Pyridine-derivatives

Synthetic Route of 113209-90-8 ,Some common heterocyclic compound, 113209-90-8, molecular formula is C6H5ClFNO, 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′-[3-(dimethylamino)-1-pyrrolidinyl]-4-hydroxy-2/-/-1 ,3′-bipyridin-2-one (150 mg, 0.499 mmol) and triphenylphosphine (327 mg, 1.249 mmol) was treated with (4-chloro-5-fluoro-2-pyridinyl)methanol (81 mg, 0.499 mmol) dissolved in dichloromethane (5 ml). Bis(1 ,1-dimethylethyl) (E)-1 ,2-diazenedicarboxylate (287 mg, 1.249 mmol) was added in two portions, and the reaction mixture was stirred at 250C for 2 h then concentrated under a stream of nitrogen gas. Purification by reverse phase HPLC (1 to 50% gradient) and concentration of the fractions containing product provided a residue. The residue was treated with aqueous NaHCO3 solution and extracted with ethyl acetate. The organic layer was washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to provide the title compound as a white solid (1 14 mg, 51 %): 1H NMR (400 MHz, CDCI3) delta ppm 8.46 (s, 1 H), 8.06 (d, J = 2.7 Hz, 1 H), 7.56-7.48 (m, 2 H), 7.21 (d, J = 7.6 Hz, 1 H), 6.43 (d, J = 9.0 Hz, 1 H), 6.09 (dd, J = 7.4, 2.5 Hz, 1 H), 5.98 (d, J = 2.7 Hz, 1 H), 5.10 (s, 2 H), 3.95-3.84 (m, 1 H), 3.77-3.65 (br m, 2H), 3.55-3.22 (br m, 2 H), 2.60 (br s, 6 H), 2.47-2.29 (br m, 2 H); ES-LCMS m/z 444 {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,113209-90-8, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/76387; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 144657-66-9, tert-Butyl 3-formyl-1H-pyrrolo[2,3-b]pyridine-1-carboxylate, 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, Quality Control of tert-Butyl 3-formyl-1H-pyrrolo[2,3-b]pyridine-1-carboxylate, blongs to pyridine-derivatives compound. Quality Control of tert-Butyl 3-formyl-1H-pyrrolo[2,3-b]pyridine-1-carboxylate

General procedure: To a solution of 3-benzyl-5-(2-hydroxyethyl)-4-methylthiazol-3-ium chloride in ethanol was added triethylamine and the mixture was stirred at 70 C for 5 min. To the resulting yellow solution were added an aldehyde and a solution of an imine in ethanol. The reaction mixture was stirred in a sealed tube at 50 – 70 C for 18 – 120 h. The reaction mixture was concentrated under reduced pressure and the crude material was purified by flash chromatography on silica gel or precipitation.

The synthetic route of 144657-66-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KATHOLIEKE UNIVERSITEIT LEUVEN; BARDIOT, Dorothee; CARLENS, Gunter; DALLMEIER, Kai; KAPTEIN, Suzanne; McNAUGHTON, Michael; MARCHAND, Arnaud; NEYTS, Johan; SMETS, Wim; WO2013/45516; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1149-24-2, 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. 1149-24-2, name is Diethyl 2,6-dimethylpyridine-3,5-dicarboxylate, molecular formula is C13H17NO4, 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.

General procedure: To a mixture of ethyl acetoacetate or methyl acetoacetate (1 eqv), formaldehyde (1.1 eqv) and NH4OAc (1.5 eqv) in acetic acid (3 mL) was added FeWO4 (20 mol%) at room temperature and the mixture was heated at 80 C for 2 h (monitoring by TLC) to give poly-substituted pyridine (3), to this solution isatin (1 eqv) was added and heating continued at same temperature for 3 h (monitoring by TLC). After that the reaction mixture was cooled to room temperature neutralized with sodium bicarbonate and extracted with EtOAc (2 × 10 mL). The organic layers were washed with brine, dried using sodium sulphate .Evaporation of the solvent gave the crude product which was purified by silica gel column chromatography. Elution of the column with petroleum ether-EtOAc gave the desired product.

According to the analysis of related databases, 1149-24-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Paplal, Banoth; Nagaraju, Sakkani; Sathish, Kota; Kashinath, Dhurke; Catalysis Communications; vol. 103; (2018); p. 110 – 115;,
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. 124236-37-9, name is Methyl 5-(trifluoromethyl)picolinate, molecular formula is C8H6F3NO2, 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: Methyl 5-(trifluoromethyl)picolinate

Step 2: (0564) To a mixture of methyl 5-(trifluoromethyl)pyridine-2-carboyxlate prepared above (0.2 g, 0.97 mmol) and (trifluoromethyl)trimethylsilane (0.173 g, 1.22 mmol) stirring at -78 C. in pentante (3 mL) under a nitrogen atmosphere was slowly added tetrabutylammonium fluoride (1.0 M in THF, 25 muL, 0.024 mmol). The reaction was allowed to come to room temperature and stirred overnight (total reaction time 16 hours). At that time, 2 N HCl was added, and the mixture was stirred vigorously at room temperature for 2 hours. The solution was extracted with DCM. The combined organic layers were dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (0-20% EtOAc/hexanes over 20 minutes) to provide the trifluoromethyl ketone product (0.084 g, 35%).

With the rapid development of chemical substances, we look forward to future research findings about 124236-37-9.

Reference:
Patent; MERCK SHARP & DOHME CORP.; Scott, Jack D.; Stamford, Andrew W.; Gilbert, Eric J.; Cumming, Jared N.; Iserloh, Ulrich; Misiaszek, Jeffrey A.; Li, Guoqing; US2015/307465; (2015); 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.823221-93-8, name is 5-Bromo-2-chloro-4-(trifluoromethyl)pyridine, molecular formula is C6H2BrClF3N, molecular weight is 260.44, as common compound, the synthetic route is as follows.Quality Control of 5-Bromo-2-chloro-4-(trifluoromethyl)pyridine

To a solution of 5-bromo-2-chloro-4-trifluoromethyl-pyridine (1.0 g, 3.84 mmol) in EtOH (5 mL) was added freshly prepared 1M solution of sodium ethanolate in EtOH (5.76 mL, 5.76 mmol) at RT and the resulting RM was heated to reflux for 2 h. The RM was concentrated under reduced pressure and subsequently diluted with CH2Cl2, washed with water and brine and dried. The solvent was evaporated under reduced pressure to yield the desired compound (700 mg, 67%) which was used in next step without further purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,823221-93-8, 5-Bromo-2-chloro-4-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; GRUeNENTHAL GMBH; VOSS, FELIX; NORDHOFF, SONJA; WACHTEN, SEBASTIAN; WELBERS, ANDRE; RITTER, STEFANIE; US2015/166505; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 623585-74-0, Adding some certain compound to certain chemical reactions, such as: 623585-74-0, name is Methyl 2,5-dichloroisonicotinate,molecular formula is C7H5Cl2NO2, 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 623585-74-0.

A mixture of 5-(tetramethyl- 1,3 ,2-dioxaborolan-2-yl)-2-(trifluoromethyl)pyrimidine (3 g, 10.95 mmol, 1.00 equiv), methyl 2,5-dichloropyridine-4-carboxylate (6 g, 29.12 mmol, 1.00 equiv), Pd(dppf)C12 (1.55 g, 2.12 mmol, 0.20 equiv), and potassium carbonate (8.78 g, 63.53 mmol, 5.80 equiv) in dioxane (100 mL)/water(5 mL) was stirred for 12 h at 60C under nitrogen. The reaction mixture was concentrated under vacuum. The residue purified by a silica gel column eluting with ethyl acetate/petroleum ether (1:10) to afford the title compound (1.4 g, 40%) as a white solid.

According to the analysis of related databases, 623585-74-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; CHEN, Huifen; CHU, Yanyan; DO, Steven; ESTRADA, Anthony; HU, Baihua; KOLESNIKOV, Aleksandr; LIN, Xingyu; LYSSIKATOS, Joseph P.; SHORE, Daniel; VERMA, Vishal; WANG, Lan; WU, Guosheng; YUEN, Po-wai; WO2015/52264; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 408365-87-7, 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.408365-87-7, name is Ethyl 2-(6-((tert-butoxycarbonyl)amino)pyridin-2-yl)acetate, molecular formula is C14H20N2O4, molecular weight is 280.32, as common compound, the synthetic route is as follows.

2C. (6-amino-pyridin-2-yl) acetic acid ethyl ester; To a solution of title compound 2B, (6-te;’t-butoxycarbonylamino-pyridin-2-yl) acetic acid ethyl ester, (1.38 g, 4.92 mmol) in DCM (20 ml) is added 4M HCl in dioxane (4 eq, 19.7 mmol) and the mixture is stirred for 4 h at room temperature. A further 4 eq of 4M HCl in dioxane are added and the mixture is left to stir for 16 h. The reaction mixture is concentrated in vacuo to give the title compound (1.20 g, > 100% ~14% starting material remained). LC/MS: 75% MH+, m/z 181, Rt = 0.68 mins. The product is used crude without further purification.

The chemical industry reduces the impact on the environment during synthesis 408365-87-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; EVOTEC AG; WO2006/50908; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 55404-31-4, Adding some certain compound to certain chemical reactions, such as: 55404-31-4, name is 3-Bromo-2-chloro-4-methylpyridine,molecular formula is C6H5BrClN, 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 55404-31-4.

(2) Synthesis of 3-bromo-2-methoxy-4-methylpyridine 3-bromo-2-chloro-4-methylpyridine (1 g) was added to DMF (5.6 mL). Sodium methoxide (28% solution in methanol, 4.6 mL) was added to the solution, and the mixture was stirred at 100 C. for 12 hours. The reaction mixture was partitioned by adding ethyl acetate and water. The organic layer was dried over anhydrous magnesium sulfate. The desiccant was removed by filtration, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 5% to 30%) to give the title compound (1.1 g). 1H-NMR (400 MHz, CDCl3) delta (ppm): 2.40 (s, 3H), 4.00 (s, 3H), 6.77 (d, J=5.1 Hz, 1H), 7.94 (d, Hz, 1H).

According to the analysis of related databases, 55404-31-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; EISAI R&D MANAGEMENT CO., LTD.; Norimine, Yoshihiko; Takeda, Kunitoshi; Hagiwara, Koji; Suzuki, Yuichi; Ishihara, Yuki; Sato, Nobuaki; US2013/143907; (2013); A1;,
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. 727356-19-6, name is 2-Bromo-6-(chloromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows. Formula: C6H5BrClN

Step 3; Preparation of 3-oxopiperazine-1-carboxyimidothionic acid 6-bromopyridin-2-ylmethyl ester 2-Bromo-6-chloromethylpyridine (1.50 g, 7.26 mmol) obtained in Step 1 was dissolved in ethanol (15 ml) and 3-oxopiperazine-1-carbothionic acid amide (1.16 g, 7.29 mmol) obtained in Step 2 was added, and the mixture was heated to reflux for 2 hours. After the reaction solution was cooled to room temperature, the solution obtained by vacuum concentration was neutralized with a saturated aqueous sodium bicarbonate, and the precipitated solid was separated by filtration, washed with water and the title compound (1.67 g, 70%) was obtained.

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, 727356-19-6, 2-Bromo-6-(chloromethyl)pyridine.

Reference:
Patent; JAPAN TOBACCO INC.; US2006/205731; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 112110-07-3, 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.112110-07-3, name is 5-(Trifluoromethyl)pyridin-3-amine, molecular formula is C6H5F3N2, molecular weight is 162.11, as common compound, the synthetic route is as follows.

1-(((Benzyloxy)carbonyl)amino) cyclopropane-1-carboxylic acid (50 mg, 0.21 mmol), 5-(trifluoromethyl)pyridin-3-amine (104 mg, 0.64 mmol), and DIPEA (111 muL, 0.64 mmol) were dissolved in DMF (1 mL), and then HATU (97 mg, 0.26 mmol) was added thereto, followed by stirring at room temperature overnight. A saturated aqueous sodium hydrogen carbonate solution was added to a reaction liquid, the mixture was stirred for a while, and then extraction was performed with ethyl acetate. A separated organic layer was washed with a saturated saline solution and dried over anhydrous sodium sulfate, an insoluble substance was filtered, and then a solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate) (concentration gradient: 40% to 60%) to obtain a crude product (white powders, 126 mg) of benzyl (1-((5-(trifluoromethyl)pyridin-3-yl)carbamoyl)cyclopropyl)carbamate.

The chemical industry reduces the impact on the environment during synthesis 112110-07-3, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Nippon Chemiphar Co., Ltd.; Kinki University; TANAKA Hiroto; OOI Isao; HAYASHIDA Kohei; OGAWA Toru; KAWABATA Atsufumi; (64 pag.)EP3572403; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem