Category: pyridine-derivatives

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.5975-12-2, name is 2,4-Dichloro-3-nitropyridine, molecular formula is C5H2Cl2N2O2, molecular weight is 192.9876, as common compound, the synthetic route is as follows.category: pyridine-derivatives

Example 23Preparation of 7-(4-amino-2-(6-chlorobenzo[d][1,3]dioxol-5-ylthio)-1H-imidazo[4,5-c]pyridin-1-yl)-N-hydroxyheptanamide (Compound 34)Step 23a. 2-Chloro-N-(4-methoxybenzyl)-3-nitropyridin-4-amine (Compound 602); To a stirred solution of compound 601 (1 g, 5.18 mmol) in DMF (8.6 mL) was added (4-methoxyphenyl)methanamine (0.71 g 5.18 mmol) and triethylamine (0.644 mL). The reaction mixture was stirred at room temperature for 2 h. The mixture was evaporated to remove DMF and purified by column chromatography on silica gel (EtOAc/petroleum at 10:1) to obtain 602 as a yellow solid (1.32 g, 87%): LCMS: 294 [M+1]+; 1H NMR (DMSO-d6): delta 3.72 (s, 3H), 4.40 (d, 2H, J=6.3 Hz), 6.81 (d, 1H, J=5.7 Hz), 6.91 (d, 2H, J=9.0 Hz), 7.25 (d, 2H, J=8.4 Hz), 7.95 (d, 1H, J=5.4 Hz), 8.02 (t, 1H, J=5.7 Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5975-12-2, 2,4-Dichloro-3-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; Qian, Changgeng; Cai, Xiong; Gould, Stephen; Zhai, Haixiao; US2008/234297; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 779345-37-8, 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. 779345-37-8, name is 5-Fluoro-2-nitropyridine. A new synthetic method of this compound is introduced below.

To a solution of compound 73 (564 mg, 4.2 mmol, 1.2 eq) in dimethylacetamide (5 mL) at 0 C under nitrogen was added potassium tert-butoxide (513 mg, 4.6 mmol, 1.3 eq) portion wise. The mixture was stirred at 0 C for 1 h, and then a solution of compound 61 (500 mg, 3.5 mmol, 1.0 eq) in DMA (2 mL) was added portion wise. After addition, the reaction mixture was stirred at RT overnight. The reaction was quenched by water (15 mL) and extracted with EA (3 X 5 mL), dried over Na2S04, filtered and concentrated to give a crude residue (700 mg crude), which was used into next step without further purification. *H NMR (300 MHz, CDCb): delta 8.34-8.31 (m, 2 H), 7.72 (dd, J = 3.0 Hz, 9.0 Hz, 1 H), 4.07 (d, J = 6.0 Hz 2 H), 2.80- 2.76 (m, 2 H), 2.15 (s, 3 H), 1.89-1.81 (m, 2 H), 1.75-1.71 (m, 2 H), 1.37-1.23 (m, 3 H). LCMS: (M+H)+ = 252.2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,779345-37-8, its application will become more common.

Reference:
Patent; BEIJING XUANYI PHARMASCIENCES CO., LTD.; SONG, Yuntao; CHEN, Xiaoqi; (188 pag.)WO2019/35008; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 884495-36-7, Adding some certain compound to certain chemical reactions, such as: 884495-36-7, name is 6-Chloro-2-methylnicotinaldehyde,molecular formula is C7H6ClNO, 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 884495-36-7.

A mixture of 6-chloro-2-methylpyridine-3-carboxaldehyde (3.00 g, 19.3 mmol), A- mercaptophenol (90% pure, 2.7Og, 19.3 mmol) and K2CO3 (1.66 g, 12.0 mmol) in DMF (20 mL) was stirred at room temperature for 16 h. Bromoacetic acid tert-butyl ester (6.00 g, 30.8 mmol) and K2CO3 (3.40 g, 24.6 mmol) were added, and the mixture was stirred for another 4 h. Aqueous work-up and purification by flash chromatography on silica gel (EtOAc/hexanes, 1 :4 in v/v) afforded 4-(5-fo?nyl~6-methyl-rhoyridin-2-ylsulfanyl)-benzoic acid tert-butyl ester as EPO a pale yellow solid (7.40 g, 100%). 1H NMR (CDCl3) delta 1.50 (s, 9H), 2.81 (s, 3H)5 4.57 (s, 2H), 6.66 (d, IH, J= 8.1 Hz), 6.97-7.01 (m, 2H), 7.51-7.55 (m, 2H), 7.79 (d, IH, J= 8.1 Hz), 10.19 (s, IH).

According to the analysis of related databases, 884495-36-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ANORMED INC.; WO2007/22371; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 19798-81-3, name is 6-Bromopyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows. category: pyridine-derivatives

To a solution of 6-bromopyridin-2-amine (1 g, 5.78 mmol) in acetonitrile (10 mL) was added N-chlorosuccinimide (0.849 g, 6.36 mmol) and the mixture was heated at 80C for 12 hours. The mixture was filtered through diatomaceous earth and concentrated and the residue was dissolved in ethyl acetate and washed with water and brine. Drying over anhydrous sodium sulfate, filtration, concentration and purification by column chromatography (silica gel, 30% ethyl acetate in hexane) afforded the title compound. LCMS: 209.1 (M+2)+.

With the rapid development of chemical substances, we look forward to future research findings about 19798-81-3.

Reference:
Patent; ABBVIE INC.; ABBVIE PHARMACEUTICAL TRADING (SHANGHAI) CO., LTD.; TONG, Yunsong; BRUNCKO, Milan; CLARK, Richard F.; CURTIN, Michael L.; FLORJANCIC, Alan S.; FREY, Robin R.; GONG, Jianchun; HANSEN, Todd M.; JI, Zhiqin; LAI, Chunqiu; MASTRACCHIO, Anthony; MICHAELIDES, Michael; MIYASHIRO, Juliem; RISI, Roberto M.; SONG, Xiaohong; TAO, Zhi-fu; WOODS, Keith W.; ZHU, Guidong; PENNING, Thomas; SOUERS, Andrew; GOSWAMI, Rajeev; IQUTURI, Omprakash Reddy; DABBEERU, Madhu Babu; WO2014/139328; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.175965-83-0, name is 2-Fluoro-4-methoxypyridine, molecular formula is C6H6FNO, molecular weight is 127.12, as common compound, the synthetic route is as follows.name: 2-Fluoro-4-methoxypyridine

Method Z Step l To a solution of F6 (40.0 mg, 0.098 mmol) and 2-fiuoro-4-methoxypyridine (25.0 mg, 0.197 mmol) in DMSO (2 mL) was added Cs2C03 (96.0 mg, 0.295 mmol). The mixture was stirred at 1 10 C for 1 h under microwave condition, and then quenched with water, extracted with EtOAc (25 mL x 4). The combined extracts were washed with brine, dried over Na2S04 and concentrated in vacuo. The residue was further purified by p-HPLC (TFA) to give Example 71.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,175965-83-0, 2-Fluoro-4-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DAI, Xing; CUMMING, Jared, N.; LIU, Hong; SCOTT, Jack, D.; (0 pag.)WO2016/85780; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 13534-90-2, 3,4-Dibromopyridine, 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, 13534-90-2, blongs to pyridine-derivatives compound. Computed Properties of C5H3Br2N

The titled compound was prepared by the reaction of 3,4-dibromopyridine (1.01 g, 4.26 mmol) with 4-nitrophenylboronic acid pinacol ester (1.06 g, 4.26 mmol) using cesium carbonate (2.07 g, 6.39 mmol) and [l, -bis(diphenylphosphino)ferrocene]dichloropalladium (II) (155 mg, 0.21 mmol) in a mixture of DMSO and water (20 mL, 3: 1) as per the procedure described in Step 1 of Intermediate 1 to yield 455 mg of the product; 1H NMR (300 MHz, CDC13) delta 7.33 (d, 7 = 4.8 Hz, 1H), 7.63 (d, 7 = 8.7 Hz, 2H), 8.35 (d, 7 = 8.7 Hz, 2H), 8.64 (d, 7 = 5.1 Hz, 1H), 8.89 (s, 1H) ; ESI-MS (m/z) 281 (M+2H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13534-90-2, its application will become more common.

Reference:
Patent; GLENMARK PHARMACEUTICALS S.A.; DAS, Sanjib; GHARAT, Laxmikant Atmaram; HARDE, Rajendra Laxman; SHELKE, Sandeep Yadunath; PARDESHI, Shailesh Ramesh; THOMAS, Abraham; KHAIRATKAR-JOSHI, Neelima; SHAH, Daisy Manish; BAJPAI, Malini; (181 pag.)WO2017/21879; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1123194-98-8 ,Some common heterocyclic compound, 1123194-98-8, molecular formula is C10H10BrN3O, 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.

Synthesis of (E)-3-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]acrylamide Triethylamine (52 ml) was added to a suspension of 6-bromo-2-methoxy-3-(4-methyl-1H-imidazol-1-yl)pyridine (49.8 g), tris(dibenzylideneacetone)dipalladium (0) (5.11 g), tri-o-tolylphosphine (3.41 g) and acrylamide (14.5 g) in N,N-dimethyl formamide (260 ml). The reaction solution was stirred at 100C for 50 minutes. The reaction solution was returned to room temperature and then filtered through celite. The filter cake was sequentially washed with N,N-dimethylformamide, methanol, a 50% N,N-dimethylformamide solution and N,N-dimethylformamide. The resulting filtrate was filtered through celite again, and the filtrate was concentrated under reduced pressure. Toluene was added to the residue, and the reaction solution was concentrated again. Toluene and a saturated sodium bicarbonate solution were added to the resulting residue, and the insoluble matter was collected by filtration. The resulting powder was dried under reduced pressure to obtain 42.96 g of the title compound. The property values of the compound are as follows. 1H-NMR (CDCl3) delta (ppm): 2.30 (d, J=0.8Hz, 3H), 4.07 (s, 3H), 5.57 (brs, 1H), 5.68 (brs, 1H), 6.98 (brs, 1H), 7.00 (d, J=15.2Hz, 1H), 7.06 (d, J=7.6Hz, 1H), 7.54 (d, J=7.6Hz, 1H), 7.56 (d, J=15.2Hz, 1H), 7.82 (d, J=1.2Hz, 1H). ESI-MS; m/z 259 [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. 1123194-98-8, 6-Bromo-2-methoxy-3-(4-methyl-1H-imidazol-1-yl)pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Eisai R&D Management Co., Ltd.; EP2181992; (2010); 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. 6980-08-1, name is 4-Chloro-3-nitropyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 4-Chloro-3-nitropyridin-2-amine

2-Amino-3-nitro-4-chloropyridine (967 mg, 5.59 mmol) was dissolved in isopropanol (20 mL) and DIPEA (1.85 mL, 11.18 mmol) was added followed by N-methylpiperazine (0.744) mL, 6.71 mmol). The mixture was reacted at 90 C. for 12 h. A large amount of gold solid was isolated by cooling and was filtered, washed with isopropyl alcohol and ether in that order, and dried in vacuo to give the title compound (1.21 g, yield 92%) as a golden yellow solid.

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, 6980-08-1, 4-Chloro-3-nitropyridin-2-amine.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Long Yaqiu; Cao Bin; (103 pag.)CN103570683; (2018); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 6200-60-8, Adding some certain compound to certain chemical reactions, such as: 6200-60-8, name is Imidazo[1,2-a]pyridine-3-carboxylic acid,molecular formula is C8H6N2O2, 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 6200-60-8.

To a solution of imidazo[1,2-a] pyridine-3-carboxylic acid (250 mg) in DMF (7 mL), EDCI (443 mg, 1.5 equiv.), HOBt (312 mg, 1.5 equiv.), DIPEA (805 muL, 3.0 equiv.) and compound 73 (404 mg, 1.0 equiv.) were added. The resulting mixture was stirred at R.T. overnight. The reaction mixture was diluted with AcOEt (15 mL), washed with HCl 1M (2*10 mL) and water (2*10 mL). Combined aqueous layers were saturated with NaHCO3 and extracted with AcOEt (2*10 mL). The combined organic layers were washed with brine, dried over MgSO4 and concentrated under reduced pressure. Purification by flash-chromatography (MeOH 2% to 5% in CH2Cl2) followed by preparative HPLC afforded the product as a white solid (9.3 mg, yield <5%). 1H-NMR (400 MHz, DMSO): 1.11-1.79 (m, 13H, 5*CH2 + CH3); 3.33 (q, J 7.0 Hz, 2H, N-CH2); 6.81 (dd, J 1.9 Hz, J 8.1 Hz, 1H, Ar); 6.90 (d, J 2.0 Hz, 1H, Ar); 7.20 (m, 1H, Ar); 7.55 (m, 1H, Ar); 7.75-7.78 (m, 2H, Ar); 8.56 (s, 1H, Ar); 9.36 (bs, 1H, NH); 9.47 (m, 1H, Ar). N-CH signal under water peak. M/Z (M+H)+ = 407. 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. 6200-60-8, Imidazo[1,2-a]pyridine-3-carboxylic acid, other downstream synthetic routes, hurry up and to see. Reference:
Patent; Domain Therapeutics; EP2210891; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 5349-17-7, 2-Bromo-1-(pyridin-4-yl)ethanone hydrobromide, 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, 5349-17-7, blongs to pyridine-derivatives compound. COA of Formula: C7H7Br2NO

(c) Preparation of [(2-chloro-6-nitrophenyl)methyl](4-(4-pyridyl)(1,3-thiazol-2-yl))amine.To a solution of N-({[(2-chloro-6-nitrophenyl)methyl]amino}thioxomethyl)benzamide (Step b) (1.22 g, 3.5 mmol) in 70% aqueous MeOH (50 ML) was added K2CO3 (567 mg, 4.1 mmol) and the reaction was heated to reflux.After 1.5 h, the reaction was cooled (40 C.) and 2-bromo-1-(4-pyridyl)ethan-1-one hydrobromide (992.4 mg, 3.5 mmol) was added.After 1.5 h, the reaction mixture was cooled to RT and purified by flash chromatography with hexanes:EtOAc:CH2Cl2:MeOH (9:1:0:0, 3:1:0:0, 1:1:0:0, 0:0:49:1) as eluant to afford an off-white amorphous solid. MS m/z: 347 (M+1); 345 (M-1). Calc’d for C15H11ClN4O2S-b 346.03.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5349-17-7, its application will become more common.

Reference:
Patent; Huang, Qi; Kaller, Matthew; Nguyen, Thomas; Norman, Mark H.; Rzasa, Robert; Wang, Hui-Ling; Zhong, Wenge; US2003/229068; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem