Pyridine-derivatives

Reference of 1513-65-1, 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 1513-65-1 as follows.

Example 13: (4S)-Lambda/-Methyl-Lambda/-(f5-(4-methyl-1-piperazinvnimidazo? .2-aloyridin-2- v?methyl)-3,4-dihvdro-2H-pyranof3,2-b1pyridin-4-arnine EPO A) 6-Fluoro-2-pyridinamine: A solution of 2,6-difluoropyridine (50 g, 434 mmol) in ammonium hydroxide (200 mL, 28.0- 30.0%) was heated at 1050C in a steel bomb for 15 hours. The reaction was cooled in an ice bath and the precipitate filtered, rinsed with cold water, and dried to yield 6-fluoro-2- pyridinamine (45.8 g, 94% yield) as a white solid. 1H-NMR (CDCI3): delta 7.53 (m, 1 H)1 6.36 (dd, 1 H), 6.26 (dd, 1 H), 4.56 (s, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1513-65-1, its application will become more common.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/76131; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 78607-36-0, 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. 78607-36-0, name is 2-Chloro-3-iodopyridine. A new synthetic method of this compound is introduced below.

To a flame-dried flask were added Pd(PPh3)4 (10 mol %), Xantphos (10 mol %), Cs2CO3 (3 eq) and 2-chloro-3-iodopyridine (1.2 eq). Then, 1SI (1 eq) and DMF (0.15 M) were added to the reaction mixture under an N2 atmosphere. The reaction mixture was stirred for 10 min at room temperature, and then heated at 140 C. in a pre-heated oil bath for 24 h. After that, the reaction mixture was cooled to room temperature, diluted with CH2Cl2, filtered through a short pad of Celite, and washed with CH2Cl2. The combined organic extracts were concentrated under reduced pressure and the resulting residue was purified by column chromatography on silica gel to provide the product DFE-1S-2 in 67% yield.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,78607-36-0, 2-Chloro-3-iodopyridine, and friends who are interested can also refer to it.

Reference:
Patent; Arizona Board of Regents on behalf of Arizona State University; Li, Jian; Zhu, Zhi-Qiang; (232 pag.)US2018/337345; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 101083-92-5 ,Some common heterocyclic compound, 101083-92-5, molecular formula is C7H5N3O2, 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 43; [0221] This example illustrates a preparation of 6-methoxy-2-(l-methyl-lH-pyrrolo[2,3- delta]pyridin-5-yl)isoindolin-l-one in an embodiment of the invention.; Step A: Synthesis of l-methyl-5-nitro-7-azaindole,; [0222] A solution of 5-nitro-7-azaindole (0.195 g, 1.2 mmol) in DMF (10 mL) was treated with NaH (60%, 0.057 g, 1.44 mmol), followed by iodomethane (0.204 g, 1.44 mmol). The reaction mixture was stirred at room temperature for 4.5 h, then poured into water (200 mL) and extracted with dichloromethane (3 chi100 mL). The combined organic layer was washed with brine (100 mL), dried over sodium sulfate, and concentrated. The crude product was purified by chromatography (silica, 50:50 ethyl acetate/hexanes) to yield l-methyl-5-nitro-7-azaindole (0.152 g, 72%) as a yellow solid: 1H NMR (500 MHz, CDCl3) delta 9.23 (d, J= 2.4 Hz, IH), 8.76 (d, J= 2.4 Hz, IH), 7.36 (d, J= 3.6 Hz, IH), 6.66 (d, J= 3.5 Hz, IH), 3.96 (s, 3H).

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. 101083-92-5, 5-Nitro-1H-pyrrolo[2,3-b]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; The United States of America, as represented by the Secretary, Department of Health and Human Services; Science Applications International Corporation (SAIC); Albany Molecular Research, Inc.; WO2009/42907; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 76041-71-9, 3-Chloro-2-hydroxy-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, Recommanded Product: 76041-71-9, blongs to pyridine-derivatives compound. Recommanded Product: 76041-71-9

Preparation of N-({[3-chloro-5-(trifluoromethyl)pyridin-2-ylloxy}methyl)-2- (trifluoromethyl)benzamide (compound 1)To a solution of 0.20Og (1.01 mmol) of 3-chloro-5-(trifluoromethyl)pyridin- 2-ol in 5 ml of a mixture tetrahydofurane/NaOH IM (4/1) was added 0.263g {[2- (trifluoromethyl)benzoyl]amino}methyl acetate (1.01 mmol). The mixture was stirred 14 hours at room temperature.The reaction mixture was poured into 10ml of diethyl ether. Afire separation of the phases, the organic phase was washed twice with 5ml of water and dried over magnesium sulphate.After filtration, the solvent was evaporated and the residue was purified by flash chromatography on silica gel (eluent: heptane/ethyl acetate: 6/4) to give N-({[3- chloro-5-(trifluoromethyl)pyridin-2-yl]oxy}methyl)-2-(trifluoromethyl)benzamide: 298 mg (74%). Mass spectrum : 399 (M+ 1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,76041-71-9, 3-Chloro-2-hydroxy-5-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; BAYER CROPSCIENCE SA; WO2008/3744; (2008); A2;,
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. 800402-12-4, name is 2-Chloro-5-iodo-4-pyridinamine. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 2-Chloro-5-iodo-4-pyridinamine

2-(3-(4-Amino-6-chloropyridin-3-yl)prop-2-ynyl)-6-(thiophen-2- yl)pyridazin-3(2H)-one. A mixture o f Et3N (200 mul, 1435 mumol), Cu(I) (10 mg, 53 mumol), PdCl2(PhP3)2 (20 mg, 28 mumol), 2-(prop-2-ynyl)-6-(thiophen-2- yl)pyridazin-3(2H)-one (90 mg, 416 mumol), and 2-chloro-5-iodopyridin-4-amine (138 mg, 542 mumol) in MeCN (1.5 mL) was heated to 80 0C under nitrogen for 1 h. The mixture was cooled to room temperature, and was loaded to a silica column. Chromatography with 0.5-5% MeOH in CH2Cl2 afforded a pink solid which was triturated with EtOAc-hexane (1 :2, 10 mL) to give a pink solid as the pure product (48 mg). MS (ESI pos. ion) calc’d for Cj6Hi 1CIN4OS: 342.0; found 343.1 (MH+). 1H NMR (400 MHz, Chloroform-d) delta ppm 5.18 (s, 2 H) 5.75 (br. s., 2 H) 6.64 (s, 1 H) 7.03 (d, J=9.78 Hz, 1 H) 7.11 (dd, J=5.09, 3.72 Hz, 1 H) 7.37 – 7.48 (m, 2 H) 7.73 (d, J=9.78 Hz, 1 H) 8.03 (s, 1 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, 800402-12-4, 2-Chloro-5-iodo-4-pyridinamine.

Reference:
Patent; AMGEN INC.; WO2008/103277; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 7205-46-1 ,Some common heterocyclic compound, 7205-46-1, molecular formula is C7H6ClN3, 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.

4-Amino-3-ethyl-phenol (100 mg, 0.73 mmol, 1.0 equiv), 6-Chloro-l -methyl- 1H- imidazo[4,5-c]-pyridine (134 mg, 0.80 mmol, 1.1 equiv), Cs2C03 (714 mg, 2.19 mmol, 3.0 equiv), BetaGammaNuAlphaRho (46 mg, 0.07 mmol, 0.1 equiv), and Pd2(dba)3 (33 mg, 0.04 mmol, 0.05 equiv) were dissolved in dry dioxane (5 mL) under N2 atmosphere. The mixture was sonicated for 5 mn under N2 flow and then re fluxed for 20h. Full conversion was observed by LCMS. It was then cooled down and concentrated to dryness, diluted in DCM and washed with water (3x 20 mL). The aqueous layer was extracted with DCM (3x 30 mL) and the combined organic layer was dried over Na2SO i, filtered and concentrated to dryness. Purification was performed by column chromatography using the following eluant: EtOAc/Petroleum Ether (1 : 1) to EtOAc (over 5 CV), MeOH/EtOAc (1 : 19) (10 CV), MeOH/EtOAc (1 :9) (10 CV) to afford the desired compound

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,7205-46-1, its application will become more common.

Reference:
Patent; GALAPAGOS NV; MENET, Christel Jeanne Marie; SCHMITT, Benoit Antoine; GENEY, Raphael Jean Joel; DOYLE, Kevin James; PEACH, Joanne; PALMER, Nicholas John; JONES, Graham Peter; HARDY, David; DUFFY, James Edward Stewart; WO2013/117645; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 109-09-1, 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. 109-09-1, name is 2-Chloropyridine, molecular formula is C5H4ClN, 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.

Asolution of 2-chloropyridine ( XI) (9.39 mL, 0.1 mol) in, anhydrous THF (50 mL) was added slowly to a solution of LDA (2.0 M solution in THF/ hexane/ethylbenzene, 50 mL, 0.1 mol) in THF (200 mL) stirred at -78 C. under nitrogen. The stirring was continued at -78 C. for an additional 3 h before adding acetaldehyde (6.17 mL, 0.110 mol). The solution was stirred at -78 C. for another 2 h before allowing the temperature to rise to -40 C. A solution of water (4 mL) in THF (40 mL) was added slowly to the solution. When the temperature reached -10 C., additional water (200 mL) was added to the solution. The solution was extracted with ethyl ether (3×100 mL). The combined organic phase was dried over MgSO4, filtered and evaporated under reduced pressure to get a brown viscous residue. The crude product was purified on a flash silica gel column (1:1 DCM:hexane?100% DCM) to produce 1-(2-chloropyridin-3-yl)ethanol (XII) as a brown viscous oil (6 g, 38.1 mmol, 38% yield). 1H NMR (CDCl3) delta ppm 1.52 (d, J=6.41 Hz, 3H), 2.51 (brs, 1H), 5.24 (m, 1H), 7.28 (m, 1H), 7.97 (dd, J=7.72 Hz, J=1.70 Hz, 1H), 8.27 (dd, J=7.72 Hz, J=1.79 Hz, 1H).

According to the analysis of related databases, 109-09-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Samumed, LLC; Hood, John; Kumar KC, Sunil; Wallace, David Mark; US2013/296302; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 74115-12-1 , The common heterocyclic compound, 74115-12-1, name is 5-Chloro-3-hydroxypyridine, molecular formula is C5H4ClNO, 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 12 Preparation of Compound 7 (0241) (0242) To a 0 C. solution of 5-chloro-3-hydroxypyridine (3.00 g, 23.16 mmol) in tetrahydrofuran (90 mL) was added lithium tert-butoxide (1.0 M in THF, 23.16 ml, 23.16 mmol) dropwise, so as to maintain the internal reaction temperature below 10 C. (0243) In a separate flask, compound 12a (10.0 g, 22.1 mmol) was dissolved in tetrahydrofuran (50.0 mL). This solution was added dropwise to the lithium phenoxide solution over 2 min below 10 C. The cooling bath was then removed. This solution was then added dropwise to the lithium phenoxide solution over a 5 minute period while maintaining the internal reaction temperature below 10 C. The mixture was aged at 0-10 C. for 2 hours, then 0.5M aqueous citric acid (150 mL) and MTBE (100 mL) were added. The organics were dried over MgSO4, filtered, concentrated in vacuo, and purified using silica gel chromatography (0:100 to 70:30 EtOAc:Hexanes) to provide compound 7 (8.1 g, 22.4 mmol, 92% yield). 1H-NMR delta (ppm)(DMSO-d6): 1.11 (6H, dd, J=6.3, 3.3 Hz), 1.20 (3H, d, J=7.1 Hz), 3.89-3.97 (1H, m), 4.79-4.84 (1H, m), 6.71 (1H, dd, J=14.2, 10.1 Hz), 7.24 (1H, t, J=7.4 Hz), 7.29 (2H, d, J=8.1 Hz), 7.42 (2H, t, 7.8 Hz), 7.86 (1H, d, J=2.0 Hz), 8.47 (1H, s), 8.53 (1H, d, J=2.1 Hz).

The synthetic route of 74115-12-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EDWARDS, John Simon; MULLENS, Peter Richard; CLEATOR, Edward; MAGUIRE, Courtney K.; SCOTT, Jeremy Peter; ZHONG, Yong; FREY, Lisa F.; DORMER, Peter G.; KLAPARS, Artis; ASHLEY, Eric; QIAN, Pu; MERCK SHARP & DOHME CORP.; MERCK SHARP & DOHME LIMITED; Edwards, John; Mullens, Peter Richard; Cleator, Ed; Simmons, Bryon L.; Maguire, Courtney K.; Scott, Jeremy Peter; Yasuda, Nobuyoshi; Zhong, Yong-Li; Frey, Lisa F.; Dormer, Peter G.; Brunskill, Andrew; Klapars, Artis; Qian, Puneet; Zhang, Yi; Wan, Baoqiang; (23 pag.)US2017/275327; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 108130-10-5, name is Ethyl 2,6-dichloro-4-methylnicotinate, the common compound, a new synthetic route is introduced below. Product Details of 108130-10-5

a) Synthesis of 6-chloro-2-(ethyl(methyl)amino)-4-methyl-pyridine-3-carboxylic acid ethylester A mixture of 8.2 g (35.0 mmol) 2,6-dichloro-4-methyl-pyridine-3-carboxylic acid ethylester, 3.7 ml (43.8 mmol) N-methylethylamine and 8.9 ml (52.5 mmol) DIPEA in NMP (25 ml) was heated in the MW to 90 C. for 1 h. Then the solution was diluted with water, a 1M aq. NaOH sol. and EtOAc. The organic layer was separated, dried over MgSO4 and concentrated in vacuo. Purification of the residue by CC (hexane/EtOAc 9:1) provided 4.0 g (15.6 mmol, 44%) 6-chloro-2-(ethyl(methyl)amino)-4-methyl-pyridine-3-carboxylic acid ethylester.

The synthetic route of 108130-10-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Grunenthal GmbH; US2012/101079; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 14237-71-9, 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 14237-71-9, name is 2-Chloro-4,6-dimethylnicotinonitrile. This compound has unique chemical properties. The synthetic route is as follows.

2-chloro-4,6-dimethyl-nicotinonitrile (2.5 g, 15.01 mmol) was dissolved in anhydrous methanol (70mL), added with sodium methoxide (4. 27 g, 75.03 mmol) at 0 C and stirred for about 10 hours at nitrogen atmosphere. The above mixture was concentrated under reduced pressure and then neutrailized with a saturated solution of ammonium chloride and then extracted twice with 150 mL of methylenechloride. The resulting organic layer was dried using anhydrous sodium sulfate, filtered and concentrated. A silica gel column chromatography (20% EtOAc/Hexanes) was performed on the resulting residue and 2.41g (99%) of 2- methoxy-4, 6-dimethyl-nicotinonitrile was obtained in white solid. ‘H NMR (300 MHz, CDC13) 8 2.44 (s, 3H), 2.45 (s, 3H), 4.01 (s, 3H), 6.68 (s, 1H).

According to the analysis of related databases, 14237-71-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SK CHEMICALS, CO., LTD.; WO2005/63768; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem