Category: pyridine-derivatives

Application of 73870-24-3 ,Some common heterocyclic compound, 73870-24-3, molecular formula is C6H7Br2N, 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.

Step 3 To a suspension of NaH (170 mg of a 60% dispersion in mineral oil, 4.25 mmol) in anhydrous DMF (20 ml) is added 2,2,2-trifluoro-N-{4-[(2,2,2-trifluoro-acetylamino)-methyl]-piperidin-4-yl}-acetamide hydrochloride) (500 mg, 1.4 mmol) followed by 4-bromomethylpyridine hydrobromide (350 mg, 1.4 mmol). The reaction mixture is stirred at room temperature for 3 hours. The reaction mixture is quenched with sat. NH4Cl solution and is concentrated in vacuo. The residue is purified by column chromatography (basic alumina, MeOH/DCM) to obtain 2,2,2-Trifluoro-N-[1-pyridin-4-ylmethyl-4-(2,2,2-trifluoro-acetylamino)-piperidin-4-ylmethyl]-acetamide as off-white solid; [M+H]+ 413.

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. 73870-24-3, 4-(Bromomethyl)pyridine hydrobromide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Vertex Pharmaceuticals Incorported; US2011/98311; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1232431-75-2, 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 1232431-75-2, name is 4-Bromopyridine-2,3-diamine. This compound has unique chemical properties. The synthetic route is as follows.

2,3-diamino-4-bromopyridine (320 mg, 1.7 mmol)Mix with 20 ml of dimethyl oxalate, warm to reflux and stir for 3-4 hours.After the reaction solution was cooled, the resulting solid was filtered off.The solid was dispersed in 15 ml of N,N-dimethylformamide.Add 1 g of activated carbon, raise the temperature to reflux, and filter it hot after 1 hour.1 ml of water was added to the filtrate and allowed to stand for 1 hour.The precipitated white solid is filtered and washed with water.95% ethanol wash,Ethyl acetate wash to give 8-bromo-5-azaquinoxaline-2,3-dione white solid(332 mg, yield 80.6%).

According to the analysis of related databases, 1232431-75-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai Jiao Tong University; Wang Yongxiang; Fu Lei; Xie Dongsheng; Lu Jun; (37 pag.)CN103435561; (2016); B;,
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. 79055-62-2, name is 2-Chloro-5-methylpyridin-4-amine. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 79055-62-2

Step A: Preparation of 2′-chloro-4-hydroxy-6,5′-dimethyl-[1,4′]bipyridinyl-2-one To a screw top vial with rubber septa inset was added 2,2-dimethyl-6-(2-oxo-propyl)-[1,3]dioxin-4-one, prepared as described in Organic Letters, 11(21), 4910-4913; 2009, (500 mg, 2.7 mmol) and 2-chloro-5-methyl-pyridin-4-ylamine (575 mg, 4 mmol, 1.5 eq). The mixture was dissolved in anhydrous 1,4-dioxane (10 mL). Once the mixture was homogeneous the vial was placed on a stirrer/hot plate preset to 90° C. The reaction vessel was heated at this temperature for 3.5 h. The reaction vial was removed from heat and analyzed by HPLC which showed that the reaction was >95percent complete. The vial was placed back on the hot plate. To the heated mixture was added H2SO4 (250 muL) and the reaction was heated for 1 h. The reaction vial was removed from the heat and after cooling to ambient temperature, the dioxane was removed by passing a stream of air over the top of the open vial to give a brown residue. Water (?4 mL) was added to the vial, and the mixture was stirred for 30 min. The resulting tan solid was filtered off with washing from additional water and the diethyl ether to give the desired product (531 mg, 57percent based on being the sulfate salt) as a tan solid which by HPLC was ?95percent pure: MS (ES) m/e 250 (M+H).

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, 79055-62-2, 2-Chloro-5-methylpyridin-4-amine.

Reference:
Patent; Hockerman, Susan L.; Monahan, Joseph B.; Selness, Shaun R.; US2014/364442; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 102368-13-8, 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.102368-13-8, name is 1,1′-Thiocarbonylbis(pyridin-2(1H)-one), molecular formula is C11H8N2O2S, molecular weight is 232.2584, as common compound, the synthetic route is as follows.

b) (2,4-Dichloro-3-isothiocyanato-benzyl)-carbamic acid tert-butyl ester 1,1′-Thiocarbonyldi-2-pyridone (0.42 g, 1.8 mmol) was added to a mixture of (3-amino-2,4-dichloro-benzyl)-carbamic acid tert-butyl ester (0.50 g, 1.7 mmol) and dioxane (25 mL) and stirred at rt for 2 h and at reflux for 2 d. The mixture was concentrated, diluted with DCM and filtered over silica gel. The filtrate was concentrated to give the sub-title compound. Yield: 0.49 g (86%). Rf=0.83 (silica gel, DCM:EtOH 95:5).

The chemical industry reduces the impact on the environment during synthesis 102368-13-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2012/309738; (2012); A1;,
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. 88912-27-0, name is 3-Chloroisonicotinic acid, molecular formula is C6H4ClNO2, 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. HPLC of Formula: C6H4ClNO2

Reference Production Example 26To a mixture of 0.58 g of WSC and 5 ml of pyridine 5ml, 0.48 g of 3- chloroisonicotinic acid was added. The reaction mixture was stirred at room temperature for 25 minutes. To the reaction mixture, 0.75 g of 2-amino-4-(heptafluoroisopropyl)phenol was added and was stirred while heating at 60C for three hours. The reaction mixture was cooled to room temperature, the 0.24 g of 3-chloroisonicotinic acid and 0.29 g of WSC was added and stirred while heating at 60C for 1.5 hours and then at 80C for 1.3 hours. The mixture reaction was cooled to room temperature, and then concentrated under reduced pressure. Then, water was added to the residue, followed by extraction with ethyl acetate twice. The combined organic layers were washed with a saturated sodium chloride solution, was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.90 g of 3-chloro-N-[2- hydroxy-5-(heptafluoroisopropyl)phenyl]isonicotinamide.1H-NMR (DMSO-d6) delta: 10.19 (br s, 1H), 8.75 (s, 1H), 8.63 (d, J=4.9 Hz, 1H), 8.36 (d, J=1.9 Hz, 1H), 7.65 (d, J=4.9 Hz, 1H), 7.32 (dd, J=8.8, 2.0 Hz, 1H), 7.12 (d, J=8.8 Hz, 1H)

With the rapid development of chemical substances, we look forward to future research findings about 88912-27-0.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; OTSUKI, Junko; WO2011/49223; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 778611-64-6, 5-Bromo-2-chloro-4-methylpyridine, 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, 778611-64-6, blongs to pyridine-derivatives compound. Safety of 5-Bromo-2-chloro-4-methylpyridine

Step 1: A mixture of compound 9-1 and aqueous EtNH2 (10 mL) in NMP (5 mL) was stirred for 3 days at 80C in a sealed tube, then concentrated. The residue was diluted with EtOAc (50 mL), washed with H20 (10 mL), brine (10 mL), dried over anhydrous Na2S04, concentrated, and purified by column chromatography, eluting with PE/EA = 4/1 to give target compound 9-2 as yellow oil. LC-MS: m/z = 215.0 [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,778611-64-6, its application will become more common.

Reference:
Patent; BIOGEN IDEC MA INC.; HUTCHINGS, Richard, H.; JONES, John, Howard; CHAO, Jianhua; ENYEDY, Istvan, J.; MARCOTTE, Douglas; WO2014/28669; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 14432-12-3, 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. 14432-12-3, name is 4-Amino-2-chloropyridine. A new synthetic method of this compound is introduced below.

NaHMDS (9 mL, 2 M, 18 mmol) was added dropwise to a solution of 2-chloro-4-aminopyridine (1.0 g, 7.8 mmol) in dry tetrahydrofuran (30 mL) at 0C under N2. After continuously stirred for 30 min, a solution of ditertbutyl dicarbonate (3.75 g, 17 mmol) in dry tetrahydrofuran was added. The reaction mixture was stirred overnight at room temperature, and then poured into saturated ammonium chloride solution. The mixture was extracted with ethyl acetate, and the organic layer was washed by saturated brine, concentrated under vacuum to remove the solvent.The resulting residue was purified by column chromatography (petroleum ether :ethyl acetate = 8:1) to afford the title compound (923 mg, 36 %). 1H NMR (CDCl3): delta 8.39 (1H, d, J = 5.2 Hz), 7.19 (1H, d, J = 1.6 Hz), 7.05 (1H, dd, J = 1.6 Hz, 5.2 Hz), 1.47 (18H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,14432-12-3, its application will become more common.

Reference:
Patent; Li, Yuliang; WANG, Huting; ZHU, Yan; WANG, Zhe; ZHANG, Hui; ZHAO, Ruiyu; HUANG, Yuanyuan; WANG, He; PENG, Yong; LUO, Hong; XIAO, Dengming; CAO, Shousong; HAN, Yongxin; EP2862571; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 192189-16-5, Adding some certain compound to certain chemical reactions, such as: 192189-16-5, name is tert-Butyl 3-bromo-1H-pyrrolo[3,2-c]pyridine-1-carboxylate,molecular formula is C12H13BrN2O2, 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 192189-16-5.

Intermediate 2 (33.0 mg, 0.10 mmol) was mixed with 80% aqueous dimethoxyethane (1 mL), 4-chlorophenylboronic acid (23.0 mg, 0.15 mmol) and K2CO3 (35.0 mg, 0.25 mmol). Tetrakis-(triphenylphosphine)palladium(0) (6.00 mg, 0.005 mmol) was added and the mixture was stirred at 80 C for 80 min. After cooling, water (0.8 mL) and EtOAc (8 mL) were added. The mixture was centrifuged and the organic layer was separated. Flash chromatography (1 :3 EtO Ac/toluene) gave the title compound (21 mg, 64%). HRMS (ESI+) calcd for Ci8H17ClN202 328.0979, found 328.0980.

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. 192189-16-5, tert-Butyl 3-bromo-1H-pyrrolo[3,2-c]pyridine-1-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Proximagen Limited; EVANS, David; CARLEY, Allison; STEWART, Alison; HIGGINBOTTOM, Michael; SAVORY, Edward; SIMPSON, Iain; NILSSON, Marianne; HARALDSSON, Martin; NORDLING, Erik; KOOLMEISTER, Tobias; WO2011/113798; (2011); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6295-87-0, 1-Aminopyridinium Iodide, 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, COA of Formula: C5H7IN2, blongs to pyridine-derivatives compound. COA of Formula: C5H7IN2

General procedure: A clean, washed boiling tube equipped with a magnetic stir bar was charged with 1-aminopyridinium iodide (1a) (0.0665 g, 0.3 mmol),(E)-chalcone (2a) (0.0520 g, 0.25 mmol) and NMP (1 mL). The mixture was stirred for 24 h at r.t. under O2 (balloon). After completion of the reaction, the mixture was poured into hypo solution (10 mL). The mixture was extracted with EtOAc (3 × 10 mL), dried over anhydrous Na2SO4 and the solvent removed under reduced pressure. The residue was purified through column chromatography using silica gel (20%EtOAc/hexane) to afford 3a.

The synthetic route of 6295-87-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ravi, Chitrakar; Samanta, Supravat; Mohan, Darapaneni Chandra; Reddy, N. Naresh Kumar; Adimurthy, Subbarayappa; Synthesis; vol. 49; 11; (2017); p. 2513 – 2522;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 113975-22-7, 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. 113975-22-7, name is 2-Fluoro-3-iodopyridine, molecular formula is C5H3FIN, 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.

NaO’Bu, 150C [00209] A microwave reaction vessel was charged with 2-fluoro-3-iodopyridine(purchased from Maybridge) (0.565 g, 2.53 mmol), morpholine (purchased from Aldrich) (0.221 ml, 2.53 mmol), Pd2(dba)3(purchased from Strem) (0.154 g, 0.152 mmol), 2- dicyclohexylphosphino-2′,6′-dimethoxy-l, -biphenyl (purchased from Strem) (0.135 g, 0.304 mmol), and sodium t-butoxide (0.8 g, 7.6 mmol). The reaction mixture was stirred and heated in a Discover model microwave reactor (CEM, Matthews, NC) at 150C for 20 min (125 watts, Powermax feature on, ramp time 5 min). Solvent was evaporated. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Biotage pre-packed silica gel column, eluting with a gradient of 1% to 5% MeOH in CH2CI2, to provide 4-(2-fhioropyridin-3- yl)morpholine (0.311 g, 67.5% yield).

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 113975-22-7, 2-Fluoro-3-iodopyridine.

Reference:
Patent; AMGEN INC.; ALLEN, Jennifer; HORNE, Daniel B.; HU, Essa; KALLER, Matthew R.; MONENSCHEIN, Holger; NGUYEN, Thomas T.; REICHELT, Andreas; RZASA, Robert M.; WO2011/143495; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem