Pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 722550-01-8, 4-(Pyrrolidin-1-yl)pyridin-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, 722550-01-8, blongs to pyridine-derivatives compound. SDS of cas: 722550-01-8

General procedure: 2,4-Dimethoxy-5-[7-(pyrrolidin-1-yl)imidazo|1,2-a]pyridin-2-yl]benzonitrile 63a was prepared in the same manner as 2-(5-bromo-2,4-dimethoxyphenyl)-7-(pyrrolidin-1-yl)imidazo[1,2-a]pyridine 9a and was obtained as an off-white solid (62% yield). The resulting compound was treated with HBr to obtain the desired hydrobroniide salt. 1H NMR (400 MHz, DMSO-d6): delta 8.49 (d. J= 7,4 Hz, 1H), 8.23 (s, IH), 8, 14 (s, IH), 7.00 (s, IH), 6.97-6.91 (m, III), 6,31 (s, I H), 4.12 (s, 3H), 4.04 (s, 3H), 3.44 (s, 4H), 2.03 (s, 4H). HPLC (Method 2) 97.12% (AUC), = 18.09 rnm. ESI MS m/z 349 [M + H | +. A solution of 2-bromo-1-(5-bromo-2,4-dimethoxyphenyl)ethanone 7 (124 rng, 0.367 mmol) and 4-(pyrrolidin-1-yl)pyridin-2-amine 8 (60 mg, 0.367 mmol) in acetone (4 mL) was heated at 75 C for 16 h. The reaction mixture was cooled to room temperature; the white precipitate was collected by filtration and solid was washed with acetone. The solid was suspended in aqueous ammonia solution (10 ml.) and stirred for 2 h. The free base was collected by filtration and solid was washed with water, dried under reduced pressure to yield 2-(5-bromo-2,4-dimethoxyphenyl)-7-(pyrrolidin-1-yl)imidazo[1,2-a]pyridine 9a (51 mg, 35%) as an off-white solid. 1H NMR (300 MHz, CDCl3): delta 8.55 (s, 1H), 7.83 (d, J = 7.4 Hz, 1H), 7,80 (s, 1H), 6.55 (s, 1H), 6,43 (d, J = 2.2 Hz, 1H), 6.33 (dd, J = 2,2, 7,4 Hz, 1H), 3 ,99 (s, 3H), 3 ,94 (s, 3H), 3.40-3,30 (m, 4H), 2.10-2.00 (m, 4H); HPLC (Method 2) >99% (AUC), tR= 19.12 min: APCI MS m/z 404 [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,722550-01-8, its application will become more common.

Reference:
Patent; ONCOTHERAPY SCIENCE, INC.; MATSUO, Yo; HISADA, Shoji; NAKAMURA, Yusuke; CHAKRABARTI, Anjan; RAWAT, Manish; RAI, Sanjay; SATYANARAYANA, Arvapalli, Venkata; DUAN, Zhiyong; TALUKDAR, Arindam; RAVULA, Srinivas; DECORNEZ, Helene; (491 pag.)WO2017/58503; (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. 100848-70-2, name is 2-Methoxy-4-methylpyridine, the common compound, a new synthetic route is introduced below. HPLC of Formula: C7H9NO

(a); 9.2 g (69 mmol) of N-chlorosuccinimide was charged to a N,N-dimethylformamide (DMF) 15 ml solution of 8.0 g (65 mmol) of 2-methoxy-4-methylpyridine, followed by stirring for 18 hours. Water was added to the reaction solution, and the aqueous layer was extracted with diethyl ether. The organic layer was washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate and subjected to filtration, and the solvent was distilled off under reduced pressure. The crude product was purified by silica gel column chromatography to obtain 8.5 g (yield: 82%) of 5-chloro-2-methoxy-4-methylpyridine (melting point 32 to 33C). 1HNMR(CDCl3, 300 MHz): delta 2.32(s, 3H), 3.89(s, 3H), 6.62(s, 1H), 8.05(s, 1H)

The synthetic route of 100848-70-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1679003; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 212268-12-7, 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 212268-12-7, name is 2-Amino-3-nitro-5-fluoropyridine. This compound has unique chemical properties. The synthetic route is as follows.

(Reference Example 2-2) 5-Fluoro-3-nitropyridine-2-amine (2.66 g) suspended in concentrated hydrochloric acid (35 ml) was cooled to -15C, and an aqueous solution (7 ml) of sodium nitrite (2.57 g) was added dropwise over 10 minutes. After stirring at -10C for 1 hour, and further stirring at room temperature for 1 hour, under ice cooling a 30% aqueous sodium hydroxide solution was added for neutralization. The insolubles were collected by filtration, washed with water, air-dried, and then redissolved in ethyl acetate, before the insolubles were filtered off. The filtrate was concentrated under reduced pressure to afford 2-chloro-5-fluoro-3-nitropyridine (1.41 g). 1H NMR (400 MHz, CDCl3) delta: 8.03 (dd, 1H, J = 6.6, 2.7 Hz), 8.55 (d, 1H, J = 2.7 Hz).

According to the analysis of related databases, 212268-12-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Daiichi Sankyo Company, Limited; EP2471792; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 29681-45-6 ,Some common heterocyclic compound, 29681-45-6, molecular formula is C8H9NO2, 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.

To a solution of methyl 5-methylnicotinate (5 g, 33 mmol) in carbon tetrachloride (200 mL) was added NBS (5.9 g, 1 equiv) and dibenzoyl peroxide (1.2 g, 0.15 equiv). The reaction was refluxed for 3 h, then was cooled to RT to give compound 14A. The carbon tetrachloride solution containing compound 14A was used without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,29681-45-6, its application will become more common.

Reference:
Patent; Li, James J,; Hamann, Lawrence G.; Ruan, Zheming; Cooper, Christopher B.; Wu, Shung C.; Simpkins, Ligaya M.; Wang, Haixia; Nayeem, Akbar; Krystek, Stanley R.; US2006/235028; (2006); 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. 1079179-12-6, name is 2-Chloro-3-fluoro-5-nitropyridine, the common compound, a new synthetic route is introduced below. name: 2-Chloro-3-fluoro-5-nitropyridine

To a stirred solution of 2-chloro-3-fluoro-5-nitropyridine (1.6 g, 9.0 mmol) in tetrahydrofuran (16 mL) was added tributylvinyltin (3.42 g, 10.8 mmol) and Pd2(dba) 3 (0.42 g, 0.45 mmol), trifuryl phosphene (0.2 g, 0.9 mmol) under nitrogen atmosphere. The reaction mixture was deoxygenated thoroughly and was heated to 60 C for 6 h. The reaction mixture was diluted with water (20 mL) and was extracted with ethyl acetate (3 x 25 mL). The combined organic layer was washed with brine (25 mL) and dried over anhydrous magnesium sulfate and concentrated under reduced pressure to afford the crude compound. The crude compound was purified by column chromatography (silica gel: 100-200 mesh; eluent: 5 % ethyl acetate in hexane) to afford 3-fluoro-5-nitro-2-vinylpyridine. (1.5 g, 96 %).

The synthetic route of 1079179-12-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GRUeNENTHAL GMBH; FRANK, Robert; CHRISTOPH, Thomas; LESCH, Bernhard; LEE, Jeewoo; WO2013/13817; (2013); 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. 188637-63-0, name is (6-Bromopyridin-2-yl)methanamine, molecular formula is C6H7BrN2, 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. Formula: C6H7BrN2

General procedure: Additional amide analogs were prepared by adding 1.5 equivalents of an amine which will provide the desired substituents into a 1 dram vial (1.5 eq.) along with lithium 5-amino-7- methoxyimidazo[1,2-c]quinazoline-2-carboxylate (30 mg, 0.114 mmol) and a DMF solution (1.0 ml) solution of DIPEA (0.079 ml, 0.454 mmol), shaking the vial for 5 minutes in a Bohdan Miniblock Shaker and then adding 1-propanephosphonic acid cyclic anhydride (50% w/w in EtOAc, 64.7 mul, 0.109 mmol), and continuing to shake the vial at RT overnight. The completed reaction was quenched with 1.0 ml water and the organic layer separated by filtering through a Varian 2 ml Reservior Frit and a Whatman 0.45mum syringe filter to remove emulsion, followed by solvent removal using a Genevac. The crude residue was dissolved in 1.0 ml DMSO and purified by LC/MS.

With the rapid development of chemical substances, we look forward to future research findings about 188637-63-0.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ALI, Amjad; LIM, Yeon-Hee; GALLO-ETIENNE, Gioconda, V.; KELLY, Joseph, Michael; BERLIN, Michael; TING, Pauline; TAGAT, Jayaram, R.; XIAO, Dong; KUANG, Rongze; WU, Heping; WANG, Hongwu; (157 pag.)WO2019/118313; (2019); 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. 1060814-91-6, name is Ethyl 2-(4-bromopyridin-2-yl)acetate. A new synthetic method of this compound is introduced below., Formula: C9H10BrNO2

To a solution of compound 5-7 (2 g, 8.19 mmol, 1 eq) in dimethylformamide (20 mL) was added sodium hydride (819 mg, 20.48 mmol, 60% purity in mineral oil, 2.5 eq) at 0C and the mixture was stirred at 20C for 30 minutes. The mixture was cooled to 0C and then compound 5-8 (1.69 g, 9.01 mmol, 680.02 uL, 1.1 eq) was added. The mixture was stirred at 20C for 1 hour. TLC indicated the starting material was consumed completely and a new spot formed. The mixture was poured into water (20 mL) and extracted with ethyl acetate (20 mLx3). The combined organic phase was washed with brine (20 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford compound 5-9 (1 g, 3.11 mmol, 37.90% yield, 83.88% purity) as yellow oil. LCMS: RT = 0.722 min, purity: 83.88%, m/z 269.9, 271.9 [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, 1060814-91-6, Ethyl 2-(4-bromopyridin-2-yl)acetate.

Reference:
Patent; SLOAN-KETTERING INSTITUTE FOR CANCER RESEARCH; TRI-INSTITUTIONAL THERAPEUTICS DISCOVERY INSTITUTE, INC.; FUSHIMI, Makoto; SCALTRITI, Maurizio; HELLER, Daniel, Alan; MONTERRUBIO MARTINEZ, Carles; ARRUABARRENA ARISTORENA, Amaia; MEINKE, Peter, T.; FOLEY, Michael, Andrew; ASANO, Yasutomi; ASO, Kazuyoshi; TAKAHAGI, Hiroki; SHAMAY, Yosef; BASELGA TORRES, Jose, Manuel; SASAKI, Yusuke; MICHINO, Mayako; (271 pag.)WO2020/72892; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 89364-04-5, 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. 89364-04-5, name is 3-Bromo-4-nitropyridine, molecular formula is C5H3BrN2O2, 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.

Example 1 (0052) Non-radioactive fluorination of 3-bromo-4-nitropyridine (3): 10 muL of 1 M tetrabutylammonium fluoride (TBAF) solution in THF (10 mumol, 0.5 eq.) was added to a solution of 3-bromo-4-nitropyridine (96%, Aurum Pharmatech, LLC) (20 mumol, 1 eq.) in 500 L of anhydrous dimethylsulfoxide (DMSO) in a 2 mL HPLC vial. The reaction was analyzed by HPLC (conditions A). Retention times: 3-bromo-4-nitropyridine (3)=10.83 min, 3-fluoro-4-nitropyridine=8.38, 3-bromo-4-fluoropyridine (6)=11.76 min. Retention times for the product matched within 0.05 min the reference standard. Identity of the product was confirmed by HR-MS (m/z M+ exp.: 174.9423, calc: 174.9433) and 1H, 13C and 19F NMR. Product amount was calculated from the area under the curve of the HPLC UV1 trace using a calibration curve.

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 89364-04-5, 3-Bromo-4-nitropyridine.

Reference:
Patent; The University of Chicago; Brugarolas, Pedro; (35 pag.)US2017/355648; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1026796-81-5, N-(4-Bromopyridin-2-yl)acetamide, 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, 1026796-81-5, blongs to pyridine-derivatives compound. HPLC of Formula: C7H7BrN2O

00569] Step 1: N-(4-bromopyridin-2-yl)-N-(4-methoxybenzyl)acetamide [00570] To a 20 mL vial charged with Sodium hydride (0.196 g, 7.76 mmol) was added dry N,N- Dimethylformamide (5.0 mL, 64 mmol), cooled with ice bath. N-(4-bromopyridin-2-yl)acetamide (1.50 g, 7.00 mmol) was added portionwise in ~ 3 min. The suspension was stirred at the same temperature for 15 min and turned into a clear solution. 4-methoxybenzyl bromide (1.55 g, 7.70 mmol) was added dropwise with a syringe and rinsed down with dry N,N-Dimethylformamide (2.0 mL, 26 mmol). The MPI09-013P1RNWOM PCT FILING mixture was stirred at r.t. for 17 hours. The mixture was poured into ice chilled saturated NaHCO3 (80 mL), extracted with EtOAc (2 x 100 mL), washed with water, brine, dried over anhydrous Na2SO4, filtered, evaporated in rotavpor to give a crude. Chromatograph using EtOAc/hexane (1/9 to 7/3) gave an oily product (1.80 g, yield 76.7%). LCMS: (AA) ES+, 335, 337. 1H NMR (400 MHz, d, -chloroform) delta:8.28-8.30 (d, J = 5.27 Hz, IH), 7.43 (s, IH), 7.31-7.33 (dd, J = 5.52, 1.51 Hz, IH), 7.13-7.15 (d, J = 8.78Hz, 2H), 6.80-6.82 (d, J = 8.78 Hz, 2H), 5.05 (s, 2H), 3.77 (s, 3H), 2.12 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1026796-81-5, its application will become more common.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; TAKEDA PHARMACEUTICAL COMPANY LIMITED; BANNO, Hiroshi; HIROSE, Masaaki; KURASAWA, Osamu; LANGSTON, Steven, P.; MIZUTANI, Hirotake; SHI, Zhan; VISIERS, Irache; VOS, Tricia, J.; VYSKOCIL, Stepan; WO2010/90716; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 133928-73-1, 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. 133928-73-1, name is 2-Chloro-3-methyl-4-pyridinecarboxylic Acid. A new synthetic method of this compound is introduced below.

[01652] Step 4: Synthesis of methyl 2-chl hylpyridine-4-carboxylate[01653] To a stirred solution of 2-chloro-3-methylpyridine-4-carboxylic acid (780 mg, 4.5 mmol) in anhydrous DMF (5.0 ml), was added potassium carbonate (1 .25 g, 9.1 mmol), followed by methyl iodide (0.42 ml, 6.8 mmol) dropwise. A further 4 ml of DMF was added and the reaction mixture was stirred at room temperature under nitrogen for 18.5 hours. The solvent was removed in-vacuo and the residue was then partitioned between CI b b (20 ml) and water (20 ml). The layers were separated and the aqueous layer was extracted with CH2C12 (3 x 15 ml). The combined organic layers were washed with water (2 x 30 ml), brine (40 ml), dried (MgS0 ), filtered and concentrated in-vacuo. The residue was purified by column chromatography (l Og SNAP cartridge, Isolera, 0-6% ethyl acetate:heptanes) to give the title compound (591 mg, 59%) as a colourless oil. LC-MS 84%, m/z = 185.9, 1 87.9; NMR (500 MHz, Chloroform-d) delta ppm 8.33 (d, J=5.04 Hz, 1 H) 7.54 (d, J=5.04 Hz, 1 H) 3.95 (s, 3 H) 2.60 (s, 3 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,133928-73-1, 2-Chloro-3-methyl-4-pyridinecarboxylic Acid, and friends who are interested can also refer to it.

Reference:
Patent; EPIZYME, INC.; EISAI CO., LTD.; KUNTZ, Kevin, Wayne; CHESWORTH, Richard; DUNCAN, Kenneth, William; KEILHACK, Heike; WARHOLIC, Natalie; KLAUS, Christine; ZHENG, Wanjun; WO2012/142513; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem