Category: pyridine-derivatives

Electric Literature of 62774-90-7 ,Some common heterocyclic compound, 62774-90-7, molecular formula is C7H5Cl2NO2, 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) Synthesis of 2,6-dichloro-N-(3-fluorobenzyl)-4-methyl-pyridine-3-carboxylic acid amideTo a solution of 17.4 g (84.4 mmol) of 2,6-dichloro-4-methyl-pyridine-3-carboxylic acid in THF (340 ml) were added 10.6 ml (92.9 mmol) 3-fluorobenzylamine, 32.0 g (84.4 mmol) HATU and 35.0 ml (253.3 mmol) NEt3. The RM was then heated at 70 C for 16. After dilution with EtOAc (350 ml) the mixture was washed with a 4M aq. NH4CI sol., a 1M aq. NaHC03 sol. and brine. The organic layer was dried over MgS04 and concentrated in vacuo. Purification of the residue by CC (hexane/EtOAc 3:2) provided 19.5 g (62.3 mmol, 74%) 2,6-dichloro-N- (3-fluorobenzyl)-4-methyl-pyridine-3-carboxylic acid amide.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,62774-90-7, its application will become more common.

Reference:
Patent; GRUeNENTHAL GMBH; KUeHNERT, Sven; BAHRENBERG, Gregor; KLESS, Achim; SCHROeDER, Wolfgang; LUCAS, Simon; WO2012/52167; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 4930-98-7, 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 4930-98-7, name is 2-Hydrazinylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

A. 5-Amino-1-(2-pyridinyl)-1H-pyrazole-4-carboxylic acid, ethyl ester A solution of 21.83 g of 2-hydrazinopyridine and 38.2 g of ethyl(ethoxymethylene)cyanoacetate dissolved in 150 ml of acetic acid and 50 ml of water was heated on a steam bath for approximately 16 hours. The reaction mixture was allowed to cool to room temperature and placed in a refrigerator whereupon crystals slowly formed. The precipitated solid was collected by filtration and washed with cold 50% aqueous ethanol to provide 23.62 g of 5-amino-1-(2-pyridinyl)-1H-pyrazole-4-carboxylic acid, ethyl ester. Yield 50.9%. MP=89-91 C.

According to the analysis of related databases, 4930-98-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Eli Lilly and Company; US4589905; (1986); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 6000-50-6 ,Some common heterocyclic compound, 6000-50-6, molecular formula is C7H10Cl2N2, 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.

2,3-Dihydro-1H-pyrrolo[3,4-c]pyridine dihydrochloride (CAS-No. 6000-50-6, 214 mg, 1.11 mmol) was added to a suspension of raw 4-nitrophenyl {4-[6-oxo-5-(quinolin-5-yl)-1,4,5,6- tetrahydropyridazin-3-yl]phenyl}carbamate (356 mg, 740 mumol) in dichloromethane (14 mL) and N,N-diisopropylethylamine (640 mul, 3.7 mmol). After stirring at r. t. for 2h the mixture was cooled to -20C and the precipitate was filtered off after standing for 12h and washed with cold dichloromethane. The precipitate was stirred in aqueous sodium hydroxide (20 mL, 1M), filtered, washed with water and dried under reduced pressure to give 175 mg (67% purity, 51% yield) of the title compound containing N-{4-[6-oxo-5-(quinolin-5-yl)-1,6- dihydropyridazin-3-yl] phenyl}-1,3-dihydro-2H-pyrrolo[3,4-c]pyridine-2-carboxamide as minor impurity. (0693) LC-MS (Method 2): Rt = 0.78 min; MS (ESIpos): m/z = 463 [M+H]+ (0694) 1H-NMR (400MHz, DMSO-d6) delta [ppm]: 3.29 (dd, 1H), 3.42 (dd, 1H), 4.72 (dd, 1H), 4.81 (br d, 4H), 7.43 (d, 1H), 7.52 (d, 1H), 7.56 (dd, 1H), 7.60 – 7.65 (m, 2H), 7.68 – 7.76 (m, 3H), 7.97 (d, 1H), 8.50 (d, 1H), 8.58 – 8.64 (m, 3H), 8.92 (dd, 1H), 11.20 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6000-50-6, its application will become more common.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; BOeHNKE, Niels; BERGER, Markus; SOMMER, Anette; HAMMER, Stefanie; FERNANDEZ-MONTALVAN, Ernesto, Amaury; STELTEN-LUDWIG, Beatrix; GUeNTHER, Judith; MAHLERT, Christoph; GREVEN, Simone; SARKER, Abul, Basher; TAIT, Michael; (451 pag.)WO2019/149637; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 55676-22-7, 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. 55676-22-7, name is 3-Acetyl-6-chloropyridine, molecular formula is C7H6ClNO, 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.

Tert-butyl 4-((5-acetylpyridin-2-yl)oxy)piperidine-l-carboxylate (6) Tert-butyl 4- hydroxypiperidine-1-carboxylate (5) (1.4 g, 6.94 mmol) was added to a DMF suspension (10 mL) of 60% sodium hydride (0.25 g, 6.16 mmol) at 0C . The solution was stirred at room temperature for 0.5 h. At 0C, 1-(6-chloropyridin-3-yl)ethan-1-one (4) (0.9 g, 5.78 mmol) was added and the solution was stirred for 1 h. Water was added to the reaction solution, followed by extraction with EtOAc and subsequent sequential washing with water and saline and then the resulting organic layer was dried over Na2SO4. Silica gel column chromatography provided tert-butyl 4-((5-acetylpyridin-2- yl)oxy)piperidine-1-carboxylate (6) as a white solid. MS m/z321 [M+H]+.

According to the analysis of related databases, 55676-22-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ISOCURE BIOSCIENCES INC.; ZHANG, Tinghu; CHE, Jianwei; (96 pag.)WO2018/118793; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 52568-28-2 , The common heterocyclic compound, 52568-28-2, name is 2-(Pyridin-2-yl)propan-2-amine, molecular formula is C8H12N2, 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 round bottom flask was added the acid (5 mmol) and dry CH2Cl2 (20 mL). Thenthe flask was submerged in a brine ice bath, N-methylmorpholine (6 mmol) was addedvia syringe and the solution stirred for 15 min. After that, isobutylchloroformate (5.5mmol) was added dropwise over 20 minutes. After stirring for 6 h at ambienttemperature, the resulting mixture was washed with sat. Na2CO3, and brine, dried overMgSO4, filtered and concentrated under reduced pressure. The residue was purified byflash chromatography to give the desired product

The synthetic route of 52568-28-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liu, Bin; Shi, Bing-Feng; Synlett; vol. 27; 16; (2016); p. 2396 – 2400;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 91182-50-2, Adding some certain compound to certain chemical reactions, such as: 91182-50-2, name is 3-Bromo-2-phenylpyridine,molecular formula is C11H8BrN, 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 91182-50-2.

Molecules 1 (2 mmol, 466 mg) and iridium trichloride trihydrate (1 mmol, 352 mg) were weighed into a round-bottomed flask, evacuated, and bubbling nitrogen, and circulated three times. Under a nitrogen atmosphere, 16 mL of a mixed solution of ethylene glycol ether and water (3: 1, v / v) was injected and dissolved by stirring. After reacting at 110 C for 24 hours, the crude product was cooled to room temperature, and filtered through a sand core funnel to obtain a solid, which was washed three times with deionized water and ethanol. The product is obtained after drying in a vacuum drying box.

According to the analysis of related databases, 91182-50-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Nanjing University of Posts and Telecommunications; Zhang Yin; Wang Jun; Lan Yiping; Zhao Qiang; Liu Shujuan; Huang Wei; (11 pag.)CN110330532; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 73290-22-9, Adding some certain compound to certain chemical reactions, such as: 73290-22-9, name is 2-Bromo-5-iodopyridine,molecular formula is C5H3BrIN, 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 73290-22-9.

Step 1: 2-Bromo-5-trimethylsilanylethynyl-pyridine 2-Bromo-5-iodopyridine (2.5 g, 8.8 mmol) was dissolved under nitrogen in 50 ml THF. Bis-(triphenylphosphine)-palladium(II) dichloride (618 mg, 880 mumol, 0.1 equiv.), ethynyltrimethylsilane (950 mg, 1.34 ml, 9.6 mmol, 1.1 equiv.), triethylamine (1.78 g, 2.44 ml, 17.6 mmol, 3 equiv.) and copper(I) iodide (84 mg, 440 mumol, 0.05 equiv.) were added and the mixture was stirred for 3 hours at 50 C. The reaction mixture was cooled and evaporated to dryness. The crude product was purified by flash chromatography on silica gel, eluting with an ethyl acetate:heptane gradient 0:100 to 15:85. The desired 2-bromo-5-trimethylsilanylethynyl-pyridine (1.95 g, 7.7 mmol, 87% yield) was obtained as a white solid, MS: m/e=254.1/256.1 (M+H+).

According to the analysis of related databases, 73290-22-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Green, Luke; Guba, Wolfgang; Jaeschke, Georg; Jolidon, Synese; Lindemann, Lothar; Ricci, Antonio; Rueher, Daniel; Stadler, Heinz; Vieira, Eric; US2011/251169; (2011); 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. 5470-17-7, name is 3-Bromo-2-chloro-5-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 3-Bromo-2-chloro-5-nitropyridine

Example BPreparation of 3-bromo-2-cyclopropylmethoxy-5-nitro-pyridineTo a solution of sodium hydride (2.21 g, 55.34 mmol) in anhydrous DMF (20ml) was added cyclopropylmethanol (CAS Registry No. 2516-33-8) (12.45 ml, 153.2 mmol) under nitrogen at 0 C and the reaction mixture was stirred at 25 C for 30 minutes. Then 3-bromo-2- chloro-5-nitropyridine (CAS Registry No. 5470-17-7) (7.3 g, 30.74 mmol) was added drop wise at 0 C and stirred for two hours at 25 C. Water (60ml) was added to the reaction mixture and extracted with ethyl acetate (3×100 ml). The combined organic layers were washed with water and brine, dried over Na2S04 and evaporated under reduced pressure to get the crude residue (12 g). The crude was purified by column chromatography (2% ethyl acetate/hexane) to get the desired product (2.06 g, 32%) as light yellow solid and 1.7g of unreacted 3-bromo-2-chloro-5- nitropyridine was recovered. MS (LC/MS): not responding, NMR is in agreement with the structure: 1H-NMR (400 MHz, CDC13): delta 0.41 (m, 2H), 0.65 (m, 2H), 1.32 (m, 1H), 4.34 (d, 2H), 8.60 (d, 1H), 8.96 (d, 1H).

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, 5470-17-7, 3-Bromo-2-chloro-5-nitropyridine.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GRETHER, Uwe; HEBEISEN, Paul; HOFFMANN, Torsten; ROEVER, Stephan; WO2012/49190; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 944401-77-8, 2-Amino-4-fluoropyridine, 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, Application In Synthesis of 2-Amino-4-fluoropyridine, blongs to pyridine-derivatives compound. Application In Synthesis of 2-Amino-4-fluoropyridine

In an aluminium foil-covered flask, Intermediate 51 (62.3 g, 506 mmol) was dissolved in acetonitrile (1500 mL), and NBS (86 g, 481 mmol) was added. The mixturewas stirred at ambient temperature for 2 h. The mixture was concentrated to afford a yellow solid. The crude material was dissolved in EtOAc (1000 mL), washed twice with saturated aqueous sodium bicarbonate solution, then with brine, dried with sodium sulphate, filtered and concentrated in vacuo, to afford a light brown solid (71.2 g). The crude material was crystallized from EtOAc (300 mL) and heptane (300 mL) to give the title compound (34.3 g) as brown crystals. LCMS 191(79Br)/193(81Br) [M+H], RT 0.79 minutes.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,944401-77-8, 2-Amino-4-fluoropyridine, and friends who are interested can also refer to it.

Reference:
Patent; UCB PHARMA S.A.; BENTLEY, Jonathan Mark; BROOKINGS, Daniel Christopher; BROWN, Julien Alistair; CAIN, Thomas Paul; CHOVATIA, Praful Tulshi; FOLEY, Anne Marie; GALLIMORE, Ellen Olivia; GLEAVE, Laura Jane; HEIFETZ, Alexander; HORSLEY, Helen Tracey; HUTCHINGS, Martin Clive; JACKSON, Victoria Elizabeth; JOHNSON, James Andrew; JOHNSTONE, Craig; KROEPLIEN, Boris; LECOMTE, Fabien Claude; LEIGH, Deborah; LOWE, Martin Alexander; MADDEN, James; PORTER, John Robert; QUINCEY, Joanna Rachel; REED, Laura Claire; REUBERSON, James Thomas; RICHARDSON, Anthony John; RICHARDSON, Sarah Emily; SELBY, Matthew Duncan; SHAW, Michael Alan; ZHU, Zhaoning; WO2014/9295; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 16665-38-6, (4-Methoxypyridin-2-yl)methanol, 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, 16665-38-6, blongs to pyridine-derivatives compound. Formula: C7H9NO2

14. 2-Chloromethyl-4-methoxypyridine hydrochloride 15 ml of thionyl chloride are added dropwise to a solution, cooled to -10 C., of 10 g (0.072 mole) of 2-hydroxymethyl-4-methoxypyridine in 30 ml of dry chloroform in the course of 15 minutes. The solution is allowed to come to room temperature and stirring is continued for one and a half hours. After the solvent and the excess thionyl chloride have been stripped off, colorless crystals are obtained, and these are recrystallized from isopropanol [12.1 g (87%), m.p. 149-150 C., decomposition].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,16665-38-6, its application will become more common.

Reference:
Patent; Byk Gulden Lomberg Chemische Fabrik GmbH; US4560693; (1985); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem