Category: pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 17322-91-7, 1H-Pyrrolo[3,2-b]pyridin-5(4H)-one, 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 1H-Pyrrolo[3,2-b]pyridin-5(4H)-one, blongs to pyridine-derivatives compound. Quality Control of 1H-Pyrrolo[3,2-b]pyridin-5(4H)-one

Dissolve 5-hydroxy-1H-pyrrole [3,2] pyridine (10 mmol) in 40 ml of dichloromethane solution.10 ml of triethylamine was added thereto, and the temperature was controlled below 10 C.A solution of 2-chloroacetyl chloride (12 mmol) in dichloromethane was added dropwise to the system.After the addition was completed, the temperature was returned to room temperature, and the mixture was stirred at room temperature for 10 hours.The reaction system was then washed with 50 ml of a 5% aqueous solution of sodium carbonate and the organic phase was dried over anhydrous Na2SO4.After evaporating the solvent, the obtained solid was separated by flash column chromatography.1.9 g of pale yellow 2-chloro-1-(5-hydroxy-1H-pyrrole[3,2]pyridin-1-yl)-ethanone solid were obtained in a yield of 90%.

The synthetic route of 17322-91-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sang Qi; (10 pag.)CN108456207; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 51173-05-8, 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 51173-05-8, name is 5-Fluoro-2-hydroxypyridine. This compound has unique chemical properties. The synthetic route is as follows.

a) 5-Fluoro-3-nitropyridin-2-ol A mixture of concentrated sulphuric acid (1 mL) and fuming nitric acid (1 mL) was added dropwise to a stirred, cooled (ice-bath) mixture of 5-fluoropyridin-2-ol (1.20 g, 10.6 mmol) and concentrated sulphuric acid (2.7 mL). The mixture was warmed to ambient temperature and then to 85 C. After 2 hours, the mixture was cooled and poured onto ice-water. The precipitate was filtered and dried to give the title compound (0.72 g, 43%) as a yellow solid. LRMS (m/z): 157 (M-1)+. 1H NMR delta (300 MHz, DMSO-d6): 8.28 (s, 1H), 8.67 (s, 1H).

According to the analysis of related databases, 51173-05-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Almirall, S.A.; EP2527344; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 877060-48-5 , The common heterocyclic compound, 877060-48-5, name is tert-Butyl 3-iodo-1H-pyrrolo[3,2-c]pyridine-1-carboxylate, molecular formula is C12H13IN2O2, 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.

1.1 140 mg (0.20 mmol) of bis(triphenylphosphine)palladium(II)chloride and 15 mg (0.08 mmol) of copper(I)iodide are added to a solution, kept under nitrogen, of 1.37 g (4.00 mmol) of tert-butyl 3-iodopyrrolo[3,2-c]pyridine-1-carboxylate (prepared by the method of M. Lefoix et al, Synthesis, 2005, 20, 3581-3588) in 20 ml of tetrahydrofuran. Carbon monoxide is passed into this solution in an autoclave apparatus, and the mixture is stirred at a pressure of about 5 bar for 50 minutes. The apparatus is decompressed, 589 mg (6.00 mmol) of trimethylsilylacetylene and 405 mg (4.00 mmol) of triethylamine are added under nitrogen. The apparatus is re-pressurised to 5.8 bar with carbon monoxide, and the reaction mixture is stirred at room temperature for 45 hours. Saturated sodium chloride solution is added to the reaction mixture, which is then extracted with dichloromethane. The organic phase is dried over sodium sulfate and evaporated. The residue is chromatographed on a silica-gel column with petroleum ether/ethyl acetate as eluent: tert-butyl 3-(3-trimethylsilylpropynoyl)pyrrolo-[3,2-c]pyridine-1-carboxylate as yellowish crystals; ESI 343.1.2 104 mg (0.75 mmol) of potassium carbonate are added to a solution of 103 mg (0.30 mmol of tert-butyl 3-(3-trimethylsilylpropynoyl)pyrrolo-[3,2-c]pyridine-1-carboxylate and 148 mg (0.75 mmol) of phenylguanidine carbonate in 1.5 ml of ethylene glycol monomethyl ether, and the mixture is heated at the boil for 68 hours. After cooling, 10 ml of water are added, and the mixture is stirred at 40 C. for 1 h. The precipitate formed is filtered off with suction, washed with water and dried in vacuo, giving phenyl-[4-(1H-pyrrolo[3,2-c]pyridin-3-yl)pyrimidin-2-yl]amine (?A1?) as pale-brown solid; ESI 287;1H NMR (DMSO-d6) delta [ppm] 6.90 (t, J=7.5 Hz, 1H), 7.25 (m, 3H), 7.39 (d, J=5.5 Hz, 1H), 7.76 (d, J=7.5 Hz, 2H), 8.22 (d, J=5.5 Hz, 1H), 8.32 (d, J=5.5 Hz, 1H), 8.35 (s, 1H), 9.46 (s, 1H), 9.81 (s, 1H), 12.0 (bs, 1H).

The synthetic route of 877060-48-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK PATENT GESELLSCHAFT; US2011/92527; (2011); 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.153747-97-8, name is tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate, molecular formula is C14H20BrN3O2, molecular weight is 342.23, as common compound, the synthetic route is as follows.Quality Control of tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate

[0957] Into a 2 L 4-necked round-bottom flask, purged andmaintained with an inert atmosphere ofnitrogen, was placeda solution of compound 90e (42.8 g, 206 mmol) in 1,4-dioxane (1 L), compound 90b (80.0 g, 206 mmol), Pd(dppf)Cl2 (7.53 g, 10.3 mmol) andCs 2C0 3 (167 g, 514 mmol). Thereaction mixture was stirred overnight at 90 C. Upon cooling, the reaction was quenched with water (100 mL). Theresulting mixture was extracted with DCM. The combinedorganic layers were dried over Na2S04 , filtered and concentrated underreduced pressure. The resultant residue was purified by flash column chromatography on silica gel (DCM/MeOH (1 00:3 v/v)) to obtain compound 90fas a yellow solid(23.0 g, 29% yield). Mass Spectrum (LCMS, ESI pos.):Calcd. for C18H23ClN60 2 : 391.2 (M+H). found 391.1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,153747-97-8, tert-Butyl 4-(5-bromopyridin-2-yl)piperazine-1-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; JANSSEN PHARMACEUTICA, NV; Player, Mark R.; Meegalla, Sanath K.; Illig, Carl R.; Chen, Jinsheng; Wilson, Kenneth J.; Lee, Yu-Kai; Parks, Daniel J.; Huang, Hui; Patel, Sharmila; Lu, Tianbao; US2014/364414; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 824-52-2, Adding some certain compound to certain chemical reactions, such as: 824-52-2, name is 5-Methyl-1H-pyrrolo[2,3-b]pyridine,molecular formula is C8H8N2, 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 824-52-2.

To 5-methyl-lH-pyrrolo[2,3-b]py?dine (IS, 2 00 g, 15 1 mmol) and aluminum trichloride (1 1 6 g, 87 2 mmol), nitromethane (63 1 mL, 1 16 mol) was added, followed by the addition of 2,6- difluoro-3-nitro-benzoyl chlonde (14, 3 22 g, 14 5 mmol) The reaction was placed in an oil bath at 45 0C and stirred for 3 days, then cooled to room temperature and 30 mL of methanol was added The reaction was then diluted with 200 mL of ethyl acetate and 100 mL each of water and IN hydrochloric acid, resulting in a precipitate that was collected to provide the desired compound (16, 2 761 g) Additonal compound was recovered from the organic layer, removing the solvent and purifying by silica gel column chromatography eluting with a gradient of 5 to 70% ethyl acetate in hexanes to provide another 126 mg of compound MS(ESI) [M+H+]+ = 317 9

According to the analysis of related databases, 824-52-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PLEXXIKON, INC.; IBRAHIM, Prabha, N.; SPEVAK, Wayne; CHO, Hanna; SHI, Songyuan; WU, Guoxian; WO2010/129567; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 117873-72-0, 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 117873-72-0, name is 2,6-Dibromo-4-methoxypyridine. This compound has unique chemical properties. The synthetic route is as follows.

(1) Production of 2-bromo-4-methoxy-6-{3-(trifluoromethyl)phenoxy} pyridine as an intermediate product 3.34 g (0.187*1.1 mol) of 3-(trifluoromethyl) phenol was dissolved in about 30 ml of dimethyl formamide. The solution was further mixed with 0.78 g (ca. 60% in mineral oil; 0.0187*1.04 mol) of sodium hydride and then with 5.00 g (0.0187 mol) of 2,6-dibromo-4-methoxy pyridine. After stirring at about 120 C. for about 2 hours, the mixture was allowed to stand for cooling to room temperature. After the reaction solution was distributed with hexane-saturated sodium bicarbonate water, the organic phase of the obtained solution was washed with saturated brine and dried with anhydrous sodium sulfate. The resultant solution was concentrated and then purified by silica gel column chromatography (eluding solution: ethyl acetate/hexane), and the obtained product was subjected to recrystallization using hexane, thereby obtaining an aimed product. Yield by weight: 3.23 g; yield by percentage: 50%; solid; melting point: 57 to 60 C.; 1 H-NMR (60 MHz, CDCl3, delta): 3.75 (3H, s), 6.26 (1H, d, J=2 Hz), 6.75 (1H, d, J=2 Hz), 7.0-7.6 (4H, complex).

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 117873-72-0, 2,6-Dibromo-4-methoxypyridine.

Reference:
Patent; Kureha Kagaku Kogyo Kabushiki Kaisha; US6005112; (1999); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 52605-96-6, 2-Chloro-3-methoxypyridine, 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, Computed Properties of C6H6ClNO, blongs to pyridine-derivatives compound. Computed Properties of C6H6ClNO

The 2-chloro-3-methoxypyridine (2) (13 g, 90.6 mmol), from Step I, was stirred with 3- equivalents of sodium methoxide (14.7 g, 271.8 mmol) in dimethylformamide (100 mL) at 10O0C until completion of the reaction. The reaction mixture was then quenched with water and extracted with dichloromethane. The combined extracts were washed with water, concentrated and distilled (74C; 5 mm Hg) to give the product, 2,3-dimethoxypyridine (3), as a clear oil (7 g; 29 % yield for two steps).1H NMR (300 MHz, CDCl3) delta 7.65 (dd, 1 H, Ji = 5.1 Hz, J2 = 1.5 Hz), 6.96(dd, 1 H, Ji = 7.5 Hz, J2 = 1.5 Hz), 6.76(dd, 1 H, J, = 5.1 Hz, J2 = 7.7 Hz), 3.95 (s, 3 H), 3.80 (s, 3 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,52605-96-6, 2-Chloro-3-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; BIONUMERIK PHARMACEUTICALS, INC.; WO2007/123995; (2007); A2;,
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. 6945-67-1, name is 2-Bromo-4-nitropyridine. A new synthetic method of this compound is introduced below., Quality Control of 2-Bromo-4-nitropyridine

EXAMPLE 47 To a suspension of 2-bromo-4-nitropyridine (406 mg), 3-aminophenylboronic acid (403 mg) and tetrakis(triphenylphosphine)-palladium (116 mg) in 1,2-dimethoxyethane (10 ml) was added 2M aqueous solution of sodium carbonate (2.6 ml). The mixture was stirred at 80 C. for 7 hours under a nitrogen atmosphere, then cooled to room temperature and diluted with ethyl acetate. The organic layer was separated, washed with water and brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure to give crude 3-(4-nitropyridin-2-yl)aniline. This compound was used for next step without purification.

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, 6945-67-1, 2-Bromo-4-nitropyridine.

Reference:
Patent; Fujisawa Pharmaceutical Co., Ltd.; US6521643; (2003); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 19346-43-1, 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. 19346-43-1, name is 2-Fluoro-3-nitro-4-picoline, molecular formula is C6H5FN2O2, 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.

18. Preparation of 3-Amino-2-fluoro-4-methylpyridine To a solution of 10.1 g (65 mmol) of 2-fluoro-4-methyl-3-nitropyridine in 200 mL of ethyl acetate was added 25 g (0.40 mol) of acetic acid and 0.8 g of 5 percent palladium on carbon catalyst. This mixture was shaken under 50 psig (pounds per square inch gauge) (2400 kiloPascals) pressure of hydrogen for 18 hours, was filtered, and was concentrated by evaporation under reduced pressure to obtain an oil. This oil was partitioned between dilute aqueous sodium bicarbonate and ether. The organic phase was separated, dried over magnesium sulfate, and filtered. The filtrate was concentrated by evaporation under reduced pressure and the residue was purified by column chromatography to obtain 7.2 g (88 percent of theory) of the title compound as a colorless solid, melting at 63-64 C. Nuclear Magnetic Resonance Spectrum (200 MHz (megaHertz), CDC13): 1 H: 7.4 (d, 1H, J=5.0); 6.8 (d, 1H, J=5.0); 3.7 (br, 2H); 2.1 (s, 3H); 13 C: 152.6 (d, J=229); 134.1 (d, J=8.6); 133.8 (d, J=14.5); 128.1 (d, J=27.1); 123.3, 16.4 (d, J=4.1).

According to the analysis of related databases, 19346-43-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DowElanco; US5602075; (1997); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 914358-72-8 ,Some common heterocyclic compound, 914358-72-8, molecular formula is C6H5BrClN, 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.

Example 60(1r,4r)-6′-(5-Chloro-6-methylpyridin-3-yl)-4-methoxy-5”-methyl-3’H-dispiro[cyclohexane-1,2′-indene-1′,2”-imidazol]-4”-amine; 4,4,4′,4′,5,5,5′,5′-Octamethyl-2,2′-bi(1,3,2-dioxaborolane) (287 mg, 1.13 mmol), (1r,4r)-6′-bromo-4-methoxy-5”-methyl-3’H-dispiro[cyclohexane-1,2′-indene-1′,2”-imidazol]-4”-amine (Example 19, 213 mg, 0.57 mmol) and potassium acetate (167 mg, 1.70 mmol) and dioxane (3 mL) were added and the mixture was degassed with a stream of argon (g) for a couple of min. PdCl2(dppf) CH2Cl2 (32.4 mg, 0.04 mmol) was added and the mixture was heated to reflux for 1.5 h under N2 atmosphere. 4,4,4′,4′,5,5,5′,5′-Octamethyl-2,2′-bi(1,3,2-dioxaborolane) (120 mg, 0.47 mmol) was added and the reaction was heated to reflux overnight. The volatiles were removed in vacuo and 80 mg of the residue ((1r,4r)-4-methoxy-5”-methyl-6′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3’H-dispiro[cyclohexane-1,2′-indene-1′,2”-imidazol]-4”-amine (MS (ES+) m/z 424 [M+H]+) was mixed with 5-bromo-3-chloro-2-methylpyridine (Intermediate 43, 47 mg, 0.23 mmol), K2CO3 (0.38 mL, 0.76 mmol) and dioxane (2 mL). The mixture was degassed with a stream of argon (g) for a couple of min. PdCl2(dppf) CH2Cl2 adduct (138 mg, 0.19 mmol) was added. The vial was sealed and heated in a microwave reactor at 140 C. for 30 min. EtOAc was added and the mixture was washed with brine and water. The organic phase was dried with MgSO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography (12 g SiO2, 0-20% MeOH containing 0.1 M NH3 in DCM). The crude product was purified with preparative chromatography. The fractions containing product were combined and concentrated. The water phase was extracted with DCM and the phases were separated using a phase separator. The organic phase was concentrated in vacuo yielding the title compound (5 mg, 6% yield): 1H NMR (CD3OD) delta ppm 1.11 (td, 1H), 1.24-1.43 (m, 2H), 1.49 (td, 1H), 1.63 (td, 2H), 1.90-2.00 (m, 2H), 2.32 (s, 3H), 2.61 (s, 3H), 3.04-3.12 (m, 1H), 3.15 (d, 1H), 3.25 (d, 1H), 3.33 (s, 3H), 6.99 (d, 1H), 7.47 (d, 1H), 7.55 (dd, 1H), 7.99 (d, 1 H), 8.51 (d, 1H); MS (MM-ES+APCI)+ m/z 423 [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,914358-72-8, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; US2012/165347; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem