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.956010-87-0, name is 3-(Trifluoromethyl)-1H-pyrazolo[3,4-b]pyridine, molecular formula is C7H4F3N3, molecular weight is 187.12, as common compound, the synthetic route is as follows.Quality Control of 3-(Trifluoromethyl)-1H-pyrazolo[3,4-b]pyridine

To compound 12 (150 mg, 0.80 mmol) and benzene-1,2-diamine (104 mg, 0.96 mmol) was added a 1N aqueous sodium hydroxide solution (3.0 mL), and the mixture was heated in a microwave oven to 150 C for 10 min. The mixture was diluted with water and extracted twice with ethyl acetate. The solvent was evaporated, and the residue was purified by preparative HPLC to yield 80 mg (42 %) of the title compound as a white solid. 1H NMR (400MHz, DMSO-d6): delta 7.19-7.29 (m, 2H), 7.39 (dd, J=8.1, 4.4Hz, 1H), 7.53 (d, J=7.1Hz, 1H), 7.74 (d, J=7.1Hz, 1H), 8.65 (dd, J=4.4, 1.0Hz, 1H), 8.85 (dd, J=7.8, 1.0Hz, 1H), 13.12 (br s, 1H), 14.19 (br s, 1H). 13C NMR (125 MHz, DMSO-d6): delta 111.5, 112.8, 118.2, 119.0, 121.6, 122.9, 131.3, 134.2, 135.6, 143.8, 146.5, 149.7, 152.7. HRMS m/z calcd for C13H9N5 + [H+]: 236.0931; found: 236.0936.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,956010-87-0, 3-(Trifluoromethyl)-1H-pyrazolo[3,4-b]pyridine, and friends who are interested can also refer to it.

Reference:
Article; Schirok, Hartmut; Griebenow, Nils; Fuerstner, Chantal; Dilmac, Alicia M.; Tetrahedron; vol. 71; 34; (2015); p. 5597 – 5601;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1093879-46-9 ,Some common heterocyclic compound, 1093879-46-9, molecular formula is C7H6BrNO2, 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 mixture of 2-(6-bromo-2-pyridyl)acetic acid (500 mg, 2.31 mmol) and ethyl 2- amino-2-methyl- propanoate (426 mg, 2.55 mmol, CAS 17288-15-2) in DMF (10 mL) was added HATU (1.14 g, 3.01 mmol) and DIPEA (897 mg, 6.94 mmol). Then the mixture was stirred at 20 C for 12 hours. On completion, the reaction mixture was concentrated in vacuo. The residue was washed with water (50 mL) and extracted with ethyl acetate (3 X 50 mL). The organic layer was dried with Na2SO4, filtered and concentrated in vacuo. The residue was purified by prep-column chromatography (petroleum ether:ethyl acetate = 1:1) to give the title compound (580 mg, 76% yield) as a yellowish oil. LCMS: (ES+) m/z (M+H)+= 328.9, tR = 0.742

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1093879-46-9, its application will become more common.

Reference:
Patent; RAZE THERAPEUTICS, INC.; MAINOLFI, Nello; (215 pag.)WO2018/106636; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1003711-43-0 , The common heterocyclic compound, 1003711-43-0, name is 2-Bromo-5-hydroxy-3-methylpyridine, molecular formula is C6H6BrNO, 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.

0.49 g (6.82 mmoi) cyclopropane methanol in 10 mL THF are charged with 0.42 g (11.4 mmoi) NaH and the reaction mixture is stirred at r.t. for 20 min. Then 1.00 g (5.68 mmoi) 5-bromo-2-fluoropyridine are added and the mixture is stirred at r.t. over night. The reaction is quenched by the addition of water and extracted with EtOAc. The organic layers are combined, dried over MgS04l filtered and the solvent is removed in vacuo. The crude product is purified by HPLC (MeOH/H20/FA). CgH-ioBrNO (M= 228.1 g/mol) ESI-MS: 228/229 [M+H]+ Rt (HPLC):1.14 min (method C) The following compounds are prepared analogously to example XXV.1 ; For example XXV.4 the reaction conditions are 50 C for 4 h. For examples XXV.10 – XXV.13 and XXV.19 – XXV.21 the reaction time is 2 h. For example XXV.9 no solvent is used and the reaction temperature is 95 C. For the examples XXV.4, XXV.10 – XXV.12, XXV.15 – XXV.16 and XXV.19 – XXV.21 the reaction is done in DMF. For example XXV.18 the reaction is done in DMSO at 100 C. For example XXV.21 toluene is used as solvent and the reaction conditions are 50 C for 1 h. For example XXV.22 methyltetrahydrofurane is used as solvent at 0 C for the deprotonation and 50 C for the substitution..

The synthetic route of 1003711-43-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; FLECK, Martin; HEINE, Niklas; NOSSE, Bernd; ROTH, Gerald Juergen; WO2014/114578; (2014); A1;,
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 40473-07-2, name is 2-Bromo-6-methoxypyridine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C6H6BrNO

To a solution of the compound of Preparation 113 (5.6 g, 29.8 mmol) in anhydrous tetrahydrofuran (100 ml), at -78° C. and under nitrogen, was added n-butyllithium (1.6M in hexane, 19.5 ml), via syringe. The mixture was stirred at -78° C. for 30 min, before addition of N,N-dimethylformamide (2.5 ml, 32.8 mmol). The reaction mixture was allowed to warm to room temperature and stirred for 18 h, before being acidified with sulphuric acid (2M) and then neutralised by addition of sodium hydrogen carbonate. The mixture was concentrated in vacuo and the residue was extracted with ethyl acetate (4*150 ml). The combined extracts were dried (MgSO4) and concentrated in vacuo to give the title compound (3.0 g). 1H-NMR (CDCl3): 4.01-4.05 (3H), 6.95-7.00 (1H), 7.54-7.58 (1H), 7.70-7.76 (1H), 9.95-9.98 (1H)

With the rapid development of chemical substances, we look forward to future research findings about 40473-07-2.

Reference:
Patent; PFIZER LIMITED; US2008/103130; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 19346-44-2, 2-Fluoro-3-nitro-5-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, Safety of 2-Fluoro-3-nitro-5-methylpyridine, blongs to pyridine-derivatives compound. Safety of 2-Fluoro-3-nitro-5-methylpyridine

3-Amino-2-fluoro-5-methylpyridine was prepared analogously from 2-fluoro-5-methyl-3-nitropyridine. This compound was obtained in 89 percent yield as white solid melting at 27-28.5 C. Elemental Analysis C6 H7 FN2 Calc.: %C, 57.1; %H, 5.59; %N, 22.2 Found: %C, 56.9, %H, 5.65; %N, 22.6 1 H NMR CDCl3: 7.2 (d, 1H); 6.8 (d, 1H); 3.7 (br, 2H); 2.1 (s, 3H); 13 C NMR CDCl3: 151.8 (d, J=229); 134.5 (d, J=12.6); 132.2 (d, J=3.9); 129.9 (d, J=28.7); 125.8 (d, J=5.3), 17.8.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,19346-44-2, 2-Fluoro-3-nitro-5-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; DowElanco; US5461161; (1995); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6515-09-9, 2,3,6-Trichloropyridine, 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, 6515-09-9, blongs to pyridine-derivatives compound. Recommanded Product: 6515-09-9

Experiment in a volume of 100 ml in the high-pressure reactor made of steel, will be 2, 3, 6-trichloro-pyridine 4g soluble in 36g tetrahydrofuran, then added with embodiment 2 of the method for preparing the loading of 1 wt % of Pd2+/GO the catalyst dosage is 200 mg, the hydrogen pressure is 4.5 MPa, the reaction temperature is 30 C, the reaction time is 22h, after the reaction is ended, direct sampling gas phase chromatographic detection, 2,3-dichloro pyridine conversion is 75.3%, selectivity of 85.0%. After the reaction, the reaction solution is filtered to remove the catalyst, the filtrate after evaporating solvent, crystallization and purification the nitrile is heavyafter the second grade the resulting residue, to obtain the product 2,3-dichloro-pyridine.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6515-09-9, its application will become more common.

Reference:
Patent; Zhejiang University; Wei, Zuojun; Chen, Yidong; (8 pag.)CN105418492; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 84539-34-4, Adding some certain compound to certain chemical reactions, such as: 84539-34-4, name is 4-Amino-3,5-dibromopyridine,molecular formula is C5H4Br2N2, 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 84539-34-4.

Into a 500-mL round-bottom flask, was placed 3,5-dibromopyridin-4-amine (5 g, 19.85 mmol, 1.00 equiv), dioxane (150 mL), water(l5 mL), 4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane (10.08 g, 59.99 mmol, 3.00 equiv), CS2CO3 (19.56 g, 60.03 mmol, 3.00 equiv), and Pd(dppf)Cl2 (1.46 g, 2.00 mmol) under an atmosphere of nitrogen. The resulting solution was stirred for 15 h at 90C in an oil bath, after which it was concentrated under vacuum. The residue thus obtained was applied onto a silica gel column with ethyl acetate/petroleum ether (1 :3). This resulted in 3.0 g (87%) of 3,5-bis(prop-1-en-2-yl)pyridin-4-amine as light yellow oil. LCMS of 3,5-bis(prop-1-en-2-yl)pyridin-4-amine (Method A): 175.1 [M+H]+, retention time 0.872 min.

According to the analysis of related databases, 84539-34-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS INFLAMMASOME RESEARCH, INC.; GLICK, Gary; ROUSH, William; VENKATRAMAN, Shankar; SHEN, Dong-Ming; GHOSH, Shomir; SEIDEL, Hans Martin; FRANCHI, Luigi; WINKLER, David Guenther; OPIPARI, Anthony William Jr.; KATZ, Jason; (468 pag.)WO2020/10140; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 54718-39-7, 2,5,6-Trichloronicotinic acid, 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, Product Details of 54718-39-7, blongs to pyridine-derivatives compound. Product Details of 54718-39-7

1,1 ?-Carbonyldiimidazole (40 g, 247 mmol) was added in portions to 2,5,6- trichloronicotinic acid (50.7 g, 224 mmol, Combi-Blocks, San Diego, Calif.) in THF (400 mE), allowing gas evolution to cease between addition. The resulting mixture was stirred for 5 mm and then was degassed with house vacuum and flushed with nitrogen. The resulting mixture was heated to 50 C. for 60 mm, then diluted with toluene (100 mE) and concentrated to half the initial volume. The resulting mixture was cooled to 0 C. and ammonium hydroxide (60 mE, 437 mmol) was added slowly via syringe. The reaction was stirred for 10 mm at it, diluted with EtOAc (200 mE) and washed with water (3×100 mE). The organic layer was dried over anhydrous Na2504 and concentrated in vacuo. The residue was suspended in 9:1 heptane/EtOAc (300 mE) and filtered. The filtered solids were collected and the remaining mother liquor was partially evaporated to half the initial volume, cooled to 0 C., and filtered. The two crops of filtered solids were combined to provide 2,5,6-trichloroni- cotinamide.

The synthetic route of 54718-39-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Amgen Inc.; LANMAN, Brian Alan; BOOKER, Shon; GOODMAN, Clifford; REED, Anthony B.; LOW, Jonathan D.; WANG, Hui-Ling; CHEN, Ning; MINATTI, Ana Elena; WURZ, Ryan; CEE, Victor J.; (88 pag.)US2019/77801; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1196152-34-7 ,Some common heterocyclic compound, 1196152-34-7, molecular formula is C6H7BrN2O, 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.

[00237] A solution of 5-bromo-2,3-dihydro-benzo[1,4]dioxine (1.0 eq, 4.65 mmol), PdCl2(dtbpf) ([1, 1 ‘-bis(di-fe/f-butylphosphino)ferrocene] dichloropalladium(ll)) (0.1 eq, 0.46 mmol), KOAc (2.5 eq, 1 1.6 mmol), and bis(pinacolato)diboron (1.5 eq, 10.2 mmol) in dioxane (10 ml_) was purged with N2 for 10 min and the mixture was heated to 120 C for 3 h. Then, 2-bromo-6-methoxy-pyridin-4-amine (1.0 eq, 4.65 mmol), Pd(PPh3)4 (0.1 eq, 0.46 mmol), K2CO3 (2.0 eq, 9.30 mmol) and H2O (1 ml_) were added. The reaction was purged with N2 for 10 min and the mixture was heated to 110 C for 2.5 h. the mixture was cooled to RT then the solvent was removed. The dark residue was dissolved in ethyl acetate and filtered over celite. The compound in this organic layer was directly washed with water, brine, dried over magnesium sulphate, filtered and the reaction was concentrated in vacuo. The compound was purified by column chromatography eluting with dichloromethane then increasing the polarity with 0-5 % MeOH. Then the compound was purified by preparative HPLC-MS to afford 2-(2,3- dihydro-1,4-benzodioxin-5-yl)-6-methoxy-pyridin-4-amine (780 mg, 65 %) as a white solid. AnalpH2_MeOH_QC_V1, Rt: 3.93 min, m/z 259.3 [M+H]+ AnalpH9_MeOH_QC_V1, Rt: 6.46 min, m/z 259.3 [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,1196152-34-7, its application will become more common.

Reference:
Patent; OXFORD UNIVERSITY INNOVATION LIMITED; RABBITTS, Terrence; QUEVEDO, Camilo; CRUZ, Abimael; PHILIPS, Simon; FALLON, Philip Spencer; DUNN, Jonathan Neil; FREEM, Joshua Robert; LEE, Lydia Yuen-Wah; TRAORE, Tenin; WILLIAMS, Sophie Caroline; (219 pag.)WO2019/145718; (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. 914942-88-4, name is tert-Butyl (6-amino-7-iodo-1-methyl-1H-imidazo[4,5-c]pyridin-4-yl)(methyl)carbamate. A new synthetic method of this compound is introduced below., Formula: C13H18IN5O2

A suspension of Al.12 (1.0 g, 248 tnmol) in DMF (6.80 mL) was degassed by bubbling argon through the solvent. Phenylacetylene was added (0.68 mL, 6.2 mmol), followed by dichlorobis(triphenyl-phosphine)palladium II (0.10 g, 0.149 mmol), copper (I) iodide (28.4 mg, 0.06 mmol), and degasssed diisopropylamine (9.2 mL). The pressure tube was sealed and immediately immersed in a 60 0C oil bath, and stirred for 30 min. The reaction mixture was evaporated to dryness under vacuum. The crude product was partitioned between EtOAc (45 mL) and water. After separation, the EtOAc layer was washed with water, brine, dried (NaOSO4), and concentrated under reduced pressure to yield over 1.0 g of a brown taffy. Flash chromatography on silica gel, eluting with a hexane : EtOAc gradient yielded 0.94 g, (98%) of Al.13 as a pale yellow powder. HPLC (condition C): 92.9%, ret. Time 2.91 min., LC/MS (M+H)+ – 378.4.

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, 914942-88-4, tert-Butyl (6-amino-7-iodo-1-methyl-1H-imidazo[4,5-c]pyridin-4-yl)(methyl)carbamate.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2006/122137; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem