Category: pyridine-derivatives

Reference of 1594-58-7, Adding some certain compound to certain chemical reactions, such as: 1594-58-7, name is N-Hydroxynicotinimidamide,molecular formula is C6H7N3O, 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 1594-58-7.

General procedure: The newly synthesized acyl chloride dissolved intoluene (10 mL) was slowly added to a solution ofamidoxime (2.5 mmol) dissolved in toluene (40 mL) in a250 mL round-bottomed flask at 25 oC and under constantstirring. After the addition, the solution was refluxed for20 h, and then washed with sodium carbonate solution. Theorganic phase was dried with anhydrous sodium sulfateand thereafter the toluene was removed under vacuumby heating. A solid was obtained, which was purified byfash column chromatography using a hexane/ethyl acetatemixture as eluent with an increasing polarity gradient (9:1to 6:4).20

According to the analysis of related databases, 1594-58-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Cunha, Felipe S.; Nogueira, Joseli M. R.; De Aguiar, Alcino P.; Journal of the Brazilian Chemical Society; vol. 29; 11; (2018); p. 2405 – 2416;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 677728-92-6 ,Some common heterocyclic compound, 677728-92-6, molecular formula is C6H4FNO, 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.

l-(6-fluoropyridin-3-yl)prop-2-yn-l-yl acetate : 6-fluoronicotinaldehyde (300 mg, 2.40 mmol) was dissolved in THF (15 mL) and brought to 0 C. Ethynylmagnesium bromide (0.5 M in THF, 5.76 mL, 2.88 mmol) was added slowly and the resulting solution allowed to stir for 30 minutes. Acetic anhydride (0.45 mL, 4.80 mmol) was then added, the cold bath removed, and the reaction mixture allowed to warm to room temperature over 2 hours. The reaction contents were quenched by the addition of saturated aqueous NH4C1 (5 mL), poured into water (5 mL), and extract with EtOAc (3 x 15 mL). The combined organic phase was washed with brine (10 mL), dried over MgS04 and concentrated. The crude residue was purified by flash chromatography (eluent: EtOAc / hexanes) to give the desired product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,677728-92-6, its application will become more common.

Reference:
Patent; GILEAD SCIENCES, INC.; BACON, Elizabeth, M.; BALAN, Gayatri; CHOU, Chien-Hung; CLARK, Christopher, T.; COTTELL, Jeromy, J.; KIM, Musong; KIRSCHBERG, Thorsten, A.; LINK, John, O.; PHILLIPS, Gary; SCHROEDER, Scott, D.; SQUIRES, Neil, H.; STEVENS, Kirk, L.; TAYLOR, James, G.; WATKINS, William, J.; WRIGHT, Nathan, E.; ZIPFEL, Sheila, M.; (604 pag.)WO2017/7689; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 19524-06-2, 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. 19524-06-2, name is 4-Bromopyridine hydrochloride. A new synthetic method of this compound is introduced below.

Zinc bromide (502 g, 2.23 mole) was added in approximately 100 g portions to 2.0 L of tetrahydrofuran cooled to between 0 and 10°C. To this cooled solution was added 4- bromopyridine hydrochloride (200 g, 1.02 mol), triphenylphosphine (54 g, 0.206 mol), and palladium (II) chloride (9.00 g, 0.0508 mol). Triethylamine (813 g, 8.03 mol) was then added at a rate to maintain the reaction temperature at less than 10°C, and finally trimethylsilylacetylene (202 g, 2.05 mol) was added. The mixture was heated to 60°C for 4.5 hours. The reaction was cooled to -5°C and combined with 2.0 L of hexanes and treated with 2 L of 7.4 M NH4OH. Some solids were formed and were removed as much as possible with the aqueous phase. The organic phase was again washed with 2.0 L of 7.4 M NH4OH, followed by 2 washes with 500 mL of water, neutralized with 1.7 L of 3 M hydrochloric acid, dried with sodium sulfate, and concentrate to a thick slurry. The slurry was combined with 1.0 L of hexanes to give a precipitate. The precipitate was removed by filtration and the filtrate was concentrated to 209 g of dark oil. The product was purified by distillation (0.2 torr, 68°C) to give 172 g (96percent) of Compound (VI) as colorless oil. Analytical data: NMR (500 MHz, DMDO-de) delta 8.57 (2 H), 7.40 (2 H), 0.23 (9 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,19524-06-2, its application will become more common.

Reference:
Patent; ELI LILLY AND COMPANY; KOPACH, Michael, E.; WILSON, Thomas, Michael; KOBIERSKI, Michael, Edward; (35 pag.)WO2017/31215; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 76006-08-1, 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. 76006-08-1, name is 5-Chloro-1H-pyrazolo[3,4-c]pyridine, molecular formula is C6H4ClN3, 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.

5-bromo-2-methyl-2H-indazole (515 mg, 2.44 mmol) and (0404) bis[(tetrabutylammonium iodide)copper(I) iodide] (456 mg, 0.407 mmol) were combined in a reaction vessel, followed by5-chloro-lH-pyrazolo[3,4-c]pyridine (250 mg, 1.628 mmol), trans- N,N’-dimethylcyclohexane-l,2-diamine (0.257 ml, 1.628 mmol), and anhydrous K3P04 (691 mg, 3.26 mmol). This mixture was then evacuated and backfilled with N2 (3 times). Anhydrous degassed dioxane (20 ml) was added to this flask. This mixture was again evacuated and backfilled with N2 (3 times) and then as heated at 110C for 22h. LCMS showed a peak consistent with product. The reaction was diluted with EtOAc and water. The blue colored aqueous layer was separated from the green colored organic layer. The aqueous layer was extracted with EtOAc. The combined organics were filtered and concentrated. The residue was purified by column chromatography on silica gel (24g), eluting with 1-100 % EtOAc/hexanes to give 5-chloro-l-(2-methyl-2H-indazol-5-yl)-lH-pyrazolo[3,4-c]pyridine LCMS: M+H = 284

According to the analysis of related databases, 76006-08-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; SILIPHAIVANH, Phieng; METHOT, Joey; LIPFORD, Kathryn Ann; MOLINARI, Danielle; SLOMAN, David, L.; WITTER, David; ZHOU, Hua; BOYCE, Christopher; HUANG, Xianhai; LIM, Jongwon; GUERIN, David; KARUNAKARAN, Ganesh Babu; BAKSHI, Raman Kumar; LIU, Ziping; FU, Jianmin; WAN, Zhilong; LIU, Wei; (216 pag.)WO2016/100050; (2016); 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 113118-81-3, name is 5-Bromonicotinaldehyde. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C6H4BrNO

General procedure: To a solution of the proper bromopyridine-carbaldehyde (VI, 1 eq.) in MeOH, NaBH4 (2 eq.) was added portionwise. The mixture was stirred at room temperature for 3 hours. After this time, water was added and the mixture was concentrated under vacuum. The residue was diluted with water and extracted with DCM. The combined organic phases were dried over anhydrous MgS04, filtered and evaporated under reduced pressure to give the intermediate compound having general formula VII, which was used in the next step without further purification. (0151) (5-Bromopyridin-3-yl)methanol (Vila). The title compound was obtained according to general procedure B, step 1 using 5-bromopyridine-3-carbaldehyde (Via, 0.25 g, 1.34 mmol), NaBH4 (0.10 g, 2.69 mmol). The crude (0.15 g) was used in the next step without further purification. Yield = 60%.

With the rapid development of chemical substances, we look forward to future research findings about 113118-81-3.

Reference:
Patent; AZIENDE CHIMICHE RIUNITE ANGELINI FRANCESCO – A.C.R.A.F. S.P.A.; FURLOTTI, Guido; CAVARISCHIA, Claudia; BUONFIGLIO, Rosa; OMBRATO, Rosella; IACOANGELI, Tommaso; (61 pag.)WO2019/215075; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 52200-48-3, 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 52200-48-3 as follows.

Intermediate [Example Int22.13-bromo-2-ethoxypyridine3-Bromo-2-chloropyridine (10.0 g) was dissolved in ethanol (100 mL) and a solution of sodium ethylate in ethanol (70.8 mL, 21 %) was added. The mixture was heated to reflux overnight. The solvent was then removed in vacuo and the residue was dissolved in ethyl acetate and washed with satd. aqueous ammonium chloride solution. The organic layer was dried over sodium sulphate, and the solvent was evaporated. The crude product was purified by column chromatography on silica gel (eluent: cyclohexane / ethyl acetate 10: 1 ) to yield 7.26 g (69%) of an yellow oil.1 H-NMR (400MHz, DMSO-d6): delta [ppm]= 1 .34 (t, 3H), 4.37 (q, 2H), 6.93 (dd, 1 H), 8.02 (dd, 1 H), 8.15 (dd, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,52200-48-3, its application will become more common.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; KOPPITZ, Marcus; SCHULZE, Volker; KOSEMUND, Dirk; SCHIROK, Hartmut; BADER, Benjamin; LIENAU, Philipp; MARQUARDT, Tobias; WEGSCHEIDT-GERLACH, Christof; SIEMEISTER, Gerhard; PRECHTL, Stefan; WENGNER, Antje; BOeMER, Ulf; WO2011/64328; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 17228-69-2, 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. 17228-69-2, name is 2-Chloro-4-methoxypyridine. A new synthetic method of this compound is introduced below.

General procedure: To a round bottle flask containing 1 (2 mmol) was added methyl iodide (10 mmol; 5 equiv.) and the mixture was stirred at room temperature or refluxed overnight. The reaction was monitored by TLC. After completion, the resulting precipitate was separated by filtration and purified by recrystallization.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,17228-69-2, its application will become more common.

Reference:
Article; Yi, Xiao; Chen, Jing; Xu, Xiuling; Ma, Yongmin; Synthetic Communications; vol. 47; 9; (2017); p. 872 – 877;,
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 170850-45-0, name is 6-(p-Tolyl)pyridin-3-amine. This compound has unique chemical properties. The synthetic route is as follows. category: pyridine-derivatives

General procedure: 4.4.1 N-(4′-Methylbiphenyl-4-yl)acetamide 6b. Compound 4a (0.33 mmol, 60 mg), 5b (0.70 mmol, 1.104 g mL-1, 50 muL), PS-NMM (0.70 mmol, 175 mg) and CH2Cl2 (10 mL) were stirred at rt for 48 h. The mixture was filtered and the filtrate was concentrated under reduced pressure. The crude product was purified by chromatography on silica gel, CH2Cl2/EtOAc 9:1, to give 77 mg of the pure expected product as an off-white solid (99% yield).

With the rapid development of chemical substances, we look forward to future research findings about 170850-45-0.

Reference:
Article; Baltus, Christine B.; Press, Neil J.; Antonijevic, Milan D.; Tizzard, Graham J.; Coles, Simon J.; Spencer, John; Tetrahedron; vol. 68; 45; (2012); p. 9272 – 9277;,
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. 66572-56-3, name is 2-Bromoisonicotinic acid, molecular formula is C6H4BrNO2, 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. Recommanded Product: 66572-56-3

To a solution of 2-bromoisonicotinic acid (1.87 g, 9.26 mmol), 1H-imidazole (573mg, 8.42 mmol) and Cs2C03 (6.03 g, 18.5 mmol) in DMSO (18.6 mL), was added Cui (176mg, 0.926 mmol). The mixture was heated to 125C, stirred for 18 hours, cooled to room10 temperature, filtered and purified by preparative HPLC (1 0-90% acetonitrile in water) to givethe title compound as a light pink solid (1. 72 g, 98% ). MS 190 (MH+).

With the rapid development of chemical substances, we look forward to future research findings about 66572-56-3.

Reference:
Patent; SENOMYX, INC.; TACHDJIAN, Catherine; KARANEWSKY, Donald; WERNER, Sara; DARMOHUSODO, Vincent; YAMAMOTO, Jeff; WO2014/25706; (2014); 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. 33252-63-0, name is 5-(Trifluoromethyl)pyridin-2-ol. A new synthetic method of this compound is introduced below., Safety of 5-(Trifluoromethyl)pyridin-2-ol

V-bromosuccinimide (NBS, 39.0Og, 0.22 mol) is added portionwise to a solution of 5- {trifluoromethyl)pyridin-2-ol (30.0Og, 0.18 mol) in DMF (180 ml_), and the resulting mixture is stirred for 2 hours. The mixture is poured into water (1200 ml.) and the precipitate is collected by filtration. The crystal is dried in vacuo to give the product as a white solid (1st crystal : 28.1Og). The filtrate is extracted with EtOAc, and the organic layer is concentrated. The residue is poured into water and the precipitate is collected by filtration. The crystal is dried in vacuo to give 3-bromo-5-(trifluoromethyl)pyridin-2-ol as a yellow solid. 1H-NMR (400MHz, CDCI3), delta (ppm): 7.86 (d, 1 H), 8.02 (d, 1 H), 13.17 (br, 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, 33252-63-0, 5-(Trifluoromethyl)pyridin-2-ol.

Reference:
Patent; NOVARTIS AG; WO2008/58961; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem