Category: pyridine-derivatives

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. 920966-03-6, name is 4-Chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid, the common compound, a new synthetic route is introduced below. Quality Control of 4-Chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid

To a stirred solution of 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid (0.8 g, 4.06 mmol) in propan-2-ol (20 mL) was added concentrated sulphuric acid (0.5 mL) at 0 C. and the reaction mixture was stirred at 80 C. for 12 hours. The reaction mixture was cooled to ambient temperature and concentrated in vacuo. The crude product was dissolved in water, basified with saturated bicarbonate and extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. The crude material was purified by flash column chromatography (20% ethyl acetate/hexane) to provide isopropyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate as a white solid (0.3 g, 33% yield): MS (ES) m/z 239.1 (M+H).

The synthetic route of 920966-03-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACLARIS THERAPEUTICS, INC.; ANDERSON, David Randolph; HOCKERMAN, Susan Landis; BLINN, James Robert; JACOBSEN, Eric Jon; US2019/135807; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 823221-93-8, 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 823221-93-8, name is 5-Bromo-2-chloro-4-(trifluoromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows.

A solution of Compound 40a (3.10 g, 11.90 mmol) and sodium thiomethoxide (918 mg, 13.09 mmol) in dioxane (30 mL) was stirred for 16 hr at 110 C. After completion of the reaction, the reaction mixture was poured into water (150 mL), and the resulting mixture was extracted with ethyl acetate (100 mL×2). The organic phases were combined, washed with saturated brine (100 mL), dried over anhydrous sodium sulfate, filtered, and concentrated to give Compound 40b (2.91 g). 1H NMR (400MHz, CDCl3) delta8.66 (s, 1H), 7.43 (s, 1H), 2.57 (s, 3H).

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 823221-93-8, 5-Bromo-2-chloro-4-(trifluoromethyl)pyridine.

Reference:
Patent; Chia Tai Tianqing Pharmaceutical Group Co., Ltd.; Medshine Discovery Inc.; CHEN, Bin; YAO, Yuanshan; CHEN, Yuan; LI, Ao; XU, Ran; HUANG, Zhensheng; TIAN, Dongdong; LI, Hongwei; YANG, Chengshuai; LI, Jian; CHEN, Shuhui; (69 pag.)EP3489235; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 887115-56-2, 5-Bromo-1-methyl-1H-pyrazolo[3,4-b]pyridine, 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, 887115-56-2, blongs to pyridine-derivatives compound. name: 5-Bromo-1-methyl-1H-pyrazolo[3,4-b]pyridine

Step 2 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazolo[3,4-b]pyridine (compound 4-3) Compound 4-2 (3.1 g, 14.6 mmol) and bis(pinacolato) borate (11.1 g, 43.8 mmol) were added into a 250 ml reaction flask, and DMF (150 ml) and potassium acetate (4.3 g, 43.8 mmol) was added. After the air of reaction system was replaced by argon for three times, Pd(dppf)Cl2 (0.55 g, 0.73 mmol) was added, and then the air was replaced with nitrogen for another three times. The reaction system was heated to 90 C., and stirred for 8 h. The reaction progress was monitored by LC-MS. After completion of the reaction, the reaction solution was filtered, the filter cake was washed with EA (30 ml*3), and the filtrate was concentrated under reduced pressure to remove DMF and give compound 4-3 (13.5 g) as brown solid which was used directly in next reaction. MS m/z (ESI): 260.2 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,887115-56-2, its application will become more common.

Reference:
Patent; SHANGHAI HAIYAN PHARMACEUTICAL TECHNOLOGY CO. LTD.; YANGTZE RIVER PHARMACEUTICAL GROUP CO., LTD.; LAN, Jiong; JIN, Yunzhou; ZHOU, Fusheng; XIE, Jing; SHEN, Sida; HU, Yi; LIU, Wei; LV, Qiang; (96 pag.)US2017/8889; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 936011-17-5 , The common heterocyclic compound, 936011-17-5, name is 5-Bromo-2-methoxyisonicotinaldehyde, molecular formula is C7H6BrNO2, 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 the solution of 5-bromo-2-methoxy-pyridine-4-carbaldehyde (CAS: 936011-17-5, Vendor: Bidepharm, 25.0 g, 115.72 mmol) in methanol (500 mL) was added sulfuric acid (14.19 mL, 231.5 mmol). After being stirred at rt for 18 hrs, the mixture was concentrated and added to the mixture solvent of aq. Na2C03 (150 mL) and EA (150 mL). The mixture was separated, the organic layer was washed with brine (50 mL), dried over Na2S04 and concentrated to give compound 76a (28.0 g) as a yellow oil. MS: calc?d 262 (MH+), measured 262 (MH+).

The synthetic route of 936011-17-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; DEY, Fabian; KOU, Buyu; LIU, Haixia; SHEN, Hong; WANG, Xiaoqing; ZHANG, Weixing; ZHANG, Zhisen; ZHANG, Zhiwei; ZHU, Wei; (203 pag.)WO2019/238616; (2019); 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.169205-95-2, name is 2-(Methylthio)oxazolo[4,5-b]pyridine, molecular formula is C7H6N2OS, molecular weight is 166.2, as common compound, the synthetic route is as follows.Computed Properties of C7H6N2OS

The following 4-methyl-2-methylthiooxazolopyridinium tosylates are prepared by heating the corresponding 2-methylthiooxazolopyridines (M. Y. Chu-Moyer and R. Berger, J. Org. Chem. 60, 5721-5725 (1995)) with one equivalent of methyl tosylate at 100-110 C. for one hour.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,169205-95-2, 2-(Methylthio)oxazolo[4,5-b]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; Molecular Probes, Inc.; US6664047; (2003); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 22353-40-8, 2,3-Dichloro-5-nitropyridine, 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, 22353-40-8, blongs to pyridine-derivatives compound. Recommanded Product: 22353-40-8

Anhydrous SnCl2 (300 g, 1.58 mol) and concentrated HCl (350 mL) were charged to a 5L flask with mechanical stirrer and thermocouple. The flask was cooled in ice and the product of Example 2B (100 g, 0.518 mol) was added in portions maintaining the temperature below 65 C. After the addition was complete, the cold bath was removed, and the mixture was stirred for 2 hours at ambient temperature. The mixture was cooled in ice as 25% aqueous NaOH (1000 mL) was added to bring the mixture to pH>10. The mixture was extracted with CH2Cl2 (1*600 mL, 2*400 mL) and the combined extracts were washed with brine (200 mL), dried (MgSO4), and concentrated under vacuum. The residual solid was crystallized from a mixture of water (500 mL) and ethanol (100 mL) to provide the title compound as a solid. 1H NMR (CDCl3, 300 MHz) delta 3.80 (br s, 2H), 7.10 (d, J=3 Hz, 1H), 7.77 (d, J=3 Hz, 1H); MS (DCI/NH3) m/z 180/182/184 (M+NH4)+163/165/167 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,22353-40-8, its application will become more common.

Reference:
Patent; Buckley, Michael J.; Ji, Jianguo; US2004/242644; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 167837-43-6, name is (E)-3-(6-Aminopyridin-3-yl)acrylic acid. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 167837-43-6

The following compounds were obtained according to a similar manner to that of Example 2-(4). 2-[(E)-3-(6-Aminopyridin-3-yl)acryloylaminomethyl]-1-[2,4-dichloro-3-(2-methylquinolin-8-yloxymethyl)phenyl]pyrrole. NMR (DMSO6, delta): 2.59 (3H, s), 4.00-4.10 (1H, m), 4.19-4.21 (1H, m), 5.32-5.45 (2H, m), 6.16-6.22 (2H, m), 6.29 (1H, d, J=16 Hz), 6.38-6.45 (2H, m), 6.48 (1H, d, J=8 Hz), 6.83-6.87 (1H, m), 7.11-7.23 (2H, m), 7.37-7.48 (2H, m), 7.48-7.58 (2H, m), 7.61 (1H, d, J=8 Hz), 7.70 (1H, d, J=8 Hz), 7.99-8.09 (2H, m), 8.20 (1H, d, J=8 Hz).

With the rapid development of chemical substances, we look forward to future research findings about 167837-43-6.

Reference:
Patent; Fujisawa Pharmaceutical Co., Ltd.; US6344462; (2002); B1;,
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. 821791-58-6, name is Ethyl 4-chloro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate, the common compound, a new synthetic route is introduced below. Application In Synthesis of Ethyl 4-chloro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate

The following compounds were prepared as previously described with the addition of a chlorination step. An example of such a chlorination is described below. A mixture of 4-chloro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid ethyl ester (1.00 g, 4.64 mmol) and NCS (0.68 g, 5.10 mmol) in DMF (30 mL) was stirred for 1 hour. The reaction mixture was diluted with EtOAc and washed with 0.1 N HCl solution. The organic layer was dried (MgSO4) and concentrated under reduced pressure to give 1.10 g (95%) of 4,5-dichloro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid ethyl ester.

The synthetic route of 821791-58-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Marlow, Allison L.; Wallace, Eli; Seo, Jeongbeob; Lyssikatos, Joseph P.; Yang, Hong Woon; Blake, James; US2005/256123; (2005); 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.628691-93-0, name is 2-Chloro-3-fluoroisonicotinic acid, molecular formula is C6H3ClFNO2, molecular weight is 175.55, as common compound, the synthetic route is as follows.Product Details of 628691-93-0

Step l :A suspension of 2-chloro-3-fluoropyridine-4-carboxylic acid (CAS 628691-93-0, 2 g, 11.39 mmol) in MeOH (7 mL) and DCM (21 mL) at 0 C was treated with TMS-Diazomethane (5.70 mL, 11.39 mmol) in a drop wise fashion. The reaction was stirred at 0 C for 0.5 h. The reaction was quenched with AcOH (0.5 mL) and concentrated in vacuo. The residue was purified by flash chromatography (0-100% EtOAc in petrol on Si02) to afford methyl 2-chloro-3-fluoropyridine-4-carboxylate. 1H NMR (300 MHz, Methanol-^) delta ppm 3.97 (s, 3 H) 7.76 – 7.86 (m, 1 H) 8.29 – 8.40 (m, 1 H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,628691-93-0, 2-Chloro-3-fluoroisonicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; AHMED, Saleh; BARKER, Gregory; CANNING, Hannah; DAVENPORT, Richard; HARRISON, David; JENKINS, Kerry; LIVERMORE, David; WRIGHT, Susanne; KINSELLA, Natasha; (259 pag.)WO2016/148306; (2016); 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.62150-46-3, name is 4-Bromopicolinamide, molecular formula is C6H5BrN2O, molecular weight is 201.0207, as common compound, the synthetic route is as follows.HPLC of Formula: C6H5BrN2O

EXAMPLE 64-((4-Oxo-3-o-tolyl-3,4-dihydropyrrolo[1 ,2-tf[1 ,2,4]triazin-2- yl)methylamino)picolinamideA mixture of 2-(aminomethyl)-3-o-tolylpyrrolo[1 ,2-7[1 .2,4]triazin-4(3H)-one (102 mg, 0.4 mmol), 4-bromopicolinamide (105 mg, 0.52 mmol) and DIEA (200 mu, 1 .13 mmol) in n- butanol (2.2 mL) was reacted under microwave irradiation at 190C during 22 h. After cooled to room temperature, the mixture was concentrated in vacuum and was purified by reverse phase chromatography (C-18 silica from Waters, water/1 :1 acetonitrile- methanol as eluents [0.1 % v/v formic acid buffered] 0% to 100%) to obtain 7 mg of the title compound (4,6%).LRMS (m/z): 375 (M+1 )+.1H NMR (400 MHz, DMSO) delta 8.38 (s, 2 H), 8.01 (d, J=5.86 Hz, 1 H), 7.90 (m, 1 H), 7.61 – 7.73 (m, 1 H), 7.48 – 7.58 (m, 1 H), 7.39 – 7.48 (m, 1 H), 7.23 – 7.40 (m, 2 H), 7.03 – 7.14 (m, 1 H), 6.93 – 7.04 (m, 1 H), 6.62 (dd, J=4.30, 2.74 Hz, 1 H), 6.38 – 6.53 (m, 1 H), 3.86 – 3.99 (m, 2 H), 2.08 (s, 3 H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,62150-46-3, 4-Bromopicolinamide, and friends who are interested can also refer to it.

Reference:
Patent; ALMIRALL, S.A.; BERNAL ANCHUELA, Francisco Javier; CARRASCAL RIERA, Marta; CATURLA JAVALOYES, Juan Francisco; GRACIA FERRER, Jordi; MATASSA, Victor Giulio; TERRICABRAS BELART, Emma; TALTAVULL MOLL, Joan; ERRA SOLA, Montserrat; WO2012/146666; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem