Category: pyridine-derivatives

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.58584-86-4, name is Ethyl 2,6-dichloronicotinate, molecular formula is C8H7Cl2NO2, molecular weight is 220.05, as common compound, the synthetic route is as follows.Application In Synthesis of Ethyl 2,6-dichloronicotinate

Step 2: ethyl 6-chloiO-2-ethoxynicotinate; To a solution of ethyl 2,6-dichloronicotinate (5.0 g, 22.72 mmol) in dichloromethane (25 ml_) at 00C was added sodium ethoxide (2.12 g, 29.5 mmol) slowly. The reaction was stirred at 00C for 3 h and then warmed to ambient temperature over 16 h. The reaction was diluted with dichloromethane (20 ml_) and water (20 ml_) and the layers were separated. The aqueous layer was extracted an additional time with dichloromethane (20 ml_). The organic layers were combined, washed with brine (20 ml_), dried over magnesium sulfate, filtered, and concentrated to give the title compound (4.38 g, 84%) as a light yellow solid. 1 H NMR (400 MHz, DMSO-Cf6) delta ppm 1.22 – 1.40 (m, 6 H) 4.27 (q, J=7.03 Hz, 2 H) 4.37 (q, J=7.03 Hz, 2 H) 7.18 (d, J=8.00 Hz, 1 H) 8.15 (d, J=8.00 Hz, 1 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,58584-86-4, Ethyl 2,6-dichloronicotinate, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER INC.; ARHANCET, Graciela Barbieri; CASIMIRO-GARCIA, Agustin; CHEN, Xiangyang; HEPWORTH, David; MEYERS, Marvin Jay; PIOTROWSKI, David Walter; RAHEJA, Raj Kumar; WO2010/116282; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1597-32-6, 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.1597-32-6, name is 2-Amino-6-fluoropyridine, molecular formula is C5H5FN2, molecular weight is 112.11, as common compound, the synthetic route is as follows.

A mixture of 6-fluoropyridin-2-amine (0.5 g, 4.46 mmol) and 2-(methoxymethyl)pyrrolidine (0.617 g, 5.35 mmol) in water (0.2 mL) was heated to 205 C for 0.5 h in a sealed tube in a microwave oven then concentrated in vacuo. The residue was purified by chromatography (silica gel, 10 g, 200 ~ 300 mesh, ethyl acetate : petroleum ether = 1 : 15 ) to afford 6-(2- (methoxymethyl)pyrrolidin-l-yl)pyridin-2-amine (0.68 g, 74 %) as a yellow oil. LC-MS: [M + l]+ =208 ‘ tR = 1.052min.

Statistics shows that 1597-32-6 is playing an increasingly important role. we look forward to future research findings about 2-Amino-6-fluoropyridine.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HERMANN, Johannes Cornelius; KUGLSTATTER, Andreas; LUCAS, Matthew C.; PADILLA, Fernando; WANNER, Jutta; ZHANG, Xiaohu; WO2013/64445; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1211533-83-3, 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 1211533-83-3, name is 5-Bromo-6-methoxypyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 5-bromo-6-methoxypyridin-2-amine (50 mg, 246.2 umol) and 2- methylbenzene-l-sulfonyl chloride (70.4 mg, 369.3 umol, 53.3 uL) in DCM (3.0 mL) was added pyridine (58.4 mg, 738.7 umol, 59.6 uL), the mixture was stirred at 45C for 12 h. The reaction mixture was concentrated under reduced pressure to give a residue. The residue was purified by prep-TLC (Si02) to give N-(5-bromo-6-methoxypyridin-2-yl)-2-methylbenzenesulfonamide (80 mg, 208.2 umol, 84.5% yield). M+H+ = 359.1 (LCMS).

According to the analysis of related databases, 1211533-83-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; QUENTIS THERAPEUTICS, INC.; VACCA, Joseph P.; LI, Dansu; BETTIGOLE, Sarah; (184 pag.)WO2018/222918; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 571189-49-6, 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 571189-49-6, name is 5-(4-Methylpiperazin-1-yl)pyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: The mixture of intermediate 18 (or 24a-h or 27a-g, 0.50mmol), intermediate 19 (or 28, 0.55mmol), Pd(OAc)2 (0.05mmol), X-phos (or Xantphos, 0.15mmol), Cs2CO3 (1.25mmol) and 1,4-dioxane (or 1,2-dimethoxyethane, DME) were refluxed under argon atmosphere for 1h-4h. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography to produce title compounds 20a-d, 25a-h and 29a-g.

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 571189-49-6, 5-(4-Methylpiperazin-1-yl)pyridin-2-amine.

Reference:
Article; Zhang, Hao; Wang, Jin; Zhao, Hong-Yi; Yang, Xue-Yan; Lei, Hao; Xin, Minhang; Cao, Yong-Xiao; Zhang, San-Qi; Bioorganic and Medicinal Chemistry; vol. 26; 12; (2018); p. 3619 – 3633;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 71469-93-7 ,Some common heterocyclic compound, 71469-93-7, molecular formula is C7H8N2O2, 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 At 0 C., in a solution of 4-amino-pyridine-2-carboxylic acid methyl ester (Key Intermediate II) (1.2 g, 7.8 mmol, 2 eq) and diphenyldiazomethane (758 mg, 3.9 mmol, 1 eq) in tetrahydrofurane (40 mL), was bubbled sulfur dioxide until the red color disappeared. The solution was then stirred from 0 C. to room temperature for 3 days. The mixture was filtered and the filtrate was evaporated. The crude residue was purified by flash chromatography using cyclohexane and ethyl acetate (0/100 to 100/0) to afford 4-(diphenyl-methanesulfonylamino)-pyridine-2-carboxylic acid methyl ester as a pale yellow powder (665 mg, 45% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,71469-93-7, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE LTD; EUROPEAN MOLECULAR BIOLOGY LABORATORY (EMBL); SAVIRA PHARMACEUTICALS GMBH; CLASSEN-HOUBEN, Dirk; WOLKERSTORFER, Andrea; SZOLAR, Oliver; SMITH, Mark; SO, Sung-Sau; CUSACK, Stephen; LANGER, Thierry; GIETHLEN, Bruno; MORICE, Christophe; MICHAUT-SIMON, Celine; ZUBIETA, Chloe; US2013/102600; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 60832-72-6, 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. 60832-72-6, name is Oxazolo[4,5-b]pyridin-2(3H)-one, molecular formula is C6H4N2O2, 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: To a solution of 3H-oxazolo[4,5-b]pyridin-2-one (13.6 g, 100 mmol) in acetonitrile (600 mL) and acetic acid (120 mL) was added N-bromosuccinimide (21.4 g, 120 mmol). The mixture was stirred at room temperature for 4 hr and the reaction was quenched with Na2S2O5 solution. After evaporation, the residue was partitioned between ethyl acetate and water. The organic layer was washed with 2N NaOH solution, brine, and dried over Na2SO4. The crude product was purified on a silica gel column to provide 6-bromo-3H-oxazolo[4,5-b]pyridin-2-one (11.5 g, 55% yield).

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 60832-72-6, Oxazolo[4,5-b]pyridin-2(3H)-one.

Reference:
Patent; AGOURON PHARMACEUTICALS, INC.; US2006/46991; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1206968-88-8, (5-Bromo-3-chloropyridin-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, category: pyridine-derivatives, blongs to pyridine-derivatives compound. category: pyridine-derivatives

DMP (45.83g, 102.lOmmoI) was added portion wise to a stirred solution of (5-bromo-3-chloropyridin-2-yl)-methanol (16g, 72.O7mmoI) in DCM (320mL) at 0C and stirred for 16h at RT. The RM was filtered through celite and washed with DCM (3x100mL).The filtrate was washed with Aq.NaHCO3 (200mL), water (200mL), brine(250mL), dried (Na2SO4), filtered, concentrated under reduced pressure to give crude. The crude was purified by CC (0-5% EtOAc in PE) to give 5-bromo-3-chloropicolinaldehyde (lOg, 66%) as light yellow solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1206968-88-8, (5-Bromo-3-chloropyridin-2-yl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; GRUeNENTHAL GMBH; SCHUNK, Stefan; REICH, Melanie; JAKOB, Florian; DAMANN, Nils; HAURAND, Michael; KLESS, Achim; ROGERS, Marc; SUTTON, Kathy; WO2015/158427; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1446507-38-5, 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. 1446507-38-5, name is 6-(6-(Trifluoromethyl)pyridin-2-yl)-1,3,5-triazine-2,4(1H,3H)-dione, molecular formula is C9H5F3N4O2, 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.

Step 3: Preparation of 2,4-dichloro-6-(6-trfluomethyl-pyridin-2-yl)-1,3,5-triazine. To a solution of 6-(6-trifluomethyl-pyridin-2-yl)-1 ,3 ,5-triazine-2,4(1 H,3H)-dione (3.37 g, 0.013 mol) in POC13 (48 mL) was added PC15 (23 g, 0.1 mol). The mixture was stirred at 100C for 2 hr and then concentrated. The residue was dissolved inEtOAc and then washed with Sat. aq. NaHCO3. The organic layer was dried over anhydrous Na2504 and thenconcentrated to give the desired product.?H NMR (400 MHz, CDC13): 8.76 (d, J= 7.9 Hz, 1H), 8.19 (t, J 7.9 Hz, 1H), 7.97 (d, J 7.8 Hz, 1H).LC-MS: m/z 294.9 (M+H).

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 1446507-38-5, 6-(6-(Trifluoromethyl)pyridin-2-yl)-1,3,5-triazine-2,4(1H,3H)-dione.

Reference:
Patent; AGIOS PHARMACEUTICALS, INC.; KONTEATIS, Zenon D.; POPOVICI-MULLER, Janeta; TRAVINS, Jeremy M.; ZAHLER, Robert; CAI, Zhenwei; ZHOU, Ding; WO2015/3640; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 124236-37-9, Adding some certain compound to certain chemical reactions, such as: 124236-37-9, name is Methyl 5-(trifluoromethyl)picolinate,molecular formula is C8H6F3NO2, 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 124236-37-9.

b) 1 -Oxy-5-trifluoromethyl-pyridine-2-carboxylic acid methyl ester A mixture of 5-(trifluoromethyl)-pyridine-2-carboxylic acid methyl ester (2.7 g, 13 mmol) and m-CPBA (CAN 937-14-4, 6.7 g, 39 mmol) in dry methylene chloride (30 mL) was stilTed under reflux conditions overnight. Removal of the solvent in vacuo and purification of the obtained residue by column chromatography (silica gel, 15 g, 20% ethyl acetate in petroleum ether) provided the title compound (2.2 g, 76%) as light-yellow solid; MS (El):mle = 222.1 [MHi.

According to the analysis of related databases, 124236-37-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; FREI, Beat; GOBBI, Luca; GRETHER, Uwe; KIMBARA, Atsushi; NETTEKOVEN, Matthias; ROEVER, Stephan; ROGERS-EVANS, Mark; SCHULZ-GASCH, Tanja; WO2014/86705; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1137-68-4, 2-(2-Pyridyl)benzimidazole, 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, 1137-68-4, blongs to pyridine-derivatives compound. Computed Properties of C12H9N3

The 2-(pyridin-2-yl)-1H-benzo[d]imidazole (2.0g, 0.0102 mol)was dissolved in 30 ml of dry DMF and stirred with potassiumcarbonate (1.4g, 0.0102 mol) at room temperature for 1 h and 2-(Bromomethyl naphthalene) (2.2. g, 0.0102 mol) was dissolved in20 ml of THF then added dropwise using dropping funnel proceedthe reaction for further 12 h. The proceeding of product waschecked by thin layer chromatography. After the completion ofreaction solvent was rescued under vacuum, the resulting solidswere treated with 30 ml of HCl washed using ethyl acetate anddistilled water. The separated organic layer is filtered over sodiumsulphate then the compound was purified under column chromatographytechnique (Hexane: ethyl acetate-10:90) to obtain whitesolid as the product. Yield 78%, 1H NMR (500 MHz, CDCl3) d 8.51 (d,J 4.3 Hz, 1H), 8.37 (d, J 8.0 Hz, 1H), 7.85e7.52 (m, 5H), 7.45 (s,1H), 7.33e7.05 (m, 7H), 6.25 (s, 2H). 13C NMR (126 MHz, CDCl3)d 150.52, 150.01, 148.68, 142.72, 136.92, 134.97, 133.29, 132.71,128.45, 127.81, 127.61, 126.22, 125.88, 125.40, 124.89, 124.75, 123.92,123.69, 122.93, 120.16, 49.20. HRMS (ESI): calcd. For [MH]C23H17N3 336.1495 found 336.1497. The data is given in supp. data eFig. S4aec.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1137-68-4, its application will become more common.

Reference:
Article; Balamurugan, Selvaraj; Ganesan, Shanmugam; Electrochimica Acta; vol. 329; (2020);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem