Category: pyridine-derivatives

766-11-0, A common compound: 766-11-0, name is 5-Bromo-2-fluoropyridine,molecular formula is C5H3BrFN, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Preparation of 3-Methyl-5-(4,4,5,5-tetramethyl-[1 ,3,2]dioxaborolan-2-yl)-1 H-pyrazolo[3,4-b]pyridine (79) 7475 76 77Step 1 :7475To a stirred solution of diisopropyl-amine (50 g, 0.5 mol) in dry THF (1000 mL) was added dropwise n- BuLi (200 mL, 0.5 mol) at -780C under N2 atmosphere. After the addition, the resulting mixture was allowed to warm up to O0C, maintained for 10 minutes and cooled to -780C again. A mixture of compound 74 (80 g, 0.455 mol) in THF (1000 mL) was added dropwise to the LDA solution at -780C under N2 atmosphere. After the addition, the reaction mixture was stirred at -780C for 30 minutes. Then formic acid ethyl ester (50 g, 0.68 mol) was added portionwise to the mixture at -780C. After 2 minutes, the resulting mixture was quenched with a solution of 10% citric acid in THF (400 mL) at -780C. The mixture was allowed to warmed up to room temperature and poured into H2O (500 mL), extracted with EtOAc (500 mL x 3). The combined organic layers were washed with brine (500 mL), dried over Na2SO4 and concentrated in vacuo to give compound 75 (92 g, 99%) as a yellow solid.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 766-11-0.

Reference:
Patent; PFIZER INC.; WO2009/16460; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 5470-70-2, Methyl 6-methylnicotinate, 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, 5470-70-2, blongs to pyridine-derivatives compound. 5470-70-2

To a solution of methyl 6-methylnicotinate (25 g, 0.16 mol) in ethyl ether (620 mL) under nitrogen was added dropwise sodium bis(2-methoxyethoxy)aluminium hydride (Red-Al.(R).) (65wt.percent in toluene, 110 mL, 0.37 mol) at room temperature. The mixture was then heated to reflux for 1.5 hr. After cooling, the reaction mixture was quenched with water (500 mL) at 0 0C and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over anhydrous MgSO4, filtered, and concentrated. The residue was purified by silica gel column to afford the title compound.

With the rapid development of chemical substances, we look forward to future research findings about 5470-70-2.

Reference:
Patent; RENOVIS, INC.; WO2009/110985; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

55589-47-4, 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.55589-47-4, name is 3-Methylpicolinaldehyde, molecular formula is C7H7NO, molecular weight is 121.14, as common compound, the synthetic route is as follows.

To a solution of X4-012-3 (4.0 g, 21.5 mmol), L-proline (1.0 g, 8.7 mmol) and 3-methylpicolinaldehyde (3.4 g, 28.0 mmol) in MeOH (200.0 mL) was added aq. methanamine (6 mL, 40percent). The solution was stirred at room temperature overnight. The solvent was removed under reduced pressure and purified by column chromatography to give X4-012-4 (4.1 g, 59.6 percent yield) as an orange solid. The structure was confirmed by H-HNOESY. LCMS (Agilent LCMS 1200-6120, Column: Waters X-Bridge C18 (50 mm*4.6 mm*3.5 iim); Column Temperature: 40 ¡ãC; Flow Rate: 2.0 mL/min; Mobile Phase: from 90percent [(total 10 mM AcONH4) water/CH3CN = 9/1 (v/v)] and 10percent [(total 10 mM AcONH4) water/CH3CN = 1/9 (v/v)] to 10percent [(total 10 mM AcONH4) water/CH3CN = 9/1 (v/v)] and 90percent [(total 10 mM AcONH4) water/CH3CN = 1/9 (v/v)] over 1.6 mm, then held under this condition for 2.4 mm, finally changed to 90percent [(total 10 mM AcONH4) water/CH3CN = 9/1 (v/v)] and 10percent [(total 10 mM AcONH4) water/CH3CN = 1/9 (v/v)] over 0.1 mm and held under this condition for 0.7 mi. Purity: 74.83 percent. Rt = 1.49 mm; MS Calcd.: 320.1; MS Found: 321.2 [M + H], MS Found:353.3 [M+MeOH].

Statistics shows that 55589-47-4 is playing an increasingly important role. we look forward to future research findings about 3-Methylpicolinaldehyde.

Reference:
Patent; X4 PHARMACEUTICALS, INC.; BOURQUE, Elyse Marie Josee; SKERLJ, Renato; (279 pag.)WO2017/223229; (2017); A1;,
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. 5398-44-7, name is 2,6-Dichloroisonicotinic acid. A new synthetic method of this compound is introduced below., 5398-44-7

To a solution of 2,6-dichloroisonicotinic acid (2 g, 10.4 mmol) in toluene (50 mL) N,N dimethylformamide di-tert-butil acetal (15 mL, 62.5 mmol) was added under nitrogen atmosphere and mixture heated at 80 Ethyl acetate was added and organic layer was washed with water and brine, dried (MgSO4), filtered and concentrated to yield the title compound (2.34 g, 87%) as a solid.LRMS (m/z): 249 (M+1)+.1H NMR (400 MHz, CHLOROFORM-d) ppm 1.60 (s, 9 H) 7.74 (s, 2 H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5398-44-7, 2,6-Dichloroisonicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; Almirall, S.A.; Vidal Juan, Bernat; Forns Berenguel, Maria Pilar; Castillo Mcquade, Marcos; Erra Sola, Montserrat; Mir Cepeda, Marta; EP2441755; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Some common heterocyclic compound, 16063-70-0, molecular formula is C5H2Cl3N, 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.16063-70-0

400 g of sulfolane and 400 g of dimethylsulfoxide were weighed into a 1000 mL flask and dehydrated to a temperature of less than 0.05% at 200 C under a pressure of 0.07 MPa (negative pressure)96 g (1.66 mol) of cesium fluoride, 96 g (1.66 mol) of potassium fluoride, 120 g (0.67 mol) of trichloropyridine, 2 g of 18-crown ether and 3 g of potassium carbonate were weighed into a reaction flask at 120 C and heated to 200 C The product was collected in about 3 hours. 95 g (0.51 mol) of the product was obtained in 90% yield. The purity was 96.8% as determined by gas chromatography.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 16063-70-0.

Reference:
Patent; Weixun Chemical (Nanjing) Co., Ltd; Wang, Faqiang; (4 pag.)CN106008329; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 145100-50-1, 1,1,1-Trifluoro-N-(pyridin-2-yl)-N-((trifluoromethyl)sulfonyl)methanesulfonamide, 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, 145100-50-1, blongs to pyridine-derivatives compound. 145100-50-1

General procedure: Either (2S)-13 or (2R)-13 was dissolved in anhydrous DCM, and1.5 equivalents of 2-Pyridyltriflimide were added. The flask was placedunder N2 atmosphere and cooled to -78 C. 3.0 equivalents of N,Ndiisopropylethylaminewere added and the reaction slowly warmed toroom temperature and stirred for 20 h. Saturated aqueous ammoniumchloride was added, and extraction done with DCM. Organic fractionswere dried over sodium sulfate and purification was done by flashchromatography 98:2 (DCM:MeOH). TLC eluents used (95:5Dichloromethane: MeOH).

With the rapid development of chemical substances, we look forward to future research findings about 145100-50-1.

Reference:
Article; Perry, Charles K.; Casey, Austen B.; Felsing, Daniel E.; Vemula, Rajender; Zaka, Mehreen; Herrington, Noah B.; Cui, Meng; Kellogg, Glen E.; Canal, Clinton E.; Booth, Raymond G.; Bioorganic and Medicinal Chemistry; vol. 28; 3; (2020);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

69045-84-7 ,Some common heterocyclic compound, 69045-84-7, molecular formula is C6H2Cl2F3N, 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.

500mL glass bottle,Supporting serpentine condenser,54.0 g (0.25 mol) of 2,3-dichloro-5-trifluoromethylpyridine,DMAC 150g,Anhydrous KF 18.9 g (0.325 mol),4 g (0.018 mol) of benzyltriethylammonium chloride,The temperature of the oil bath was raised to 170 C,Time reaction 5h,After DMAC was recovered by distillation,2-Fluoro-3-chloro-5-trifluoromethylpyridine was collected under reduced pressure48.6g,Its content of 2-fluoro-3-chloro-5-trifluoromethylpyridine was 99.5%Yield 97%.

According to the analysis of related databases, 69045-84-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Inner Mongolia Jiaruimi Fine Chemical Co., Ltd.; Dong Yongxia; Xiang Bin; Li Jun; (5 pag.)CN107286087; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

586-95-8, 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. 586-95-8, name is 4-Pyridinemethanol. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A solution of catalyst 1 (2 mol %, 0.01 mmol), acetophenone (1.0 mmol), benzyl alcohol (1.2 mmol), cesium carbonate (1.5 mmol), and xylene (3 mL) were stirred in a Schlenk tube in N2 atmosphere. The mixture was heated under reflux for 24 h and then cooled to room temperature. The resulting solution was directly purified by column chromatography with petroleum ether/ethyl acetate (10 : 1) as eluent to give the desired product.

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, 586-95-8, 4-Pyridinemethanol.

Reference:
Article; Yu; Wang; Wu; Wang; Russian Journal of General Chemistry; vol. 86; 1; (2016); p. 178 – 183; Zh. Obshch. Khim.;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

69045-84-7, Adding a certain compound to certain chemical reactions, such as: 69045-84-7, 2,3-Dichloro-5-(trifluoromethyl)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, 69045-84-7, blongs to pyridine-derivatives compound.

Step A Synthesis of 3-chloro-5-trifluoromethylpyrid-2-ylhydrazine To a solution of 60 mL of hydrazine monohydrate in 380 mL of ethanol was added 81 g (0.38 mole) of 2,3-dichloro-5-trifluoromethylpyridine during a period of 25 minutes. At the end of the addition the temperature had risen to 37 C. This mixture was heated to reflux and maintained at reflux for approximately 15 hours. The solvent was evaporated under reduced pressure, leaving a wet slurry that was immediately recrystallized from boiling ethanol/water (5:2). The mixture was cooled to 20 C. and then filtered. The filter cake was air-dried, yielding approximately 60 g of 3-chloro-5-trifluoromethylpyrid-2-ylhydrazine. The NMR spectrum was consistent with the assigned structure. This reaction was repeated to obtain additional material for subsequent reactions.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,69045-84-7, its application will become more common.

Reference:
Patent; FMC Corporation; US5321002; (1994); A;,
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. 6419-36-9, name is 2-(Pyridin-3-yl)acetic acid hydrochloride. A new synthetic method of this compound is introduced below., 6419-36-9

Example C2 Synthesis of 3-pyridyl-1-hydroxyethylidene-1,1-bisphosphonic Acid In a 100 ml rounded bottom, three necked flask equipped with a magnetic stirrer, a thermometer, a reflux condenser and a compensated-pressure dropping funnel were charged: 1.00 g (5.76¡¤10-3 mol) of 3-pyridyl acetic acid hydrochloride, 1.46 g (1.78¡¤10-2 mol) of phosphonic acid, 3.01 g (1.72¡¤10-2 mol) of methanesulfonic anhydride and 7.2 ml of toluene. 1.22 g of PCl5 was steeply added at room temperature. Exothermy, gas evolution and foaming was observed. The mixture was then heated up to 95 C. At about 40 C., formation of two well defined liquid phases were observed. The mixture was kept overnight at 95 C. No stirring problems arose. The mixture was then let to cool down to 80 C. at which point 7.2 ml of water were added dropwise (exothermy was observed). The mixture was stirred at 80 C. for 15 minutes and then let to cool down to room temperature. The aqueous layer was decanted and heated to 95 C. for 5.5 h and let to cool down to room temperature, at which point 7.2 ml of ethanol were added. The resulting mixture was cooled down to 5 C., stirred for 1 h and filtered. The solid washed with ethanol and dried at 40 C. in a vacuum oven until constant weight. 1.01 g of 3-pyridyl-1-hydroxyethylidene-1,1-bisphosphonic acid monohydrate are obtained (Yield: 58.23%) Chromatographic purity: 98.327% (area percent)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6419-36-9, 2-(Pyridin-3-yl)acetic acid hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; Serrano, Jordi Puig; Illado, Jordi Bosch; US2008/194525; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem