Pyridine-derivatives

Related Products of 1256810-26-0 ,Some common heterocyclic compound, 1256810-26-0, molecular formula is C7H6BrNO3, 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 mixture of 6-bromo-3-methoxypicolinic acid (1.84 g, 7.93 mmol) and 3- fluorobenzene-l,2-diamine (1.0 g, 7.93 mmol) was stirred in PPA (3 mL) on a pre-heated oil- bath at 120 C for 14 h. The mixture was poured to ice-water and basified to pH = 8 with Na2C03. Then the mixture was filtrated to collect the brown solid as 6-bromo-2-(4-fluoro-lH- benzo[d]imidazol-2-yl)pyridin-3-ol (900 mg, yield: 37%). The filtrated was extracted with ethyl acetate, and the organic layer was washed with brine and dried over Na2S04. After concentrated, the residue was purified by column chromatography to give the product of 2-(6-bromo-3- methoxypyridin-2-yl)-4-fluoro-lH-benzo[d] imidazole (350 mg, yield: 14%). 1H- MR (CDC13, 400 MHz) delta 10.43-10.56 (m, 1H), 7.46 (d, J= 8.8 Hz, 1H), 7.33 (d, J= 8.8 Hz, 1H), 7.21-7.30 (m, 2H), 6.90-6.98 (m, 1H), 4.05 (s, 3H). MS (M+H) : 322 / 324.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1256810-26-0, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; HE, Shuwen; DAI, Xing; PALANI, Anandan; NARGUND, Ravi; LAI, Zhong; ZORN, Nicolas; XIAO, Dong; DANG, Qun; LI, Peng; PENG, Xuanjia; SOLL, Richard; WO2014/121418; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 81803-60-3 ,Some common heterocyclic compound, 81803-60-3, molecular formula is C10H10N2O2, 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 an ice cold solution of ethyl imidazo[l,5-alpha]pyridine-3-carboxylate (10 g, 52.6 mmol) in acetonitrile (500 mL) was added N-bromo succinimide (9.36 g, 52.6 mmol). The mixture was allowed to stir for 1 h at which time triethylamine (10 mL) was added to the deep red- violet solution. The color dissipated and the solution was concentrated. Purification of the crude solid by silica gel chromatography (0-20% EtOAc/Hexanes) provided a white crystalline solid (13.5 g 95%). MS 268.9 (M + 1)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,81803-60-3, its application will become more common.

Reference:
Patent; MERCK & CO., INC.; WO2008/85302; (2008); 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 77618-99-6, name is 2-Amino-5-(methylthio)pyridine. This compound has unique chemical properties. The synthetic route is as follows. name: 2-Amino-5-(methylthio)pyridine

Step 2: 4-Chloro-7-[5-(methylthio)-2-pyridinyl]-6,7-dihydro-5H-pyrrolo[2,3- cflpyrimidine (200)To a stirred solution of (4,6-dichloro-5-pyrimidinyl)acetaldehyde 209 (see example 116, step 1 , 3.41 g, 17.8 mmol) in MeOH (180 mL) was added 199 (3.0 g, 21.4 mmol) at RT. The reaction mixture was cooled to -15 0C with an ice/methanol bath and glacial acetic acid (3.1 mL, 53.4 mmol) and NaBH3CN (3.35 g, 53.4 mmol) were added. The reaction mixture was stirred at -15 0C for 15 min then allowed to warm to RT and stir for 19 h. The reaction mixture was then diluted with water (50 mL) and extracted with CH2CI2 (3 x 100 mL). The combined organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure to a yellow oil. The crude oil was dissolved in THF (500 mL) with stirring and then f-BuOK (5.99 g, 53.4 mmol) was added in one portion at RT. The reaction mixture changed immediately to a brown color and was stirred at RT for 22 h. The reaction mixture was quenched with water (50 mL), concentrated under reduced pressure, and then redissolved in EtOAc (200 mL). The organic layer was washed with water (1 x 50 mL) and the aqueous layer was extracted with EtOAc (2 x 100 ml_). The combined organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure to a brown oil. The crude oil was purified using SiO2 flash chromatography (20% to 40% EtOAc in hexanes; monitored at 319 nm) to give 550 mg (1 1%) of the title product 200 as a colorless oil. 1H NMR (400 MHz, CDCI3): delta 8.57 (d, J = 9.0 Hz, 1 H), 8.43 (s, 1 H), 8.29 (d, J = 2.4 Hz, 1 H), 7.68 and 7.66 (dd, J1 = 8.8 Hz, J2 = 2.4 Hz, 1 H), 4.37 – 4.33 (m, 2 H), 3.16 (t, J = 8.8 Hz, 2 H), 2.47 (s, 3 H).

With the rapid development of chemical substances, we look forward to future research findings about 77618-99-6.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/8895; (2008); 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 84487-15-0, name is 2-Bromo-5-nitropyridin-4-amine. This compound has unique chemical properties. The synthetic route is as follows. Safety of 2-Bromo-5-nitropyridin-4-amine

Synthesis of 323-1. To a mixture of 323-0 (1.00 g, 4.6 mmol), 4-fluorophenylboronic acid (773 mg, 5.5 mmol) and Cs2CO3 (3.00 g, 9.2 mmol) in dioxane/H2O (20 mL/4 mL) was added Pd(PPh3)4 (531 mg, 0.5 mmol) under N2 atmosphere. The mixture was stirred at 95 C for 2 hours and then concentrated in vacuo. The residue was dissolved with EtOAc (60 mL) and the resulting solution was washed with brine (20 mL × 3). The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography on silica gel (DCM : MeOH = 100 : 1 ~ 50 : 1) to give 323-1 (1.00 g, 93 %) as a yellow solid.

With the rapid development of chemical substances, we look forward to future research findings about 84487-15-0.

Reference:
Patent; RODIN THERAPEUTICS, INC; JEFSON, Martin, R.; LOWE, John, A., III; DEY, Fabian; BERGMANN, Andreas; SCHOOP, Andreas; FULLER, Nathan, Oliver; (165 pag.)WO2017/7756; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 92992-85-3, 2-Bromo-3,5-dimethylpyridine, 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, 92992-85-3, blongs to pyridine-derivatives compound. Quality Control of 2-Bromo-3,5-dimethylpyridine

To 2-bromo-3,5-dimethylpyridine (10.26 g) were added (S)-1-(tert-butoxycarbonyl)-3-aminopyrrolidine (10.27 g),tris(dibenzylideneacetone)dipalladium(0)(505 mg),2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (1 g),sodium tert-butoxide (7.24 g) and toluene (180 mL) and the mixture was stirred at 80c for 3 hr. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was concentrated under reduced pressure and the obtained residue was purified by column chromatography (hexane:ethyl acetate). The solvent was evaporated,ethyl acetate (50 mL),4N hydrogen chloride/1,4-dioxane solution (50 mL) and methanol (10 mL) were added to the obtained residue,and the mixture was stirred at room temperature for 2.5 hr. To the reaction mixture was added diethyl ether,and the supernatant was removed by decantation. To the obtained residue was added ethyl acetate/ethanol,and the precipitate was collected by filtration to give the title compound (11.9 g). MS(ESI)m/z:192(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,92992-85-3, its application will become more common.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; ISHIBUCHI, Seigo; SARUTA, Kunio; HAMADA, Maiko; MATOBA, Nobuatsu; MATSUDAIRA, Tetsuji; SEKI, Maki; TARAO, Akiko; HONJO, Takashi; OGATA, Shingo; KAWATA, Atsushi; MOROKUMA, Kenji; FUJIE, Naoto; AOYAMA, Yukio; (251 pag.)EP3321256; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 23056-40-8, 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. 23056-40-8, name is 2-Chloro-5-methyl-3-nitropyridine, molecular formula is C6H5ClN2O2, 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.

To a mixture of 4 (1.0 g, 6.5 mmol) and c-H2SO4 (27 mL), sodium dichromate (2.5 g) was added slowly. After stirring at rt for 15 h, the mixture was slowly added into cracked ice. The mixture was extracted with EtOAC. The organic extract was washed with brine, dried over Na2SO4, and evaporated in vacuo to provide product 5 as a green solid (1.0 g, 85%). 1H NMR (300 MHz, DMSO-d6) delta: 13.32 (s, 1H), 8.64 (d, J = 2.4 Hz, 1H), 8.37 (d, J = 2.4 Hz, 1H).

According to the analysis of related databases, 23056-40-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhao, Chao; Yang, Su Hui; Khadka, Daulat Bikram; Jin, Yifeng; Lee, Kyung-Tae; Cho, Won-Jea; Bioorganic and Medicinal Chemistry; vol. 23; 5; (2015); p. 985 – 995;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 6945-67-1, 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.6945-67-1, name is 2-Bromo-4-nitropyridine, molecular formula is C5H3BrN2O2, molecular weight is 202.99, as common compound, the synthetic route is as follows.

Into a 250-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a mixture of 4-[[4-nitro-3-(trifluoromethyl)phenyl] amino]cyclohexan-l-ol (12 g, 39 mmol, 1.3 eq.) in N-dimethylformamide (100 mL), sodium hydride (1.9 g, 79 mmol, 2 eq.), and 2-bromo-4-nitropyridine (6.2 g, 31 mmol). The resulting solution was stirred for 1.5 hours at room temperature in an oil bath. The reaction was then quenched by the addition of 200 mL of water. The resulting solution was diluted with 200 mL of ethyl acetate. The resulting mixture was washed with water and then brine. The organic layer was dried over anhydrous sodium sulfate. The solids were filtered out and the solution was concentrated under vacuum to provide 10 g (56%) of aniline as a yellow solid.

The chemical industry reduces the impact on the environment during synthesis 6945-67-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERIAL INC.; LONG, Alan; WILKINSON, Douglas, Edward; (224 pag.)WO2016/118638; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 58327-75-6, 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. 58327-75-6, name is 3-Aminothieno[2,3-b]pyridine-2-carboxylic acid, molecular formula is C8H6N2O2S, 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.

A solution of 238 (17 g, 87 mmoi) in phosphoc acid (150 mL, 85% aqueous solution) is stirred at 100 C for 45 minutes. Saturated aqueous sodium bicarbonate solution is then added at room temperature to adjust to pH 8. The solid is collected by filtration and washed with EtOH (100 mL x 2) to give US as an orange solid (9.0 g, 54% yield). (MS:[M+H] 152.1)

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 58327-75-6, 3-Aminothieno[2,3-b]pyridine-2-carboxylic acid.

Reference:
Patent; IMMUNE SENSOR, LLC; THE BOARD OF REGENTS OF THE UNIVERSITY OF TEXAS SYSTEM; ZHONG, Boyu; SUN, Lijun; SHI, Heping; LI, Jing; CHEN, Chuo; CHEN, Zhijian; (270 pag.)WO2017/176812; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1111637-94-5 ,Some common heterocyclic compound, 1111637-94-5, molecular formula is C8H7BrN2, 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 solution of 19 (205.4 mg, 0.909 mmol) and 40 (150 mg, 0.909 mmol) in toluene/ ethanol (4 mL: 1 mL) was added sodium carbonate (190.8 mg, 1.818 mmol). The reaction was degassed and purged with nitrogen for 10 min. Pd(dppf)Cl2 (37.1 mg, 0.0454 mmol) was added to the reaction, which was degassed and purged with nitrogen for another 10 min, heated to 90 C. under sealed condition overnight, then allowed to cool to rt, and diluted with chloroform. The organic layer was filtered through Celite plug and concentrated to get the crude, which was purified through flash chromatography by using 100-200 mesh silica gel. The compound was eluted in 50% ethyl acetate in hexane as off-white solid 88.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1111637-94-5, its application will become more common.

Reference:
Patent; ARRIEN PHARMACEUTICALS LLC; Vankayalapati, Hariprasad; Yerramreddy, Venkatakrishnareddy; Gangireddy, Paramareddy; Appalaneni, Rajendra P.; US2014/315909; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1074-98-2 ,Some common heterocyclic compound, 1074-98-2, molecular formula is C6H6N2O3, 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.

3-Methyl-4-nitro-pyridine-N-oxide (5.34 g, 34.7 mmol, 1 equiv.) and N,N-dimethylformamide diethyl acetal (10.5 mL, 61.4 mmol, 1.8 equiv.) were combined in 50 mL anhydrous DMF and heated to 120 C. for 3 h. The reaction was allowed to cool back to room temperature and the DMF solvent was removed in vacuo. The residue was treated with ~80 mL toluene, which was then removed in vacuo as well. Finally the residue was mixed with benzene and filtered. The desired vinyl amine was obtained as a dark purple solid (6.74 g, 32.2 mmol, 93%), which was used as is in the next step. The vinyl amine from above (3.37 g, 16.1 mmol, 1 equiv.) and 1.75 mL of water were mixed in 50 mL EtOH. Ammonium formate (4.56 g, 72.5 mmol) and 10% palladium-on-carbon (600 mg) were added and the mixture was heated to a gentle reflux for 1 h. TLC and MS (ES+) revealed no starting material but showed the presence of two major components, the desired 5-aza-indole and its N-oxide. The reaction was left stirring for a further 2 h after more ammonium formate and more palladium catalyst were added. Finally the reaction was cooled to room temperature, filtered and solvents removed in vacuo. 5% NaOH aqueous solution was added and the mixture was extracted with EtOAc. The combined organics were dried (MgSO4), filtered, and the solvent was removed in vacuo, providing 0.555 g of desired 5-aza-indole (4.70 mmol, 29% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1074-98-2, its application will become more common.

Reference:
Patent; Boehringer Ingelheim Pharmaceuticals, Inc.; US2003/162968; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem