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.1214328-96-7, name is Methyl 3-bromo-6-chloropicolinate, molecular formula is C7H5BrClNO2, molecular weight is 250.48, as common compound, the synthetic route is as follows.Formula: C7H5BrClNO2

B) methyl 6-chloro-3-((E)-2-ethoxyvinyl)pyridine-2-carboxylate To a mixture of methyl 3-bromo-6-chloropyridine-2-carboxylate (2.00 g) in acetonitrile (30 mL) and water (20 mL) were added 2-((E)-2-ethoxyvinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.42 g), tripotassium phosphate (3.39 g), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (328 mg) and palladium(II) acetate (90 mg), and the mixture was stirred under nitrogen atmosphere at 60C for 2 hr. The reaction mixture was cooled to room temperature, and diluted with ethyl acetate, and the insoluble substance was removed by filtration. The filtrate was washed with water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (560 mg). 1H NMR (400 MHz, DMSO-d6) delta 1.28 (3H, t, J = 7.6 Hz), 3.88 (3H, s), 3.90-4.00 (2H, m), 6.27 (1H, d, J = 12.8 Hz), 7.43 (1H, d, J = 12.8 Hz), 7.60 (1H, d, J = 8.8 Hz), 8.16 (1H, d, J = 8.8 Hz) .

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1214328-96-7, Methyl 3-bromo-6-chloropicolinate, and friends who are interested can also refer to it.

Reference:
Patent; Takeda Pharmaceutical Company Limited; YOGO, Takatoshi; YOSHIKAWA, Masato; SAITOH, Morihisa; KATOH, Taisuke; SEKI, Tomohiro; NAKADA, Yoshihisa; (148 pag.)EP3366684; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 73583-41-2, 4-Bromo-3-chloropyridine, 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, 73583-41-2, blongs to pyridine-derivatives compound. Recommanded Product: 4-Bromo-3-chloropyridine

Step c: To a solution of tert-butyl (i-(6-amino-5-mercaptopyrazin-2-yl)-4-methylpiperidin-4-yl)carbamate(44 mg, 0.130 mmol), 4-bromo-3-chloropyridine (31.2 mg, 0.162 mmol), XantPhos (7.5 mg, 0.013 mmol), and Pd2 (dba)3 (5.9 mg, 0.0065 mmol) in dioxane (2 mL) was added (at RT and under N2) DIPEA (68 IL, 0.389 mmol). The resulting solution was stirred in a microwave reactor for 1 h at 110 C. and for 1 h at 125 C. After cooling to RT, the reaction was diluted with EtOAc and it was filtered through a pad of Celite followed by EtOAc (5 mL) wash. The volatiles were removed under reduced pressure. The result-ing residue was dissolved in DCM (3 mE) and it was treated with TFA (500 IL). The resulting mixture was stirred for 10 mm at RT. The volatiles were removed under reduced pressure and the resulting residue was purified by HPLC (gradient elution 15-40% acetonitrile in water, 5 mM NH4OH modifier) to give 6-(4-amino-4-methylpiperidin-1 – yl)-3-((3-chloropyridin-4-yl)thio)pyrazin-2-amine (8.5 mg, 0.024 mmol). ?H NMR (400 MHz, METHANOL-d4) oe 8.30 (s, 1H), 8.06 (d, J=5.56 Hz, 1H), 7.52 (s, 1H), 6.58 (d, J=5.31 Hz, 1H), 3.76 (ddd, J=13.64, 7.07, 4.29 Hz, 2H), 3.44-3.59 (m, 2H), 1.45-1.64 (m, 4H), 1.09-1.23 (m, 3H). HRMS calcd for C,5H2QC1N65 (M+H) 351.1159. found 351.1159. IC50 is 0.076 tM.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,73583-41-2, its application will become more common.

Reference:
Patent; NOVARTIS AG; Chen, Zhuoliang; Dore, Michael; Fortanet, Jorge Garcia; Karki, Rajesh; Kato, Mitsunori; LaMarche, Matthew J.; Perez, Lawrence Blas; Williams, Sarah; Sendzik, Martin; (63 pag.)US2017/1975; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 76015-11-7 ,Some common heterocyclic compound, 76015-11-7, molecular formula is C7H9NO2, 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.

REFERENCE EXAMPLE 2 3-Methoxy-2-methyl-4(1H)-pyridone (5.6 g) was suspended in phosphorus oxychloride (50 ml), refluxed for 10 hours, and concentrated. To the resultant residue was added toluene and the residual phosphorus oxychloride was evaporated under reduced pressure. To the resultant oily substance were added chloroform and water and the chloroform layer was separated. The aqueous layer was made alkaline with potassium carbonate and extracted with chloroform. The chloroform solutions thus obtained were combined, washed with water, dried, and evaporated. The residue was purified by column chromatography on silica gel, to give 4-chloro-3-methoxy-2-methylpyridine (4.8 g) as a light brown oil. NMR(CDCl3) delta: 2.53(3H, s), 3.84(3H, s), 7.14(1H, d, J=6 Hz), 8.12(1H, d, J=6 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,76015-11-7, its application will become more common.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US4738975; (1988); A;,
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. 23612-36-4, name is 3-Bromo-1H-pyrrolo[3,2-c]pyridine. A new synthetic method of this compound is introduced below., Computed Properties of C7H5BrN2

To a mixture of Intermediate 1 (1.80 g, 9.14 mmol) in DCM (60 mL) was added di-tert- butyl dicarbonate (2.18 g, 10.0 mmol) followed by 4-dimethylaminopyridine (122 mg, 1.00 mmol). After 80 min the solution was diluted with DCM (20 mL) and washed with 0.1 M HC1 (25, 10 mL) and brine. The organic layer was dried (Na2S04), filtered and evaporated to yield the title compound as a light yellow solid (2.47 g, 90%). MS (ESI+) m/z = 299 (M+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, 23612-36-4, 3-Bromo-1H-pyrrolo[3,2-c]pyridine.

Reference:
Patent; Proximagen Limited; EVANS, David; CARLEY, Allison; STEWART, Alison; HIGGINBOTTOM, Michael; SAVORY, Edward; SIMPSON, Iain; NILSSON, Marianne; HARALDSSON, Martin; NORDLING, Erik; KOOLMEISTER, Tobias; WO2011/113798; (2011); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 766557-60-2, 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. 766557-60-2, name is 2-Ethoxy-3-iodopyridine, molecular formula is C7H8INO, 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.

An excess of saturated ammonium chloride solution was added, followed by ethyl acetate, the mixture being stirred for 5 minutes. The aqueous phase was separated off and extracted with ethyl acetate (2*). The combined organic phases were washed with water (2*), and the solvent was removed in vacuo. During this, unreacted 5-iodoisatin precipitated first from the still dilute solution and was separated off. After further concentration, finally the title compound also crystallized. The suspension was stored in a refrigerator at 5 C. for 2 hours. The precipitated, pale yellow solid was then filtered off and washed with a little ethyl acetate. After drying at 40 C., (±)-3-(2-ethoxypyridin-3-yl)-3-hydroxy-5-iodo-1,3-dihydro-2H-indol-2-one (17.1 g, 43.16 mmol, 57%) was isolated. ESI-MS [M+H+]=397.05 calculated for C15H13IN2O3=396.19

According to the analysis of related databases, 766557-60-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Abott GmbH & Co KG; US2011/65720; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 358780-14-0, Adding some certain compound to certain chemical reactions, such as: 358780-14-0, name is 1-(6-(Trifluoromethyl)pyridin-3-yl)ethanone,molecular formula is C8H6F3NO, 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 358780-14-0.

In methanol (30.0 mL), 10.3 mmol l-[6-(Trifluoromethyl)-3- pyridinyl]ethanone is dissolved. Sodium borohydride (584 mg, 15.4 mmol) is added and the mixture is stirred at 0C for 30 minutes. The solvent is evaporated under reduced pressure and water is added. Extraction with ethyl acetate, washing with saturated brine and drying over anhydrous sodium sulfate is performed. After filtration, the solvent in the filtrate is evaporated under reduced pressure.

According to the analysis of related databases, 358780-14-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SOLVAY SA; BRAUN, Max Josef; (21 pag.)WO2017/198812; (2017); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 73583-41-2 ,Some common heterocyclic compound, 73583-41-2, molecular formula is C5H3BrClN, 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: Toluene/tert-butanol(6 mL, v/v, 5:1) was added to the mixture of 4-piperidone ketal(1.0 mmol, 1.0 equiv), aryl bromide 15af. (1.1 mmol, 1.1 equiv),sodium tert-butoxide (1.0 mmol, 1.0 equiv), palladium diacetate(0.05 mmol, 0.05 equiv), and X-Phos (0.05 mmol, 0.05 equiv), andthe mixture was stirred in a microwave reactor under argon for15 min at 160 C. After the reaction vials were cooled to roomtemperature and filtered over celite, they were rinsed well withethyl acetate. The filtrate was subsequently evaporated underreduced pressure to obtain the compounds 16a-f.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,73583-41-2, its application will become more common.

Reference:
Article; Wang, Zhengyu; Shi, Xiaofan; Zhang, Huan; Yu, Liang; Cheng, Yanhua; Zhang, Hefeng; Zhang, Huibin; Zhou, Jinpei; Chen, Jing; Shen, Xu; Duan, Wenhu; European Journal of Medicinal Chemistry; vol. 139; (2017); p. 128 – 152;,
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. 1211518-35-2, name is Methyl 6-chloro-5-(trifluoromethyl)picolinate. A new synthetic method of this compound is introduced below., Quality Control of Methyl 6-chloro-5-(trifluoromethyl)picolinate

d) 6-Cyclopropylmethoxy-5-trifluoromethyl-pyridine-2-carboxylic acid Sodium hydride (1.1 g, 31.4 mmol) was added in portions to cyclopropylmethanol (20 mL) and the mixture was stirred at room temperature for 0.5 hours. 6-Chloro-5-(trifluoromethyl)-pyridine-2-carboxylic acid methyl ester (1.5 g, 6.3 mmol) was added and the resulting solution was stirred at 80 C for 1 h. Water (20 mL) was added; the solution was acidified with 6 N hydrochloric acid and then concentrated to give a residue which was partitioned between water (30 mL) and ethyl acetate (20 mL). The aqueous solution was extracted with ethyl acetate (2 x 20 mL) and the combined organic phase was washedwith brine (20 mL), dried over anhydrous sodium sulfate, filtered and concentrated to give the crude target compound. The crude target compound was purified by column chromatography (silica gel, 10 g, 15% ethyl acetate in petroleum ether) to give the title compound (1.4 g, 85%) as white solid; MS (El): mle = 262.0 [MH?i.

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, 1211518-35-2, Methyl 6-chloro-5-(trifluoromethyl)picolinate.

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

Electric Literature of 79491-46-6 ,Some common heterocyclic compound, 79491-46-6, molecular formula is C6H4Br2N2O3, 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.

E4. 2-Bromo-5,6-dimethoxy-3-nitropyridine 20 g of 2,6-dibromo-3-methoxy-5-nitropyridine (example E3) are dissolved in 550 ml of anhydrous methanol at 30-40 C. 4.6 g sodium methoxide dissolved in 30 ml anhydrous methanol is added to this solution. The reaction mixture is stirred for one hour at room temperature, poured into 700 ml of water and stored in the refrigerator overnight. The precipitate is filtered, washed with ice cold water and dried under vacuum to yield the title compound. 1H NMR (400 MHz, CDCl3): delta = 3.95 (s, 3H), 4.12 (s, 3H), 7.69 (s, 1 H). 13C NMR (100 MHz, CDCl3): delta = 55.68, 56.73, 115.33, 121.89, 143.18, 155.10.

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. 79491-46-6, 2,6-Dibromo-3-methoxy-5-nitropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; 4SC AG; EP2017277; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 107867-51-6, 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 107867-51-6 as follows.

Unpurified 5-(trifluoromethyl)pyridin-2,3-diamine was added to diethyl oxalate (10.0 mL). The mixture was stirred at 120 C. for 12 hours and then cooled to room temperature. Et2O was added thereto to form a solid, and the formed solid was filtered under reduced pressure to obtain brown solid compound of 7-(trifluoromethyl)pyrido[2,3-b]pyrazin-2,3-diol. The mixture of unpurified 7-(trifluoromethyl)pyrido[2,3-b]pyrazin-2,3-diol and POCl3 (10.0 mL) was stirred at 130 C. for 12 hours and then cooled to room temperature. The reaction mixture was poured into ice water to form a solid. The formed solid was filtered and then dried under reduced pressure to obtain brown solid compound of 2,3-dichloro-7-(trifluoromethyl)pyrido[2,3-b]pyrazine (370.0 mg, 53% in 3 steps).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,107867-51-6, its application will become more common.

Reference:
Patent; C&C RESEARCH LABORATORIES; Ho, Pil Su; Yoon, Dong Oh; Han, Sun Young; Lee, Won Il; Kim, Jung Sook; Park, Woul Seong; Ahn, Sung Oh; Kim, Hye Jung; US2014/315888; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem