Pyridine-derivatives

Related Products of 52311-50-9, Adding some certain compound to certain chemical reactions, such as: 52311-50-9, name is 2-Chloro-4-ethoxypyridine,molecular formula is C7H8ClNO, 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 52311-50-9.

Solid 2-chloro-4-ethoxypyridine (100 g 0.63 mol) was added to H2SO4(500 mL) slowly. Then 1-bromopyrrolidine-2 5-dione (124.2 g 0.70 mol) was added into above mixture at rt. The mixture was stirred at 80 for 3 h. TLC (PE/EA 101 Rf 0.5) showed the reaction was finished. The reaction mixture was poured into ice-water (2 L) and extracted with EA (1 L x 3) . The organic layer was washed with saturated Na2CO3solution (1 L x 2) dried over Na2SO4and concentrated. The residue was purified on silica column chromatography (PE/EA 601-301) . All fractions found to contain product by TLC (PE/EA 101 Rf 0.5) were combined and concentrated to yield 5-bromo-2-chloro-4-ethoxypyridine (60.9 g 0.26 mol 40yield) 1HNMR(400 MHz CD3OD) delta 8.31 (s 1H) 7.14 (s 1H) 4.32-4.10 (m 2H) 1.58-1.35 (m 3H) ES-LCMS m/z 237 (M+2)

According to the analysis of related databases, 52311-50-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; GLAXOSMITHKLINE (CHINA) R & D COMPANY LIMITED; CHEUNG, Mui; DEMARTINO, Michael P.; EIDAM, Hilary Schenck; GUAN, Huiping Amy; QIN, Donghui; WU, Chengde; GONG, Zhen; YANG, Haiying; YU, Haiyu; ZHANG, Zhiliu; (391 pag.)WO2016/37578; (2016); 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. 685517-67-3, name is 2,6-Difluoro-3-iodopyridine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C5H2F2IN

n-Butyllithium (1.66mL, 4.15mmol, 2.5mol/L in hexane) was added dropwise to a solution of diisopropylamine (1.30mL, 4.15mmol) in THF (2mL) at -78C. After 25min 2,6-difluoro-3-iodopyridine (1.00g, 4.15mmol) in THF (5mL) was added dropwise into this mixture by cannula. After 12h at -78C, H2O (0.2mL, 11mmol) in THF (2mL) was added and the mixture was warmed to room temperature during 1h. The mixture was washed with 10% aqueous Na2SO3 (5mL) and extracted with ethyl acetate (3×50mL). The organic extracts were dried (MgSO4) and concentrated in vacuo. Crystallization from hexane afforded the product as colorless crystals (740mg, 74%). 1H NMR (400MHz, CDCl3): delta 7.22 (t, 2H,J=1.2). 13C NMR (100MHz, CDCl3): 161.1 (dd, J=250, 16, 2C), 115.6 (dd, J=24, 10, 2C), 110.3. 19F NMR (376MHz, CDCl3): delta -68.1. GC-MS m/z calcd. for C5H2F2IN [M+]: 241, found: 241. MP: 78-80C.

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, 685517-67-3, 2,6-Difluoro-3-iodopyridine.

Reference:
Article; Jin, Xin; Cramer, Jacob R.; Chen, Qi-Wei; Liang, Hai-Lin; Shang, Jian; Shao, Xiang; Chen, Wei; Xu, Guo-Qin; Gothelf, Kurt V.; Wu, Kai; Chinese Chemical Letters; vol. 28; 3; (2017); p. 525 – 530;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1227573-02-5 ,Some common heterocyclic compound, 1227573-02-5, molecular formula is C6H3BrFNO, 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 3: 2-Chloro-4-(5-fluoro-4-formyl-pyridin-3-yl)-benzonitrile (15c)To the solution of 2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (264 mg, 1.00 mmol), 3-bromo-5-fluoroisonicotinaldehyde (204 mg, 1.00 mmol) and PdCI2(PPh3)2 (56 mg, 0.08 mmol) in DMF (3 mL) was added 2M Na2C03 solution (1.50 ml, 3.00 mmol) under nitrogen atmosphere. The mixture was stirred and heated at 100C for 4hrs. After letting cool to room temperature, solvent was removed in vacuo. The resulting residue was dissolved in DCM and saturated NH4CI solution. After extraction and separation, the combined extracts were concentrated and purified by SNAPI Og (10%MeOH/DCM 0- 15%gradient) to give 2-chloro-4-(5-fluoro-4-formylpyridin-3-yl)benzonitrile (47 mg, 18%) as a white solid.; ESI-MS m/z: 293 [M+MeOH+1]+, Retention time 1.15min. -NMR (CDCI3, 400 MHz) delta 7.33 (dd, J= 8.0, 1.6 Hz, 1 H), 7.50 (d, J= 1.6 Hz, 1 H), 7.78 (d, J= 8.0 Hz, 1 H), 8.49 (s, 1 H), 8.78 (d, J= 1.2 Hz, 1H), 10.27 (s, 1H)

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. 1227573-02-5, 3-Bromo-5-fluoroisonicotinaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; ALLAN, Martin; CHAMOIN, Sylvie; HU, Qi-Ying; IMASE, Hidetomo; PAPILLON, Julien; WO2011/61168; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 87674-21-3, Adding some certain compound to certain chemical reactions, such as: 87674-21-3, name is 1-(3-Fluoropyridin-4-yl)ethanone,molecular formula is C7H6FNO, 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 87674-21-3.

[0378] 3-Fluoro-l-(2-bromo-4-pyridinyl)ethanone Hydrobromide (169). l-(3- Fluoro-4-pyridinyl)ethanone (168) (880 mg, 6.33 mmol) was dissolved in glacial acetic acid (20 mL) and treated with bromine (0.36 mL, 7.0 mmol) followed by HBr/AcOH (30% w/v, 1.4 mL, 7.0 mmol) at 5-10 0C. The reaction mixture was stirred at 20 0C for 3 h, it was then diluted with Et2O (100 mL) and the precipitate was filtered off, washed with Et2O and dried under high vacuum to afford the crude bromoketone 169 (1.65 g) as a pale yellow solid that was used without further purification.

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. 87674-21-3, 1-(3-Fluoropyridin-4-yl)ethanone, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE BOARD OF TRUSTEES OF THE LELAND STANFORD JUNIOR UNIVERSITY; AUCKLAND UNISERVICES LIMITED; WO2009/114552; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 60186-15-4, 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. 60186-15-4, name is 2,4-Difluoro-5-nitropyridine. A new synthetic method of this compound is introduced below.

In a 250 mL round-bottomed flask vial was 2,4-difluoro-5-nitropyridine (1.035 g, 6.47 mmol) in tetrahydrofuran (30 mL) to give a tan solution. After cooling to -40 C, 1 -allylpiperazine (0.905 mL, 6.47 mmol) was added, followed by Et3N (1.802 mL, 12.93 mmol). The cloudy tan mixture was stirred at -40 C – -10C for 3 h. TLC (1/1 EtOAc/hexane) showed one major more polar yellow spot. The mixture was concentrated, and the residue was purified by FCC up to 80% EtOAc/hexane to afford the desired product (1.4347 g, 83%) as a yellow solid: 1H NMR (0112) (400 MHz, Chloroform-d) delta 8.58 (s, 1H), 6.41 (s, 1H), 5.97 – 5.77 (m, 1H), 5.31 – 5.1 (m, 2H), 3.33 – 3.23 (m, 4H), 3.09 (dt, J = 6.7, 1.3 Hz, 2H), 2.68 – 2.58 (m, 4H); 19F NMR (376 MHz, Chloroform-d) delta -62.07.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,60186-15-4, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LUO, Guanglin; SIVAPRAKASAM, Prasanna; DUBOWCHIK, Gene M.; MACOR, John E.; (45 pag.)WO2018/98413; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 863878-22-2, 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. 863878-22-2, name is 6-Chloro-4-methyl-3-nitropyridin-2-amine. A new synthetic method of this compound is introduced below.

Step 1 : (‘/?/)-(1-(6-Amino-4-methyl-5-nitropyridin-2-yl)piperidin-3-yl)(pyrrolidin-1 – yl)methanone (‘/?/)-(1 -(6-Amino-4-methyl-5-nitropyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone was prepared using a method analogous to the one used for Intermediate 2, Step 1 but using 6-chloro-4-methyl-3-nitropyridin-2-amine and (7?,)-piperidin-3-yl(pyrrolidin-1 – yl)methanone as starting materials. The reaction mixture was run at 70C for 1 h. MS (ES+APCI) (M+H) 333.9; LCMS retention time 4.322 min (Method Z).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,863878-22-2, 6-Chloro-4-methyl-3-nitropyridin-2-amine, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER INC.; AHN, Kay; BOEHM, Markus; CABRAL, Shawn; CARPINO, Philip A.; FUTATSUGI, Kentaro; HEPWORTH, David; KUNG, Daniel W.; ORR, Suvi; WANG, Jian; WO2013/150416; (2013); 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. 956010-87-0, name is 3-(Trifluoromethyl)-1H-pyrazolo[3,4-b]pyridine. A new synthetic method of this compound is introduced below., Safety of 3-(Trifluoromethyl)-1H-pyrazolo[3,4-b]pyridine

To compound 12 (200 mg, 1.07 mmol) and N,N-dimethylhydrazinecarbothioamide (153 mg, 1.28 mmol) was added a 1N aqueous sodium hydroxide solution (4.0mL), and the mixture was heated in a microwave oven to 150 C for 10 min. The precipitate was collected by suction filtration and washed with water to yield 106 mg (40 %) of the title compound as a tan solid. 1H NMR (400 MHz, DMSO-d6): delta 3.18 (s, 6H), 7.36 (dd, J=8.0, 4.4Hz, 1H), 8.59 (dd, J=8.0, 1.5Hz, 1H), 8.63 (dd, J=4.4, 1.5Hz, 1H), 14.08 (br s, 1H). 13C NMR (125 MHz, DMSO-d6): delta 41.1, 111.4, 118.3, 130.8, 136.3, 150.0, 151.2, 152.4, 170.4. HRMS m/z calcd for C10H10N6S: 246.0688; found: 246.0680.

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, 956010-87-0, 3-(Trifluoromethyl)-1H-pyrazolo[3,4-b]pyridine.

Reference:
Article; Schirok, Hartmut; Griebenow, Nils; Fuerstner, Chantal; Dilmac, Alicia M.; Tetrahedron; vol. 71; 34; (2015); p. 5597 – 5601;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 131747-62-1, 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.131747-62-1, name is 3-(Trifluoromethyl)pyridine-2-carboxaldehyde, molecular formula is C7H4F3NO, molecular weight is 175.108, as common compound, the synthetic route is as follows.

Intermediate 1: (S)-(4-(Trifluoromethyl)phenyl)(3-(trifluoromethyl)pyridin- 2-yl)methanamine hydrochlorideStep 1. (S^)-2-Methyl-N-((3-(trifluoromethyl)pyridin-2-yl)methylene)- propane-2-sulfinamideTo a solution of 3-(trifluoromethyl)picolinaldehyde (Frontier Scientific, 9.80 g, 56.0 mmol) and DCM (50 mL) was added (5)-2-methylpropane-2- sulfinamide (AK Scientific, 10.3 g, 85.0 mmol) and copper(II) sulfate (35.3 g, 221 mmol). After 1.5 h at rt, the reaction was filtered through a pad of Celite brand filter agent and rinsed with DCM. The filtrate was concentrated in vacuo to give a dark green oil. The oil thus obtained was loaded onto a silica gel column and eluted with 30% EtOAc in hexanes to give (S,E)-2-methyl-N-((3-(trifluoro- methyl)pyridin-2-yl)methylene)propane-2-sulfinamide, as a golden oil. 1H NMR (delta ppm, CDCI3, 300 MHz): 9.02 (d, J = 4.3 Hz, 1H), 8.70 (d, J = 1.3 Hz, 1H), 8.38 (d, J = 7.7 Hz, 1H), 7.79 (dd, J = 7.9 & 4.8 Hz, 1H), 1.18 (s, 9H). MS (ESI pos. ion) m/z: 279.1 (M+H).

The chemical industry reduces the impact on the environment during synthesis 131747-62-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; AMGEN INC.; BISWAS, Kaustav; BROWN, James; CHEN, Jian, J.; GORE, Vijay, Keshav; HARRIED, Scott; HORNE, Daniel, B.; KALLER, Matthew, R.; LIU, Qingyian; MA, Vu, Van; MONENSCHEIN, Holger; NGUYEN, Thomas, T.; YUAN, Chester, Chenguang; ZHONG, Wenge; ST. JEAN, David, J., Jr.; WO2012/177893; (2012); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 62002-31-7, 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. 62002-31-7, name is 4,5,6,7-Tetrahydro-3H-imidazo[4,5-c]pyridine dihydrochloride, molecular formula is C6H11Cl2N3, 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.

1-Hydroxy-7-azabenzotriazole (0.32 g, 2.4 mmol) was added to a solution of phenylpropiolic acid (0.34 g, 2.4 mmol) in dichloromethane (30 mL). The solution was cooled to 0 C. EDC (0.45 g, 2.4 mmol) was added. The reaction mixture was stirred at 0 C. for 20 min. 4,5,6,7-Tetrahydroimidazo[4,5-c]pyridine dihycrochloride (0.50 g, 2.3 mmol) was added. Ethyldiisopropylamine (0.40 mL, 2.3 mmol) was added. The reaction mixture was stirred for 16 h at room temperature. It was diluted with ethyl acetate (100 mL) and washed with 10% aqueous sodium hydrogensulfate solution (100 mL). The aqueous phase was extracted with ethyl acetate (3*60 mL): It was added a 1 N sodium hydroxide solution until pH 12 was obtained. It was extracted with ethyl acetate (3*90 mL). These extracts were combined and dried over magnesium sulfate. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (40 g), using dichloromethane/methanol/25% aqueous ammonia (100:10:1) as eluent, to give 50 mg of the title compound. 1H NMR (CDCl3, 2 rotamers): delta2.75 and 2.85 (both t, together 2H); 4.03 and 4.15 (both t, together 2H); 4.75 and 4.92 (both s, together 1H); 7.10-7.70 (m, 6H).

According to the analysis of related databases, 62002-31-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Novo Nordisk A/S; US6908926; (2005); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem