720-21-4, blongs to pyridine-derivatives compound. SDS of cas: 909720-21-4

1,4-Dioxane (450 mL) and water (150 mL) were added to a mixture of 2,3- dibromo-6-methoxypyridine (12 g, 45 mmol), C2 (31.8 g, 135 mmol), di(l -adamantyl)- ?- butylphosphine (cataCXium A; 3.22 g, 8.98 mmol), palladium(ll) acetate (3.03 g, 13.5 mmol), and cesium carbonate (87.9 g, 270 mmol), and the reaction vessel was evacuated and charged with nitrogen. This evacuation cycle was repeated twice, and the reaction mixture was then stirred at reflux for 20 hours. After the reaction mixture had been partitioned between ethyl acetate (300 mL) and saturated aqueous sodium chloride solution (200 mL), the aqueous layer was extracted with ethyl acetate (2 x 200 mL); the combined organic layers were washed with saturated aqueous sodium chloride solution (200 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was treated with triethylamine (3 mL), dissolved in dichloromethane and treated with silica gel; this mixture was concentrated to dryness and used for silica gel chromatography (Gradient: 0% to 6% ethyl acetate in petroleum ether) to afford the product as a brown oil. Yield: 10 g, 27 mmol, 60%. LCMS m/z 388.0 [M+Na+]. 1H NMR (400 MHz, CDCI3) delta 7.39 (d, J=8.3 Hz, 1H), 6.52 (d, J=8.3 Hz, 1H), 4.63 (dd, J=4.0, 2.8 Hz, 1H), 4.58 (dd, J=4.0, 2.8 Hz, 1H), 4.19-4.1 1 (m, 1H), 3.94-3.71 (m, 4H), 3.89 (s, 3H), 3.58-3.42 (m, 3H), 3.05 (t, J=7.2 Hz, 2H), 2.89 (t, J=7.2 Hz, 2H), 1.86-1.74 (m, 2H), 1.74-1.64 (m, 2H), 1.62-1.44 (m, 8H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,909720-21-4, 2,3-Dibromo-6-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER INC.; CHAPPIE, Thomas Allen; HENDERSON, Jaclyn Louise; YOUNG, Joseph Michael; WAGER, Travis T.; KORMOS, Bethany Lyn; PATEL, Nandini Chaturbhai; SCIABOLA, Simone; TUTTLE, Jamison Bryce; VERHOEST, Patrick Robert; TUCKER, Joseph Walter; (181 pag.)WO2017/122116; (2017); 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. 174610-12-9, name is 1H-Pyrrolo[2,3-c]pyridin-5-amine, the common compound, a new synthetic route is introduced below. Product Details of 174610-12-9

General procedure: To a solution of the corresponding amine (4 or 5, 1.2 equiv), dihalo-substituted benzoic acid (2c, 2d, 2e or 2f, 1.0 equiv), and 1-hydroxybenzotriazole hydrate (HOBt, 1.2 equiv) in DMF (8.0-10.0mL/mmol; extra dry over molecular sieves, 99.8%, Acros) were added EDC-HCl (1.2 eqiv) and DIPEA (2.5 equiv). The mixture was stirred at room temperature until completed conversion (TLC control: CH2Cl2/MeOH 9/1 v/v). Then, the solvent was removed in vacuo and the residue washed with water (20mL/mmol) and dried at 70C. The crude product was purified by column chromatography on silica gel (eluent: CH2Cl2/MeOH 9/1 v/v) following by reversed phase HPLC (for purification methods, see Supporting Information, TableS2) and/or recrystallization as described below.

The synthetic route of 174610-12-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tzvetkov, Nikolay T.; Stammler, Hans-Georg; Hristova, Silvia; Atanasov, Atanas G.; Antonov, Liudmil; European Journal of Medicinal Chemistry; vol. 162; (2019); p. 793 – 809;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem