Category: pyridine-derivatives

Electric Literature of 136592-00-2, 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 136592-00-2 as follows.

To a stirred solution of 2-chloro-1-(6-chloropyridin-3-yl)ethanone (1.85 g, 9.74 mmol) in toluene (30 ml) was added hexamethylenetetramine (1.36 g, 9.74 mmol). The mixture was stirred at 40 C. for 16 h. The resulting solid was filtered and washed with toluene and ether to afford a brown solid. The solid was added to ethanol (40 ml) and concentrated HCl (15 ml) and the mixture was stirred at room temperature for 20 h. Concentrate the mixture to afford, 2-amino-1-(6-chloropyridin-3-yl)ethanone hydrochloride as an orange solid (2.00 g, 99%): ESI-LRMS m/e calcd for C7H7ClN2O HCl [M+] 170, found 171 [M+H+] (free base)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,136592-00-2, its application will become more common.

Reference:
Patent; Alam, Muzaffar; Berthel, Steven Joseph; Brinkman, John A.; Hawley, Ronald Charles; Li, Hongju; Palmer, Wylie Solang; Pietranico-Cole, Sherrie; Sarabu, Ramakanth; Smith, Mark; So, Sung-Sau; Yi, Lin; Zhai, Yansheng; Zhang, Qiang; Zhao, Shu-Hai; US2012/230951; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 870997-85-6, 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. 870997-85-6, name is 3-Amino-5-bromopyridine-2-carboxylic Acid, molecular formula is C6H5BrN2O2, 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.

Step 1: 3-Amino-5-(4-trifluoromethyl-phenylsulfanyl)-pyridine-2-carboxylic acid: [00275] A solution of 3-amino-5-bromopyridine-2-carboxylic acid (Int 1, 3.78 g, 17.4 mmol), 4- trifluoromethyl-benzenethiol (CAS: 825-83-2, 4.1 g, 21 mmol) and DBU (2.60 mL, 17.4 mmol) was prepared in DMA (15 mL). This mixture was heated at 140 C for 45 minutes in a microwave reactor. Next, the mixture was diluted with a mixture of 1% AcOH in water. A suspension was obtained that was subsequently filtered. The collected solid was washed with a 1% AcOH/water mixture followed by washing with petroleum ether. After drying in a vacuum oven, a powder was obtained that was used without additional purification.

According to the analysis of related databases, 870997-85-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ABBVIE S.A.R.L.; GALAPAGOS NV; ALTENBACH, Robert, J.; COWART, Marlon, D.; DE MUNCK, Tom, Roger Lisette; DROPSIT MONTOVERT, Sebastien Jean, Jacques Cedric; GFESSER, Gregory, A.; KELGTERMANS, Hans; MARTINA, Sebastien, Laurent Xavier; VAN DER PLAS, Steven, Emiel; WANG, Xueqing; (300 pag.)WO2016/193812; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 65370-42-5, 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 65370-42-5, name is 4-Chloro-2-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows.

Compound 8 (4g, 0.03mol) was added to a 100mL eggplant-shaped bottle, NMP 30mL was added, stirred, and added sequentially Diisopropylethylamine (10 g, 0.08 mol), compound 9 (4.8 g, 0.03 mol), then reacted at 150 C for 24 h, using thin layer chromatography(TLC) followed the reaction. After 24 h, TLC showed the end of the reaction. Part of the solvent was evaporated under reduced pressure. After suction filtration, drying and recrystallization, 3.20 g of a gray solid compound 10 was obtained in a yield of 50%.

According to the analysis of related databases, 65370-42-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai University of Engineering Science; Yin Lingfeng; Mao Yongjun; Zhao Zhiwei; Bu Lehao; Wu Pengfei; Wang Han; (12 pag.)CN109942576; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 84539-30-0, name is 5-Bromo-N-methylpyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows. Formula: C6H7BrN2

a) tert-butyl 5-methoxy-2-[6-(methylamino)pyridin-3-yl]-lH-indole-l-carboxylate l-(tert-Butoxycarbonyl)-5-methoxyindole-2-boronic acid (2 mmol), 5-bromopyridine-2- methylamine (2 mmol), Pd(dppf)Cl2 (0.10 mmol) and 2M Na2CO3 (aq.) (3 mL) were mixed in THF/water 5:1 (10 mL) in a 20 mL microwave vial. The reaction mixture was stirred at 1200C in the microwave reactor for 15 min. Water was added and the solution was extracted with EtOAc. The organic extracts were dried over Na2SO4, filtered and concentrated. The crude mixture was purified by flash chromatography (Heptane/EtOAc gradient) to afford the title intermediate (256 mg). 1H NMR delta ppm 8.04 (d, 1 H) 7.94 (d, 1 H) 7.43 (dd, 1 H) 7.08 (d, 1 H) 6.89 (dd, 1 H) 6.64 (d, 1 H) 6.53 (s, 1 H) 6.50 (d, 1 H) 3.78 (s, 3 H) 2.80 (d, 3 H) 1.36 (s, 9 H); MS m/z (M+H) 354.

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, 84539-30-0, 5-Bromo-N-methylpyridin-2-amine.

Reference:
Patent; ASTRAZENECA AB; WO2008/108729; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 58584-92-2, 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. 58584-92-2, name is 2-Amino-6-chloronicotinic acid. A new synthetic method of this compound is introduced below.

To a solution of 2-amino-6-chloronicotinic acid (1.0 g, 5.79 mmol), HOBT (932 mg, 6.95 mmol) and EDCI (2.22 g, 11.6 mmol) in 15 mL of DMF was added triethylamine (5.86 g, 57.9mmol) and NH4C1 (1.55 g, 28.9 mmol). Then the mixture was stirred at room temperature for 16 h. The solution was concentrated in vacuo to remove DMF and the residue was suspended in saturated NaHCO3. Finally the 2-amino-6-chloronicotinamide (800 mg, yield: 81%) was obtained by filtration without further purification. ?H-NMR (DMSO-d6, 400 MHz) 7.95 (d, J = 8.4 Hz, 1H), 7.62 (s, 2H), 7.39 (s, 2H), 6.59 (d, J = 8.4 Hz, 1H). MS (M+H): 172 / 174.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,58584-92-2, 2-Amino-6-chloronicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DAI, Xing; LIU, Hong; PALANI, Anandan; HE, Shuwen; NARGUND, Ravi; XIAO, Dong; ZORN, Nicolas; DANG, Qun; MCCOMAS, Casey C.; PENG, Xuanjia; LI, Peng; SOLL, Richard; WO2014/205593; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 630120-99-9, 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. 630120-99-9, name is 5-(Benzyloxy)-2-bromopyridine. A new synthetic method of this compound is introduced below.

1-(5-Benzyloxy-pyridin-2-yl)-ethanone A mixture of 5-benzyloxy-2-bromo-pyridine (1.0 g), N-methoxy-N-methyl-acetamide (780 mg) and THF (20 mL) under argon at -60 C. was added n-BuLi (2.6 M in toluene, 2.9 mL). After 1 hour the cooling bath was removed. After reaching room temperature the mixture was quenched by addition of saturated NH4Cl-solution. The mixture was distributed between EA and brine. The organic phase was dried (Na2SO4), filtered and concentrated. The residue was purified by chromatography (silica gel, heptane to EA/heptane 3:7) to provide the subtitle compound. MS ESI+: m/z=228 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,630120-99-9, 5-(Benzyloxy)-2-bromopyridine, and friends who are interested can also refer to it.

Reference:
Patent; SANOFI; SCHWINK, Lothar; BOSSART, Martin; GLOMBIK, Heiner; GOSSEL, Matthias; KADEREIT, Dieter; KLABUNDE, Thomas; MAIER, Thomas; STENGELIN, Siegfried; US2014/99333; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 67515-76-8, Methyl 5-aminopicolinate, 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

N-Bromosuccinimide (468 mg, 2.63 mmol) was added portion-wise to a 50 o solution of methyl 5-aminopyridine-2-carboxylate (400 mg, 2.6 mmol) in acetonitrile (15 mL), and the reaction mixture was heated at 50 00 overnight. Crude reaction mixtures from six additional small-scale reactions of this transformation were added (total starting material quantity: 760 mg, 5.0 mmol), and the resulting mixture was concentrated invacuo, then purified via silica gel chromatography (Gradient: 2% to 66% ethyl acetate in petroleum ether), providing the product as a red solid. Yield: 150 mg, 0.65 mmol, 13%. 1H NMR (400 MHz, CDCI3) oe 8.23 (5, 1H), 8.16 (5, 1H), 4.61 (brs, 2H), 3.97 (5, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,67515-76-8, Methyl 5-aminopicolinate, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER INC.; BRODNEY, Michael Aaron; DAVOREN, Jennifer Elizabeth; GARNSEY, Michelle Renee; ZHANG, Lei; O’NEIL, Steven Victor; (174 pag.)WO2016/9297; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 155377-05-2, 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 155377-05-2 as follows.

The biuret (13 g, 126.3 mmol) was dissolved in 300 mL of ethylene glycol dimethyl ether, sodium hydride (42 g, 1053 mmol) was added portionwise, and stirred at 50 C for 1 h. Methyl 6-(trifluoromethyl)-picolinate (21.6 g, 105.3 mmol) was added and the mixture was heated at 85 C for 16 h. The reaction solution was poured into water, the pH was adjusted with concentrated hydrochloric acid, filtered, and then filtered to give the title compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,155377-05-2, its application will become more common.

Reference:
Patent; Nanjing Shenghe Pharmaceutical Co., Ltd.; Zhao Liwen; Zhang Jin; Chen Cheng; Xu Chenglong; Wang Cheng; (44 pag.)CN110054614; (2019); A;,
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. 183610-70-0, name is 2-Amino-3-(trifluoromethyl)pyridine, molecular formula is C6H5F3N2, 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. Recommanded Product: 2-Amino-3-(trifluoromethyl)pyridine

A mixture of 3-(trifluoromethyl)pyridin-2-amine (3.00 g, 18.5 mmol), 1- bromobutan-2-one (3.76 g, 24.9 mmol), sodium hydrogencarbonate (3.11 g, 37.0 mmol) and sodium iodide (0.832 g, 5.55 mmol) in ethanol (37 mL) was refluxed overnight. The ethanol was removed in vacuo and the resulting material was treated with water and extracted with ethyl acetate. The combined organics were dried over MgSO4 and concentrated. The product was chromatographed using a 0:100 to 50:50 E:H gradient to afford the title compound as a white solid (2.92, 74%). MS (ES) m/z 215.1

With the rapid development of chemical substances, we look forward to future research findings about 183610-70-0.

Reference:
Patent; WYETH; WO2009/86123; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 102830-75-1, 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 102830-75-1, name is 3-Bromo-5-chloro-2-methoxypyridine. This compound has unique chemical properties. The synthetic route is as follows.

iNTERMEDIATE 16 (4S,5R)-5- 13 ,5-Bis(trifluoromethyl)phenyl] -3- 15-(5-chloro-2-methoxypyridin-3 -yl)-2-(methylthio?)pyrimidin-4-yl]methyH -4-methyl- 1,3 -oxazolidin-2-oneA dioxane (17.3 mL) solution of (4S,5R)-5- [3 ,5-bis(trifluoromethyl)phenyl] -4-methyl-3 – { [2- (methylsulfanyl)-5-(4,4,5,5-tetramethyl- 1,3 ,2-dioxaborolan-2-yl)pyrimidin-4-yl]methyl} -1,3 – oxazolidin-2-one (II?1TERMEDIATE 21, 2.0 g, 3.46 mmol), 3-bromo-5-chloro-2- methoxypyridine (0.925 g, 4.16 mmol) and 2M potassium phosphate tribasic (3.5 mL, 7.00mmol) in a microwave vial was evacuated and charged three times with nitrogen. Then Pd(Ph3P)4 (0.400 g, 0.346 mmol) was added and the reaction vial was capped. The reaction was stirred for 10 minutes at 170C in a microwave reactor. LCMS showed complete conversion to the product. The reaction was diluted with acetonitrile (5 mL) and filtered through a 2g plug of RP C18 silica, rinsing with 10 mL acetonitrile. The filtrate was concentrated and the crude waspurified by silica gel chromatography, eluting with a gradient of 0-50% ethyl acetate/hexanes to give the title compound as a pale yellow foam. LCMS (M+H)*: 593.3

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 102830-75-1, 3-Bromo-5-chloro-2-methoxypyridine.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ACTON, John, J., III; YE, Feng; VACHAL, Petr; SHA, Deyou; DROPINSKI, James, F.; CHU, Lin; ONDEYKA, Debra; KIM, Alexander, J.; COLANDREA, Vincent, J.; ZANG, Yi; ZHANG, Fengqi; DONG, Guizhen; WO2013/165854; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem