Category: pyridine-derivatives

Synthetic Route of 127406-55-7, 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. 127406-55-7, name is 4-Pyridin-3-yl-benzaldehyde, molecular formula is C12H9NO, 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.

[4-(6-Ethyl-thieno[2,3-d]pyrimidin-4-yl)-piperazin-1-yl]-(4-pyridin-3-yl-phenyl)-methanone The target acid was obtained (50 mg) by essentially following Step 1 of Example 437 using 4-pyridin-3-yl-benzaldehyde in place of 4-pyridin-4-yl-benzaldehyde. ES-MS: (M+H)+200

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 127406-55-7, 4-Pyridin-3-yl-benzaldehyde.

Reference:
Patent; Millennium Pharmaceuticals, Inc.; US2003/153556; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 86604-79-7, 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. 86604-79-7, name is 2,3,5-Trimethyl-4-nitropyridine 1-oxide. A new synthetic method of this compound is introduced below.

2,3,5-trimethyl-4-nitropyridine 1-oxide (850 g, 4.67 mol) was charged with water (400 g) and 36% concentrated hydrochloric acid (1.69 kg), and the resultant solution was heated to 70C. The solution was then charged with N,N-dimethylformamide (115 mL) and heated to 100C. Once the reaction had finished, the solution was cooled to 20C and then charged into a mixture of potassium carbonate (1.40 kg) and water (7 L). The resultant mixture was extracted with chloroform (1.0 L ¡Á 3), dried over sodium sulfate and then concentrated. The resultant crude product was stirred for 2 hours in a mixed solution of diisopropyl ether (500 mL) and n-hexane (1.0 L), and the resultant solution was then filtered with suction. The resultant wet substance was dried overnight under vacuum to obtain 666.4 g of the title compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,86604-79-7, 2,3,5-Trimethyl-4-nitropyridine 1-oxide, and friends who are interested can also refer to it.

Reference:
Patent; Eisai R&D Management Co., Ltd.; EP1875911; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1620-77-5, 5-Methylpicolinonitrile, 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, SDS of cas: 1620-77-5, blongs to pyridine-derivatives compound. SDS of cas: 1620-77-5

The compound of Example 4A (13 g, 110 mmol) is dissolved in 400 ml tetrachloro- methane, and 29.4 g (165 mmol) N-bromosuccinimide and 0.4 g (1.6 mmol) dibenzoylperoxide are added. The reaction reaction mixture is refluxed for three hours, cooled down to room temperature and filtered. The solution is washed with aqueous sodium thiosulfate, dried over magnesium sulfate, and the solvent is removed in [VACUO.] The residue is dissolved in 200 ml [DIOXANE AND] 200 ml water, calciumcarbonate (44 g, 440 mmol) is added, and the mixture is stirred at reflux for 2 hours. After cooling down to room temperature, the mixture is filtered, and dichloro- methane is added. After phase separation, the organic phase is dried over magnesium sulfate, and the solvent is removed in vacuo. The product is purified by chromato- graphy (silica, eluent [CYCLOHEXANE/ETHYL] acetate 2: 1). Yield : 5.2 g (35% [OF TH.)] [1H-NMR] (300 MHz, DMSO-d6): [8] = 4.7 (d, 2H), 5.6 (t, [1H),] 8.0 (m, 2H), 8.7 (s, 1H) ppm.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1620-77-5, 5-Methylpicolinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; BAYER HEALTHCARE AG; WO2004/24700; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 914942-88-4, 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 914942-88-4 as follows.

To a mixture of A214.5 (1.00 g, 5.74 mmol), tert~Butyl6-arnino-7-iodo-l- methyl-lH-imidazo[4,5-c]pyridin-4-yl(methyl)carbamate (1.78 g, 4.42 mmol), dichlorobis(triphenyl-phosphine)palladium II (0.186 g, 0.265 mmol), and copper EPO iodide (0.042 g, 0.221 mmol) in anhydrous dimethylformamide (12 mL) degassed well with nitrogen was added diisopropylamine (15 mL, 0.111 mol). The reaction mixture was immersed in an oil bath at 750C and stirred for 45 min. The solvent was removed under reduced pressure, and the residue was purified by flash silica gel chromatography using a mixture of methanol in dichloromethane (5%-8%) to give 1.88 g (95%) of A214.6 as a tan solid. The compound had an HPLC retention time = 2.13 min. (Column: Chromolith SpeedROD 4.6 x 50 mm – 4 min.; Solvent A = 10% MeOH, 90% H2O, and 0.1% TFA; Solvent B = 90% MeOH, 10% H2O5 and 0.1% TFA) and a LC/MS M+1 = 450.35.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,914942-88-4, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2006/122137; (2006); 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. 33674-96-3, name is (6-Bromopyridin-2-yl)methanol. A new synthetic method of this compound is introduced below., Recommanded Product: 33674-96-3

To a solution of (6-bromo-pyridin-2-yl)-methanol (2.00 g; 10.64 mmol) in 15 mL of dichloromethane is added dropwise phosphorus tribromide (0.61 mL; 6.44 mmol) at 0C. The mixture is warmed to room temperature and stirred overnight. Additional 100 muL of phosphorus tribromide is added and the reaction mixture is stirred for 3 hours at room temperature. The reaction is quenched with cooled NaHCO3 (half saturated aqueous solution) and extracted two times with dichloromethane. The combined organic layers are dried and concentrated under reduced pressure. (0563) Yield: 2.44 g (91 % of theory) (0564) Mass spectrometry (ESI+): m/z = 250/252 [M+H]+ (Br) (0565) HPLC (Method 1): Retention time = 0.878 min.

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, 33674-96-3, (6-Bromopyridin-2-yl)methanol.

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

Application of 351227-42-4, Adding some certain compound to certain chemical reactions, such as: 351227-42-4, name is 6-Chloro-4-iodopyridin-3-amine,molecular formula is C5H4ClIN2, 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 351227-42-4.

Route B : A mixture of 6-chloro-4-iodopyridin-3-ylamine (Preparation 8, 0.33g, 1.30mmol), pyruvic acid (0.27mL, 3.89mmol), DABCO (0.44g, 3.89mmol) and palladium acetate (0.015g, 0.07mmol) in dry DMF was stirred vigorously and degassed with argon for 15min. The reaction mixture was heated to 1070C for 5h. The reaction mixture was allowed to cool to rt and stirred for 16h. The volatiles were removed under reduced pressure and the residue partitioned between EtOAc (10OmL) and water (5OmL). The layers were separated and the aqueous extracted with EtOAc (2x50mL). The combined organics were extracted with aqueous NaOH (2M, 3x70mL). The combined aqueous extracts were acidified to pH 4 by careful addition of glacial acetic acid, then extracted with EtOAc (3x60mL). The combined organics were washed with brine (5OmL), dried (MgSO4), filtered and concentrated in vacuo to give the title compound as a brown solid. RT=2.72min, m/z (ES+) =197 [M+ H]+

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 351227-42-4, 6-Chloro-4-iodopyridin-3-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PROSIDION LIMITED; WO2006/59164; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 82454-61-3, 5-Ethynylpyridin-2-amine, 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, Application In Synthesis of 5-Ethynylpyridin-2-amine, blongs to pyridine-derivatives compound. Application In Synthesis of 5-Ethynylpyridin-2-amine

Copper(I) iodide (6.279 mg, 0.033 mmol) was added to a stirred mixture of intermediate 1-8 (913 mg, 3.297 mmol), 5-ethynyl-2-pyridinamine (779 mg, 6.594 mmol), Et3N (1.4 mL, 9.891 mmol), PdCl2(PPh3)2 (46 mg, 0.0659 mmol) and PPh3 (17.295 mg, 0.0659 mmol) in DMF (7.659 mL). The mixture was purged with nitrogen for 5 min and then it was stirred at 90 ¡ãC for 16h. The mixture was diluted with water and extracted with EtOAc. The organic layer was separated, dried (Na2S04), filtered and the solvents concentrated in vacuo. The crude product was purified by flash column chromatography (silica; MeOH in DCM 0/100 to 6/94). The desired fractions were collected and the solvents concentrated in vacuo. The residue was precipitated with DIPE and filtered to yield intermediate compound 1-24 (581 mg, 66percent) as a yellow solid

The synthetic route of 82454-61-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; ANDRES-GIL, Jose, Ignacio; VAN GOOL, Michiel, Luc, Maria; TRABANCO-SUAREZ, Andres, Avelino; DE LUCAS OLIVARES, Ana, Isabel; ALONSO-DE DIEGO, Sergio-Alvar; DELGADO-GONZALEZ, Oscar; (79 pag.)WO2016/16381; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 869557-43-7 ,Some common heterocyclic compound, 869557-43-7, molecular formula is C5H4BrFN2, 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 10 g of 2-amino-3-bromo-5-fluoropyridine, 19.2 g of 5-chloro-4-(trimethylstannyl)-2,3′-bipyridine A1, 4.24 g of tetrakis(triphenylphosphine)-palladium(0) and 2.095 g of copper (I) iodide in 120 ml of 1,4-dioxane is refluxed for 18 hours. The reaction medium is treated with aqueous 10% sodium hydrogen carbonate solution and then diluted with ethyl acetate. After separation of the phases by settling, the aqueous phase is extracted twice with ethyl acetate. The combined organic phases are dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue is taken up in a mixture of dichloromethane and methanol, and is then filtered by suction to give 11.67 g of 5′-chloro-5-fluoro-3,2′:4′,3-terpyridin-2-amine in the form of a beige-coloured solid. The filtrate is concentrated under reduced pressure and then taken up in dichloromethane, and silica is added. After concentrating under reduced pressure, the deposit is purified by chromatography on a column of silica, eluting with a 98/2 to 90/10 dichloromethane/methanol mixture to give 1.98 g of 5′-chloro-5-fluoro-3,2′:4′,3-terpyridin-2-amine in the form of a beige-coloured solid.UPLC-MS-DAD-ELSD: Tr (min)=2.71; [M+H]+: m/z 301; purity: 95%1H NMR (400 MHz, DMSO-d6): ppm: 5.78 (s, 2H) 7.47 (dd, J=8.8, 2.9 Hz, 1H) 7.55 (br. s., 1H) 8.06 (s, 1H) 8.12 (s, 1H) 8.49 (d, J=7.8 Hz, 1H) 8.68 (br, s., 1H) 8.84 (s, 1H) 9.35 (br. s., 1H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,869557-43-7, its application will become more common.

Reference:
Patent; SANOFI; US2012/208809; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 108-99-6, 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.108-99-6, name is 3-Methylpyridine, molecular formula is C6H7N, molecular weight is 93.13, as common compound, the synthetic route is as follows.

Example 7 The preparation of the catalyst of the present invention and the process for preparing nicotinic acid by using the catalyst 6.43 g of ammonium meta-vanadate were added into 500 ml water and the solution was heated at 70C to dissolve ammonium meta-vanadate. Then, 8.2 g of zinc sulfate were added into the solution and stirred for 30 minutes. Into the resultant solution were added 92.68 g titanium oxide (Hembitec K-03) and stirred for 1 hour. The mixture was heated to evaporate water and then calcined in an oven at a temperature of 600C to obtain the catalyst of the present invention, whose composition was shown in Table 1. After calcination, the catalyst was observed by electronic microscopy and found that the crystal size of the active ingredients on the surface of the carrier is from 40 to 60 nm. Subsequently, 30g of the prepared catalyst were fed into a tube reactor having a diameter of 1 inch and a length of 5 centimeter to obtain a catalyst bed. 3-Methylpyridine was first mixed with air and then with H2O vapor and then continuously fed into the catalyst bed at a mole ratio of 1:30:70 (3-methylpyridine: oxygen: H2O) and where the bed temperature was controlled at 320C . The feed speed of 3-methylpyridine is 0.025 hr-1. The product was collected at the outlet of the catalyst bed and analyzed by HPLC and GC. It was found that a conversion of 3-methylpyridine is 88.10%, a selectivity of nicotinic acid is 88.32%, and a selectivity of carbon dioxide is 9.25%.

The chemical industry reduces the impact on the environment during synthesis 108-99-6, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Chang Chun Petrochemical Co. Ltd.; EP1584618; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1124382-72-4, Adding some certain compound to certain chemical reactions, such as: 1124382-72-4, name is 2-Amino-8-bromo[1,2,4]triazolo[1,5-a]pyridine,molecular formula is C6H5BrN4, 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 1124382-72-4.

Intermediate 49 (16 g, 55.92 mmol) and water (75 mL) were added to a sol. of intermediate 51 (7.94 g, 37.28 mmol) in DME (200 mL). Then, Pd(PPh3)4 (4.31 g, 3.73 mmol) was added and the r.m. was stirred at 150 C for 10 min. under microwave irradiation. The mixture was filtered through diatomaceous earth and concentrated in vacuo. The crude product was purified by flash column chromatography (silica; eluent: DCM/(7 N NH3 in MeOH) from 100/0 to 97/3). The product fractions were collected and the solvent evaporated in vacuo to yield 7 g of a first fraction of intermediate 52. The impure fractions were also collected, evaporated in vacuo and the crude product was purified by RP preparative HPLC [RP Vydac Denali CI 8 (10 mm, 250 g, 5 cm); mobile phase: 0.25% NH4HC03 sol. in water/CH3CN]. The product fractions were collected and the solvent evaporated in vacuo. The crude product was further purified by RP preparative SFC [Diol; mobile phase: C02, MeOH (with 0.2% isopropylamine)]. The product fractions were collected and the solvent evaporated in vacuo to yield 4 g of a second fraction of intermediate 52. Yield: 11 g of intermediate 52 (quantitative yield).

According to the analysis of related databases, 1124382-72-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICALS, INC.; MINNE, Garrett, Berlond; BISCHOFF, Francois Paul; GIJSEN, Henricus, Jacobus, Maria; VELTER, Adriana, Ingrid; PIETERS, Serge, Maria, Aloysius; BERTHELOT, Didier, Jean-Claude; WO2013/10904; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem