Category: pyridine-derivatives

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. 145901-11-7, name is 1H-Pyrrolo[2,3-b]pyridin-6-amine. A new synthetic method of this compound is introduced below., SDS of cas: 145901-11-7

General procedure: A mixture of substituted 2,4-dichloropyrimidine (1.0 equiv.), and substituted aniline (1.0-1.05 equiv.), and DIPEA (1.2 equiv.) in isopropanol (0.1 M) was stirred and heated at reflux. The reaction time, work-up, and product isolation procedure are described below.

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, 145901-11-7, 1H-Pyrrolo[2,3-b]pyridin-6-amine.

Reference:
Patent; H. LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE, INC.; SCHOeNBRUNN, Ernst; LAWRENCE, Nicholas J.; LAWRENCE, Harshani R.; (173 pag.)WO2020/51572; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 127356-26-7, 6-Methoxypyridine-3,4-diamine, 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 6-Methoxypyridine-3,4-diamine, blongs to pyridine-derivatives compound. Application In Synthesis of 6-Methoxypyridine-3,4-diamine

To a solution of 6-methoxypyridine-3,4-diamine (0.45 g, 3.23 mmol) in ethanol was added ethyl trifluoropyruvate (0.393 mL, 3.23 mmol). The reaction mixture was heated to reflux at 90 C. for 16 h. The volatiles were removed under reduced pressure. To the residue was added Pet-ether. The resultant solid was isolated via filtration and dried to afford 7-methoxy-3-(trifluoromethyl)pyrido[3,4-b]pyrazin-2-ol and 7-methoxy-2-(trifluoromethyl)pyrido[3,4-b]pyrazin-3-ol as mixture of regioisomer (0.37 g 46% yield). MS: MS m/z 246.2 (M++1).; A solution of 7-methoxy-3-(trifluoromethyl)pyrido[3,4-b]pyrazin-2-ol and 7-methoxy-2-(trifluoromethyl)pyrido[3,4-b]pyrazin-3-ol (0.37 g, 1.509 mmol) in POCl3 (5 mL) was heated to 100 C. for 2 h. The solvent was removed under reduced pressure and the residue was diluted with ice cold water. The aqueous solution was basified to pH ?9.0 by using sodium bicarbonate, then was extracted with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure to get crude compound. The crude compound was purified by silica gel chromatography using 10% ethyl acetate in Pet-ether to get 2-chloro-7-methoxy-3-(trifluoromethyl)pyrido[3,4-b]pyrazine (0.135 g, 0.435 mmol, 28.8% yield) and 3-chloro-7-methoxy-2-(trifluoromethyl)pyrido[3,4-b]pyrazine (0.035 g, 0.435 mmol, 4.8% yield) as yellow solids.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,127356-26-7, 6-Methoxypyridine-3,4-diamine, and friends who are interested can also refer to it.

Reference:
Patent; Bristol-Myers Squibb Company; Sun, Li-Qiang; Zhao, Qian; Renduchintala, Kishore V.; Sarkunam, Kandhasamy; Nagalakshmi, Pulicharla; Gillis, Eric P.; Scola, Paul Michael; (81 pag.)US9643999; (2017); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 153034-86-7, 2-Chloro-4-iodopyridine, 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, 153034-86-7, blongs to pyridine-derivatives compound. name: 2-Chloro-4-iodopyridine

General procedure: An oven dried Schlenk tube was purged with nitrogen and charged with 3-iodopyridine (0.875 mmol, 179.3 mg), BiPh3 (0.25 mmol, 110 mg), K3PO4 (1.5 mmol, 318 mg), Pd(OAc)2 (0.025 mmol, 5.6 mg), PPh3 (0.1 mmol, 26.2 mg) followed by dry DMF (3 mL) under nitrogen atmosphere. The reaction mixture was stirred in an oil bath at 90C for 1h. It was brought to rt, treated with water (10mL), and extracted with ethyl acetate (2×20 mL). The organic extract was treated with brine, dried over anhydrous MgSO4, and concentrated using rotary evaporator under the reduced pressure. The crude was subjected to silica gel column chromatography (5% EtOAc/Hexane) to obtain 3-phenylpyridine (1.1) as colorless oil (115 mg, 98%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,153034-86-7, its application will become more common.

Reference:
Article; Rao, Maddali L.N.; Dhanorkar, Ritesh J.; Tetrahedron; vol. 71; 2; (2015); p. 338 – 349;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 114-33-0 , The common heterocyclic compound, 114-33-0, name is N-Methylnicotinamide, molecular formula is C7H8N2O, 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.

General procedure: Complex 11 was prepared by the reaction of an acetonitrile solution of copper(II) acetate monohydrate (1mmol, 0.20g) with N-methylnicotinamide (2mmol, 0.27g) followed by addition of 2,5-dichlorobenzoic acid (2mmol, 0.38g). The reaction mixture was stirred until a blue product was precipitated (1day). The fine blue microcrystals were filtered off, washed with a small portion of water and dried at ambient temperature. The mother liquors obtained from filtration were left to crystallize. The blue crystals suitable for X-ray structure determination were separated after several days. Yield: 0.67g (85%).

The synthetic route of 114-33-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Hala?ka, Jozef; Lokaj, Jan; Jomova, Klaudia; R??i?kova, Zde?ka; Mazur, Milan; Moncol, Jan; Polyhedron; vol. 175; (2020);,
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. 7169-97-3, name is N-(5-Bromopyridin-2-yl)acetamide, the common compound, a new synthetic route is introduced below. SDS of cas: 7169-97-3

EXAMPLE 295 5-[3-(3,4,8,9-Tetrahydro-6-methoxy-3,3,8,8-tetramethylfuro[2,3-h]isoquinolin-1-yl)phenyl]-2-pyridinamine A solution of sodium carbonate (198 mg, 1.86 mmol) in water (1 mL) and tetrakis(triphenylphosphine)palladium(0) (55 mg, 0.0475 mmol) were added to a solution of N-(5-bromo-2-pyridinyl)acetamide (243 mg, 1.13 mmol) and 3-cyanophenylboronic acid (249 mg, 1.70 mmol) in 1,2-dimethoxyethane (2 mL) and ethanol (1 mL) and the mixture was stirred at 80 C for 15 hours. Water was poured into the reaction mixture, which was extracted twice with tetrahydrofuran. The combined organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The resultant crystals were washed with diethyl ether to obtain N-[5-(3-cyanophenyl)-2-pyridinyl]acetamide (205 mg, yield: 77%). 1H NMR (CDCl3) delta 2.25 (3H, s), 7.54-7.92 (5H, m), 8.02 (1H, br s), 8.32 (1H, d, J = 8.0 Hz), 8.48 (1H, d, J = 2.2 Hz).

The synthetic route of 7169-97-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1270577; (2003); 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. 581-45-3, name is 4-(Piperidin-4-yl)pyridine. A new synthetic method of this compound is introduced below., Product Details of 581-45-3

Following the procedure of Example 74 using 5,5-Dioxo-2-(4-nitrobenzoxy-carbonylamino)dibenzothiophene (Example 24) and the appropriate amine the following compounds were prepared.

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, 581-45-3, 4-(Piperidin-4-yl)pyridine.

Reference:
Patent; Block, Michael Howard; Donald, Craig Samuel; Brittain, David Robert; Foote, Kevin Michael; US2003/225097; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference 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 14; Preparation of 3-chloro-N-[(lS)-1-(4-chlorophenyl) ethyl]-5-(methoxymethoxy)-4-pyridine- carboxamide (Compound 179); Step A: Preparation of 3-chloro-5- (methoxymethoxy) pyridine; To a solution of 5-chloro-3-hydroxypyridine (Aldrich, 5 g, 39 mmol) in acetonitrile (60 mL) was added chloromethyl methyl ether (3.11 g, 39 mmol) followed by potassium carbonate (10.78 g). The mixture was heated at 60 C for 18 h and then diluted with water (100 mL). The aqueous layer was extracted with ethyl acetate (4 x 100 mL). The combined organic layers were dried (MgSO4), and the solvent was evaporated under reduced pressure to leave the title compound as a yellow oil (5.5 g). 1H NMR (CDC13) 8 3.49 (s, 3H), 5.30 (s, 2H), 7.42 (s, 1H), 8.26 (s, 1H), 8. 31 (s, 1H)

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

Reference:
Patent; E.I. DUPONT DE NEMOURS AND COMPANY; WO2005/70889; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1659-31-0, 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.1659-31-0, name is Dipyridin-2-yl carbonate, molecular formula is C11H8N2O3, molecular weight is 216.19, as common compound, the synthetic route is as follows.

Step 2 To a suspension of sodium hydride, 60% in mineral oil (0.652 g, 16.31 mmol) in THF (25 mL) was added 3,3-difluoro-2-methylbutan-2-ol (1.84 g, 14.82 mmol) at 0 C. After stirring 30 min, the solution was transferred to a solution of di(pyridin-2-yl) carbonate (3.20 g, 14.82 mmol) in THF (25 mL) through a cannula. The formed slurry was stirred at 0 C. for 30 min. The slurry was warmed to rt and stirred for 2 h. The reaction was diluted with EtOAc, washed with brine, dried over MgSO4, filtered, concentrated to give a residue that was purified by Biotage eluting with 10-50% EtOAc in hexanes to afford the desired product 3,3-difluoro-2-methylbutan-2-yl pyridin-2-yl carbonate (500 mg, 13.76%) as an oil that later crystallized to a white solid upon standing. 1H NMR (500 MHz, CHLOROFORM-d) delta 8.43 (ddd, J=4.9, 2.0, 0.7 Hz, 1H), 7.95-7.75 (m, 1H), 7.31-7.24 (m, 1H), 7.15 (dt, J=8.2, 0.8 Hz, 1H), 1.72 (s, 6H), 1.77-1.66 (m, 3H).

The chemical industry reduces the impact on the environment during synthesis 1659-31-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Bristol-Myers Squibb Company; Hiebert, Sheldon; Rajamani, Ramkumar; Sun, Li-Qiang; Mull, Eric; Gillis, Eric P.; Bowsher, Michael S.; Zhao, Qian; Meanwell, Nicholas A.; Renduchintala, Kishore V.; Sarkunam, Kandhasamy; Nagalakshmi, Pulicharla; Babu, P. V. K. Suresh; Scola, Paul Michael; US2013/115190; (2013); A1;,
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. 71902-33-5, name is 3,5-Difluoropyridine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 71902-33-5

Into a 500 ml reaction flask, 400 ml of dichloromethane and 113.3 g of m-chloroperoxybenzoic acid were successively introduced.Water bath insulation drop between 25-30 °CA mixed solution of 57.5 g of 3,5-difluoropyridine and 100 ml of dichloromethane.Continue to stir at 25-30 ° C until the system becomes cloudy.After the reaction, 50 ml of 60percent potassium hydroxide aqueous solution was added, and the mixture was stirred for 0.5 hours, and then left to stand for liquid separation.Extract 300 times with 300 ml of dichloromethane. The organic phases were combined, dried over anhydrous sodium sulfate and concentrated to give 58.8 g of product.98..6percent.

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, 71902-33-5, 3,5-Difluoropyridine.

Reference:
Patent; Zhejiang Xingyue Pharmaceutical Technology Co., Ltd.; Tang Yang; Xu Zhigang; Ying Lv; Hu Junbin; Chen Qingquan; (5 pag.)CN109336810; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 153034-78-7 ,Some common heterocyclic compound, 153034-78-7, molecular formula is C6H5FIN, 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 solution of diisopropylamine (4.3 mL, 30.5 mmol) in THF (50 mL) at -78 C. was treated with 2.5M n-butyllithium in hexanes (12.2 mL, 30.5 mmol), stirred for 30 minutes, treated dropwise with a solution of 2-fluoro-3-iodo-5-methylpyridine (7.24 g, 30.5 mmol) in THF (30 mL), stirred for 4 hours, quenched with water, and extracted with diethyl ether. The combined extracts were washed sequentially with Na2S2O3, water, and brine, dried (MgSO4), filtered, and concentrated to provide 6.3 g (87%) of the desired product. MS (DCI/NH3) m/z 238 (M+H)+; 1H NMR (CDCl3) delta 7.99 (s, 1H), 7.43 (d, 1H), 2.38 (m, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,153034-78-7, its application will become more common.

Reference:
Patent; Claiborne, Akiyo K.; Gwaltney, II, Stephen L.; Hasvold, Lisa A.; Li, Qun; Li, Tongmei; Lin, Nan-Horng; Mantei, Robert A.; Rockway, Todd W.; Sham, Hing L.; Sullivan, Gerard M.; Tong, Yunsong; Wang, Gary; Wang, Le; Wang, Xilu; Wang, Wei-Bo; US2002/115640; (2002); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem