Month: April 2022

Synthetic Route of 53636-70-7, 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 53636-70-7, name is 6-Methyl-2,3-pyridinedicarboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

In a 100 ml round-bottomed flask 6-methyl-2,3-pyridinedicarboxylic acid (10 g, 55.2 mmol) and acetic anhydride (26 ml, 276 mmol) were added and heated at 100 0C under nitrogen for 5 hours. After this time the volatiles were removed under vacuum to give the title compound D16 (8.2 g, 50.3 mmol, 91 % yield) as a slightly brown solid. 1H NMR (400 MHz, DMSO-J6) delta ppm 8.41 (d, 1 H), 7.82 (d, 1 H), 2.73 (s, 3 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 53636-70-7, 6-Methyl-2,3-pyridinedicarboxylic acid.

Reference:
Patent; GLAXO GROUP LIMITED; DI FABIO, Romano; WO2011/23578; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 13296-04-3 ,Some common heterocyclic compound, 13296-04-3, molecular formula is C11H10N2, 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 Radley reaction carousel tube, add 1 equivalent 1, 1.1 equivalents of the amine, a stir bar, and 5 mL 95% ethanol. Reflux while stirring for 24 hours. After cooling to room temperature the resulting precipitate was collected by vacuum filtration, washing with 10 mL deionized water and 5 mL chloroform.

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. 13296-04-3, 4-(Pyridin-4-yl)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Watkins, Sydney M.; Ghose, Debarati; Blain, Joy M.; Grote, Dakota L.; Luan, Chi-Hao; Clare, Michael; Meganathan; Horn, James R.; Hagen, Timothy J.; Bioorganic and Medicinal Chemistry Letters; vol. 29; 20; (2019);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 36953-37-4, 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.36953-37-4, name is 4-Bromopyridin-2(1H)-one, molecular formula is C5H4BrNO, molecular weight is 173.9954, as common compound, the synthetic route is as follows.

Under argon atmosphere, a solution of 4-bromo-1,2-dihydropyridin-2-one (1.00 g, 5.75 mmol) in THF (20 mL) was treated with sodium hydride (60% dispersion in mineral oil, 230 mg, 5.75 mmol) at 0C and then stirred 30 minutes at room temperature. Iodoethane (1.39 mL, 17.25 mmol) was added to the mixture and the reaction was stirred for 16 hours at room temperature and then heated at 50 C for 24 hours. The middle was diluted with water and ethyl acetate. The organic layer was washed with water, brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (DCM/EtOAc 100/0 to 85/15) to give compound (150a) (981 mg, 4.86 mmol, 84%).

Statistics shows that 36953-37-4 is playing an increasingly important role. we look forward to future research findings about 4-Bromopyridin-2(1H)-one.

Reference:
Patent; LABORATOIRE BIODIM; Atamanyuk, Dmytro; Chevreuil, Francis; Faivre, Fabien; Lecointe, Nicolas; Ledoussal, Benoit; Oliveira, Chrystelle; Simon, Christophe; EP2913330; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 75358-90-6 , The common heterocyclic compound, 75358-90-6, name is Ethyl 2-cyanonicotinate, molecular formula is C9H8N2O2, 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.

[0249] To a solution of ethyl 2-cyano-3-pyridinecarboxylate (2.5 g) and conc. HCl (5 mL) in 150 mL ethanol was added 10% Pd/C (wet, 250 mg) and the reaction mixture was hydrogenated using a hydrogen balloon and stirred for 12 h. The reaction was filtered through celite andethanol was evaporated to give ethyl 2-(aminomethyl)-3-pyridinecarboxylate HCl as a white solid which was used in the next step without further purification.

The synthetic route of 75358-90-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLOBAL BLOOD THERAPEUTICS, INC.; CYTOKINETICS, INC.; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; METCALF, Brian; CHUANG, Chihyuan; WARRINGTON, Jeffrey; PAULVANNAN, Kumar; JACOBSON, Matthew P.; HUA, Lan; MORGAN, Bradley; WO2013/102145; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 676339-81-4, 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.676339-81-4, name is 6-(4-Carboxyphenyl)nicotinic acid, molecular formula is C13H9NO4, molecular weight is 243.2149, as common compound, the synthetic route is as follows.

(1) Add equimolar amounts of Zn (NO3) 2.6H2O (0.149g, 0.5mmol) and H2cpn (0.12g, 0.5mmol) to 12mL DMF solvent, and then stir for 10 minutes;(2) Add the material in step 1 to a 23mL polytetrafluoroethylene reactor, maintain a constant temperature of 130 C for 72 hours under autogenous pressure, and then drop to room temperature at a rate of 5 C / h;(3) The mixture in step 2 is filtered, the crystals are collected, washed with DMF solvent and dried to obtain colorless crystals.(4) Filter the product, collect the crystals, and dry to obtain colorless crystals.The yield was calculated to be 59% based on H2cpn.

Statistics shows that 676339-81-4 is playing an increasingly important role. we look forward to future research findings about 6-(4-Carboxyphenyl)nicotinic acid.

Reference:
Patent; Zhaoqing University; Ma Deyun; Yan Peng; Zhou Yiping; Mai Xufeng; Wu Yinbing; Liu Fumeilin; Chen Lilin; (9 pag.)CN111072693; (2020); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 135450-23-6, 6-(Chloromethyl)-2-cyanopyridine, 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, 135450-23-6, blongs to pyridine-derivatives compound. HPLC of Formula: C7H5ClN2

Charge Cl-nitrile (180 g) into a rector containing THF (540 g). Charge NaT (185.7 g) to the reactor and stirred at 50 C. After reaction completion, the reactor is cooled to 0 C. In another reactor, charge t-BuOK (145.6 g) and THF (320 g). Add (S)-tetrahydrofuran-3-ol (311.9 g) into the reactor while maintaining internal temperature below 50 Cto deprotonate the alcohol. Stir until t-BuOK dissolves. Add THF-OK / THF solution into 6-(iodomethyl)picolinonitrile solution (compound 6) while maintaining internal temperature below 10 C. Stir at room temperature until reaction completion. Concentrate the solution to remove THF solvent. Add ethyl acetate (630 g) and wash by water (420 g). Extract water phase by ethyl acetate (630 g). Combine organic layer and concentrate to obtain oil crude 374 g. The residue was distilled under vaccum (P=3-4 torr, internal temperature 174 C to 188 C) to obtain (S)-6-(((tetrahydrofuran-3-yl)oxy)methyl)picolinonitrile (compound 7) as an oily product (204g, >96% purity; 74% yield)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,135450-23-6, its application will become more common.

Reference:
Patent; CORVUS PHARMACEUTICALS, INC.; BY, Kolbot; JONES, William, Benton; WOLFE, Bradley, Hamilton; (131 pag.)WO2018/183965; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 72093-04-0, name is 3-Chloro-4-methylpyridine, molecular formula is C6H6ClN, 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. Application In Synthesis of 3-Chloro-4-methylpyridine

To a solution of lithium diisopropylamide (3OmL, 2M in THF) at -70C is added under argon a solutionof 3-chloro-4-methylpyridine (6.3 8g, 1 eq, SOmmol) in 25mL THF. The mixture is stirred for 5mm at -70C and then allowed to reach -30C. Thereafter the mixture is cooled down to -70C and a solution of 2-chloro- 1 -(1 -chlorocyclopropyl)ethanone (9.1 8g, 1 .2eq, 6Ommol) in 25mL THF is added. Then the mixture is allowed to reach ambient temperature and stirred for lh. Thereafter the mixture is cooled to 0C and saturated aqueous ammonium chloride solution is added. After extraction with ethyl acetate and evaporation of the solvent the crude material is purified via column chromatography over silica gel (eluent cyclohexane / ethyl acetate gradient). After evaporation of the solvent 1 Og (73%) of 3 -chloro-4- { [2-( 1-chlorocyclopropyl)oxiran-2-yl]methyl}pyridine are obtained as colourless oil.

With the rapid development of chemical substances, we look forward to future research findings about 72093-04-0.

Reference:
Patent; BAYER CROPSCIENCE AG; HOFFMANN, Sebastian; SUDAU, Alexander; DAHMEN, Peter; WACHENDORFF-NEUMANN, Ulrike; BERNIER, David; LACHAISE, Helene; BRUNET, Stephane; VIDAL, Jacky; GENIX, Pierre; COQUERON, Pierre-Yves; GEIST, Julie; VORS, Jean-Pierre; KENNEL, Philippe; MILLER, Ricarda; WO2014/167008; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 73406-50-5, Ethyl 3-hydroxypicolinate, 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, Computed Properties of C8H9NO3, blongs to pyridine-derivatives compound. Computed Properties of C8H9NO3

EXAMPLE 2 Preparation of ethyl 3-(4,6-dimethoxypyrimidin-2-yl)oxy picolinate (Compound No. 2) To 0.5 g of 60% sodium hydride, 50 ml of hexane was added, and subjected to decantation. Then, the mixture was suspended in 30 ml of dimethylformamide. To the dimethylformamide suspension, 1.9 g of ethyl 3-hydroxypicolinate was gradually added, and the 2.0 g of 2-chloro-4,6-dimethoxypyrimidine was added. The mixture was heated and stirred at a reaction temperature of from 130 to 140 C. for 4 hours. After cooling, the reaction solution was poured into water, and extracted with ethyl acetate. The extract was washed with water and dried over magnesium sulfate. Ethyl acetate was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 1.4 g of ethyl 3-(4,6-dimethoxypyrimidin-2-yl)oxy picolinate. (Yield: 40%, pale yellow liquid, refractive index nD20 =1.5389)

The synthetic route of 73406-50-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kumiai Chemical Industry Co., Ltd.; Ihara Chemical Industry Co., Ltd.; US4832729; (1989); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 22282-70-8 ,Some common heterocyclic compound, 22282-70-8, molecular formula is C5H3FIN, 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; 4-iodopyridin-2-amine2-Fluoro-4-iodopyridine (11.2 g, 50 mmol) obtained in Reference Example 1 and 28% aqueous ammonia solution (100 ml) were stirred at 150 C. for 3 hr in a sealed tube. The mixture was extracted with ethyl acetate. The extract was washed with water, and dried over anhydrous sodium hydrogensulfate. The solvent was evaporated under reduced pressure. The obtained residue was crystallized from ethyl acetate to give the title compound (6.6 g, yield 60%). melting point 167-168 C.1H-NMR (CDCl3) delta: 4.34 (2H, brs), 6.92 (1H, d, J=1.4 Hz), 6.99 (1H, dd, J=5.5, 1.4 Hz), 7.73 (1H, d, J=5.5 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,22282-70-8, its application will become more common.

Reference:
Patent; Takeda Pharmaceutical Company Limited; US2011/39893; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 920966-03-6, 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.920966-03-6, name is 4-Chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid, molecular formula is C8H5ClN2O2, molecular weight is 196.59, as common compound, the synthetic route is as follows.

Preparation 32To a solution of 4-chloro-lH-pyrrolo[2, 3-b]pyridine-5- carboxylic acid (840mg) inN,N-dimethylformamide (8.4mL) were added 1-hydroxybenzotriazole (808 mg) and 1- (3-dimethylaminopropyl) – 3-ethylcarbodiimide (929 mg) . The mixture was stirred at 600C for 30 minutes. The solution was cooled to ambient temperature and added EPO 28% ammonium hydroxide aqueous solution (1.2 ?iL) . The mixture was stirred at ambient temperature for 1 hour. To the solution were added water and chloroform and the mixture was extracted with chloroform.The extract was dried over MgSO4, filtrated and evaporated. The residue was purified by column chromatography on silica gel with chloroform and methanol (100:0 to 90:10) to give 4-chloro- lH-pyrrolo [2, 3-b]pyridine-5-carboxamide (90 mg) as a pale yellow powder.1H-NMR (DMSO-d6) delta : 6.55-6.57 (lH,m) , 7.63-7.66 (lH,m) , 7.90 (2H,br) ,8.2 9(lH,s) ,12.16(lH,brs) .MS (ESI) :m/z 218(M+Na)+.

Statistics shows that 920966-03-6 is playing an increasingly important role. we look forward to future research findings about 4-Chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid.

Reference:
Patent; ASTELLAS PHARMA INC.; WO2007/7919; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem