Pyridine-derivatives

Reference of 1211518-35-2, 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. 1211518-35-2, name is Methyl 6-chloro-5-(trifluoromethyl)picolinate, molecular formula is C8H5ClF3NO2, 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 mixture of methyl 6-chloro-5-(trifluoromethyl)pyridine-2-carboxylate (see procedure 2, step B) (200 mg; 0.83 mmol), morpholine (73 muL; 0.83 mmol); N,N-diisopropylethylamine (159 muL; 0.92 mmol) and 3 mL of dimethyl sulfoxide is stirred for 1 hour at 120C. The reaction is quenched with methanol, filtered and purified by reverse phase chromatography-HPLC (modifier: trifluoroacetic acid). (0398) Yield: 110 mg (45 % of theory) (0399) Mass spectrometry (ESI+): m/z = 291 [M+H]+ (0400) HPLC (Method 3): Retention time = 1.021 min

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

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; TRIESELMANN, Thomas; GODBOUT, Cedrickx; HOENKE, Christoph; VINTONYAK, Viktor; (130 pag.)WO2019/149660; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 130473-26-6, 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 130473-26-6 as follows.

1H-Pyrrolo[2,3-c]pyridine-5-carbaldehyde (500 mg, 3.42 mmol) is dissolved in 1.5 ml formic acid. The solution is cooled in an ice bath, is treated drop-wise with 30% aqueous hydrogen peroxide (722 muL, 6.8 mmol), is stirred 1 h in an ice bath, and allow to stand overnight at 5 C. The mixture is diluted with water, the solid is collected, washed with water and is dried to give 522 mg of an off-white solid. The formate salt is combined with 7 ml water, is diluted with 3 ml 2N NaOH, and the pH is adjusted to 3 with 5% aqueous HCl. The precipitate is collected and is dried to give 370 mg (67%) of 1H-pyrrolo[2,3-c]pyridine-5-carboxylic acid. HRMS (FAB) calcd for C8H6N2O2+H: 163.0508, found 163.0507 (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,130473-26-6, its application will become more common.

Reference:
Patent; Wishka, Donn G.; Walker, Daniel Patrick; Corbett, Jeffrey W.; Reitz, Steven Charles; Rauckhorst, Mark R.; Groppi JR., Vincent E.; US2003/105089; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 73455-13-7, 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. 73455-13-7, name is 4,5-Dichloropicolinic acid, molecular formula is C6H3Cl2NO2, 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 mixture of HATU (0.15 g, 0.41 mmol), 4,5-dichloropyridine-2-carboxylic acid (39 mg, 0.20 mmol) and (2S)-2-(methoxymethyl)pyrrolidine (1.32 mL, 1.02 mmol) was stirred at 25 00 for 16h. HPLC purification gave (4,5-dichloro-2-pyridyl)-[(2S)-2- (methoxymethyl)pyrrolidin-1-yl]methanone (39 mg) as a colourless oil. LCMS (Method T2) Rt= 1.39 mins, mlz 289.1 [M+H]. NMR showed two rotamers: RotamerA: 1H NMR (500 MHz, Methanol-d4) delta 8.71 (5, 1H), 7.96 (5, 1H), 4.44-4.38 (m, 1H), 3.82-3.75 (m, 1H), 3.68-3.64(m, 2H), 3.40 (5, 3H), 2.14-1.96 (m, 5H).

According to the analysis of related databases, 73455-13-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; BELLENIE, Benjamin Richard; CHEUNG, Kwai Ming Jack; DAVIS, Owen Alexander; HOELDER, Swen; HUCKVALE, Rosemary; LLOYD, Matthew Garth; (360 pag.)WO2018/215798; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 90145-48-5, 5-Bromopyridine-2-carboxamide, 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, Safety of 5-Bromopyridine-2-carboxamide, blongs to pyridine-derivatives compound. Safety of 5-Bromopyridine-2-carboxamide

Example 10Preparation of 5-bromo-N-(2,2,2-trichloro-1 -(4- ethylcvcloheylamino)ethyl)picolinamide(Compound-46) and 5-bromo-N-(2,2,2-trichloro-1 -(4- ethylcvclohexylamino)ethyl)picolinamide (Compound-47)[00147] 5-Bromopicolinamide 112 (1 .29 g, 6.4 mmol) and chloral (1 .25 mL) in dioxane (10 mL) were heated to 100 C. The mixture was concentrated to give 5- bromo-N-(2,2,2-trichloro-1 -hydroxyethyl)picolinamide 122 (99%).[00148] A solution of 5-bromo-N-(2,2,2-trichloro-1 -hydroxyethyl)picolinamide 122 (0.83 g, 2.39 mmol) in chloroform (20 mL) was reacted with PCI5 (0.51 g, 2.33 mmol) at 50 C for 30 minutes. The mixture was cooled to -78 C and 4- ethylcyclohexanamine was added (1 g, 7.5 mmol). After 1 hour, the mixture was warmed to room temperature. The reaction mixture was subjected to an aqueous work-up and the product extracted with chloroform. The organic solution was concentrated onto silica gel and the product was eluted (flash: 97:3 hexane:ether then prep-HPLC: Phenomenex Luna column (Si02), 10 micron, 250×50 mm, 150 mL/minute; 3:7 hexanes:dichloromethane) to give first eluting fraction: 5-bromo-N- (2,2,2-trichloro-1 -(4-ethylcyclohexylamino)ethyl)picolinamide (Compound-46, 106 mg) 1H NMR (300 MHz, CDCI3): delta = 8.64 (dd, J = 2.1 , 0.6 Hz, 1 H), 8.26 (d, J = 9.9 Hz, 1 H), 8.1 1 (dd, J = 8.4, 0.6 Hz, 1 H), 8.01 (dd, J = 8.4, 2.4 Hz, 1 H), 5.56 (t, J = 9.3 Hz, 1 H), 2.96 (brs, 1 H), 1 .80-1 .71 (m, 2H), 1 .59-1 .21 (m, 10H), 0.85 (t, J = 7.2 Hz, 3H), and second eluting fraction: 5-bromo-N-(2,2,2-trichloro-1 -(4- ethylcyclohexylamino)ethyl)picolinamide (Compound-47, 166 mg) 1H NMR (300 MHz, CDCI3): delta = 8.64 (dd, J = 2.1 , 0.6 Hz, 1 H), 8.30 (d, J = 9.9 Hz, 1 H), 8.1 1 (dd, J = 8.4, 0.9 Hz, 1 H),8.01 (dd, J = 8.4, 2.1 Hz, 1 H), 5.50 (t, J = 8.7 Hz, 1 H), 2.68-2.58 (m, 1 H), 2.16-2.07 (m, 1 H), 1 .86-1 .70 (m, 4H), 1 .27-1 .01 (m, 6H), 0.96-.087 (m, 1 H) 0.83 (t, J = 7.5 Hz, 3H).

The synthetic route of 90145-48-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALLERGAN, INC.; GARST, Michael E.; CHOW, Ken; HEIDELBAUGH, Todd M.; NGUYEN, Phong; WO2011/28927; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 6945-67-1, 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. 6945-67-1, name is 2-Bromo-4-nitropyridine. A new synthetic method of this compound is introduced below.

The 2-bromo-4-nitropyridine (1.00g, 4.93mmol),3-acetonitrile cyclobutylamine hydrochloride(759.30mg, 6.40mmol) and cesium carbonate (4.82g, 14.78mmol) were placed in the reaction flask,50mL 1,4-dioxane was added, and the reaction was carried out at 100C overnight.After LC-MS detection, the reaction was completed, cooled to room temperature, filtered to obtain a filtrate, concentrated under reduced pressure, and purified by column chromatography to obtain the title compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6945-67-1, 2-Bromo-4-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; Nanjing Shenghe Pharmaceutical Co., Ltd.; Wang Yong; Zhao Liwen; Wang Yazhou; Quan Xu; Liu Haixuan; Wang Xiaowei; Zhang Yan; Li Xue; Cao Chen; Guo Zhuang; Lv Kunzhi; Wang Hai; Zheng Guochuang; (126 pag.)CN111196804; (2020); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1352625-30-9, 3-Bromo-6-fluoropyrazolo[1,5-a]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, category: pyridine-derivatives, blongs to pyridine-derivatives compound. category: pyridine-derivatives

c) 6-Fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazolo[1,5-a]pyridine A mixture of 3-bromo-6-fluoropyrazolo[1,5-a]pyridine (Preparation 103b, 0.300 g, 1.4 mmol), potassium acetate (0.492 g, 5.0 mmol) and bis(pinacolato)diboron (2.77 g, 10.9 mmol) in 1,4-dioxane (5 mL) contained in a Schlenck vessel was submitted to three vacuum-argon cycles and tetrakis(triphenylphosphine)palladium(0) (0.380 g, 0.33 mmol) was then added. The mixture was further submitted to three vacuum-argon cycles, sealed and then was stirred and heated to 100 C. After 20 hours, the reaction mixture was cooled, evaporated and then taken up in pentane and filtered through diatomaceous earth (Celite) and the filter cake was washed with a mixture of ethyl acetate/ether (3:2). The combined filtrate and washings were evaporated and the residue was purified by reverse phase chromatography (C-18 silica from Waters, water/acetonitrile/methanol as eluents [0.1% v/v formic acid buffered] 0% to 100%) to give the title compound (0.130 g, 36%) as a yellow solid. LRMS (m/z): 263 (M+1)+.1H NMR (300 MHz, CDCl3) delta ppm (two sets of peaks are seen in the NMR due to the presence of both the boronate and boronic acid): NMR of boronate: 1.21 (s, 12H), 7.56 (m, 1H), 8.02 (m, 1H), 8.36 (s, 1H), 9.16 (m, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1352625-30-9, 3-Bromo-6-fluoropyrazolo[1,5-a]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; Almirall, S.A.; EP2397482; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 886365-48-6, 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 886365-48-6, name is 5-Bromo-2-(pyrrolidin-2-yl)pyridine. This compound has unique chemical properties. The synthetic route is as follows.

Step 1 Preparation of 2-(5-Bromo-pyridin-2-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester A solution of 5-Bromo-2-pyrrolidin-2-yl-pyridine (611 mg, 2.69 mmol) (previously described in WO200853319) in CH2Cl2 (20 ml) is treated with di-tert-butyl dicarbonate (881 mg, 4.04 mmol) and triethylamine (0.562 ml, 4.04 mmol), and stirred at ambient temperature for 16 hours. The reaction mixture is washed with 10percent aqueous citric acid solution (25 ml). The organic phase is concentrated on to silica gel (5 g) and purified by column chromatography (40 g silica gel, ethyl acetate/heptane 0-50percent) to afford the title compound (500 mg): 1H NMR (400 MHz, CDCl3) 1.23 (s, 5H), 1.4 5 (s, 4H), 1.82-2.09 (m, 3H), 2.24-2.43 (m, 1H), 3.47-3.74 (m, 2H), 4.67-4.99 (m, 1H), 7.05-7.14 (m, 1H), 7.71-7.78 (m, 1H), 8.59 (dd, 1H). m/z M+H 327.

According to the analysis of related databases, 886365-48-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Curtis, Michael; Duclos, Brian A.; Ewin, Richard A.; Johnson, Paul D.; Johnson, Timothy Allen; Vairagoundar, Rajendran; Billen, Denis; Goodwin, Richard M.; Haber-Stuk, Andrea K.; Kyne, Graham M.; Sheehan, Susan M. K.; US2013/237502; (2013); 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.603311-76-8, name is Ethyl 2-(6-bromoimidazo[1,2-a]pyridin-3-yl)acetate, molecular formula is C11H11BrN2O2, molecular weight is 283.12, as common compound, the synthetic route is as follows.Recommanded Product: Ethyl 2-(6-bromoimidazo[1,2-a]pyridin-3-yl)acetate

General procedure: To a 5 mL Schlenk tube were added aryl / heteroaryl acetates 3 (1.0 mmol, 1.0 equiv.), vinyl diphenylsulfonium triflate (434.4 mg, 1.2 mmol, 1.2 equiv.) and DMSO (5 mL). The mixture was stirred at room temperature for 2 min and to the mixture was added DBU (456 mg, 3 mmol, 3.0 equiv.). The mixture was stirred for 12 hours at room temperature till the reaction was complete. To the resulting mixture was added saturated ammonium chloride solution (25 mL), and the mixture was then extracted with EtOAc (3 x 150 mL). The combined organic layers were washed with H2O (2 x 30 mL), dried with anhydrous sodium sulfate. After concentration, product 4 was purified using column chromatography on silica gel using an appropriate eluent.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,603311-76-8, Ethyl 2-(6-bromoimidazo[1,2-a]pyridin-3-yl)acetate, and friends who are interested can also refer to it.

Reference:
Article; Zhou, Mingwei; Hu, Yimin; En, Ke; Tan, Xuefei; Shen, Hong C.; Qian, Xuhong; Tetrahedron Letters; vol. 59; 14; (2018); p. 1443 – 1445;,
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. 886365-46-4, name is 5-Chloro-3-methylpyridine-2-carboxylic acid. A new synthetic method of this compound is introduced below., Application In Synthesis of 5-Chloro-3-methylpyridine-2-carboxylic acid

To a solution of tert-butyl ((3aS,4R,8R)-4-(6-amino-3-fluoropyridin-2-yl)-4,7,7- trimethyl-8-oxido-3,3a,4,7-tetrahydro-2H-isothiazolo[l,5-a][l,4]thiazin-6-yl)carbamate (Int- 39AB, 150 mg, 0.35 mmol) in THF (20 mL) was added 5-chloro-3-methylpicolinic acid (92.8 mg, 0.53 mmol), followed by T3P (1.1 g, 1.75 mmol, 50% in ethyl acetate), and diisopropylethylamine (267 mg, 2.1 mmol). The reaction was stirred at 70 C for 4 h. After that, the reaction mixture was diluted with aqueous saturated sodium hydrogencarbonate solution (20 mL) and extracted with ethyl acetate (3 x 30 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated to give a crude product. The crude was purified by preparative TLC (silica gel, dichloromethane / ethyl acetate 1: 1, UV) to yield, after drying in vacuo, the title compound as a yellow solid (100 mg, 50% yield). MS (ES+) m/z 579.2 [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, 886365-46-4, 5-Chloro-3-methylpyridine-2-carboxylic acid.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BARTELS, Bjoern; CUENI, Philipp; DOLENTE, Cosimo; GUBA, Wolfgang; HAAP, Wolfgang; KUGLSTATTER, Andreas; OBST SANDER, Ulrike; PETERS, Jens-Uwe; ROGERS-EVANS, Mark; VIFIAN, Walter; WOLTERING, Thomas; (231 pag.)WO2016/55496; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 131747-62-1, 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.131747-62-1, name is 3-(Trifluoromethyl)pyridine-2-carboxaldehyde, molecular formula is C7H4F3NO, molecular weight is 175.108, as common compound, the synthetic route is as follows.

A solution of 2-([1,1?-biphenyl]-4-yl)-2,8-diazaspiro[4.5]decan-1-one 8 (TFA salt, 30 mg, 0.071 mmol) and 3-(trifluoromethyl)picolinaldehyde (18.74 mg, 0.107 mmol) in DCM (3 mL) and DMF (1 mL) was stirred at room temperature for 30 min. Sodium triacetoxyborohydride (22.7 mg, 0.11 mmol) was then added. The reaction mixture was stirred at room temperature for overnight. The reaction was quenched with water (0.2 mL) and the reaction mixture was extracted with DCM (20 mL). The organic fraction was separated and dried over anhydrous sodium sulfate. The dried solution was filtered and the filtrate was concentrated. The residue was purified by MDAP to afford compound 4h (13.5 mg, 33%) as a TFA salt. 1H NMR (400 MHz, DMSO-d6) delta ppm 1.82 (d, J= 13.80 Hz, 2H), 2.17-2.29 (m, 4H), 3.27-3.45 (m, 2H), 3.51-3.59 (m, 2H), 3.90 (t, J= 6.53 Hz, 2H), 4.80 (s, 2H), 7.31-7.39 (m, 1H), 7.46 (t, J= 7.53 Hz, 2H), 7.63-7.77 (m, 5 H), 7.77-7.85 (m, 2H), 8.36 (d, J= 8.28 Hz, 1H), 9.00 (d, J= 4.27 Hz, 1H), 10.07 (br s, 1H). 13C NMR (100MHz, DMSO-d6) delta ppm 153.0, 139.8, 139.2, 136.3, 129.5, 127.8, 127.3, 126.8, 124.4, 120.3, 49.8, 45.0, 43.6, 29.4, 27.6. HRMS C27H27F3N3O (M+H)+ calcd 466.2106, found: 466.2112. LC/MS: tR= 2.94 min, 99.9%, m/z: 466.0 (M+H)+.

Statistics shows that 131747-62-1 is playing an increasingly important role. we look forward to future research findings about 3-(Trifluoromethyl)pyridine-2-carboxaldehyde.

Reference:
Article; Deng, Guanghui; Zhao, Baowei; Ma, Yingli; Xu, Qiongfeng; Wang, Hailong; Yang, Liuqing; Zhang, Qing; Guo, Taylor B.; Zhang, Wei; Jiao, Yang; Cai, Xin; Zhang, Jinqiang; Liu, Houfu; Guan, Xiaoming; Lu, Hongtao; Xiang, Jianing; Elliott, John D.; Lin, Xichen; Ren, Feng; Bioorganic and Medicinal Chemistry; vol. 21; 21; (2013); p. 6349 – 6358;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem