Pyridine-derivatives

Electric Literature of 76015-11-7, 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. 76015-11-7, name is 3-Methoxy-2-methylpyridin-4(1H)-one. A new synthetic method of this compound is introduced below.

3-Methoxy-2-methyl-4(1H)-pyridone (27.8g, 0.2 mol) was added to phosphorus oxychloride (200 mL) and the resulting mixture was heated under nitrogen at 90 oC for 18 h. The homogeneousmixture was cooled to 20 oC and concentrated under reduced pressure.The residue was dissolved in ice-water. Adjustment of the solution to pH 12with 40% sodium hydroxideresulted in a turbid suspension which was extracted with dichloromethane (3 x100 mL). The combined organic extracts were combined, washed with water. After drying the extract with MgSO4,the DCM was removed by rotary evaporation to give the title product (30.2 g,96%). 1H NMR (CDCl3) d 8.14(d, 1H, J = 5.32 Hz), 7.17 (d, 1H, J = 5.10 Hz), 3.85 (s, 3H), 2.54 (s, 3H). m/z (ESI) 157.91 (M+ +1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,76015-11-7, its application will become more common.

Reference:
Article; Maharvi, Ghulam M.; Bharucha, Adil E.; Fauq, Abdul H.; Bioorganic and Medicinal Chemistry Letters; vol. 23; 9; (2013); p. 2808 – 2811;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 717843-56-6, 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 717843-56-6 as follows.

To 3-bromo-2-methoxy-5-methylpyridine [CAS 717843-56-6] (1.0 g, 4.95 mmol) in 20 mL of dry tetrahydrofuran was added Q-Phos (1,2,3,4,5-pentaphenyl-1?-(di-tert-butylphosphino)ferrocene) (0.077 g, 0.109 mmol) and bis(dibenzylideneacetone)palladium (0.091 g, 0.099 mmol). A solution of freshly-prepared (1-(methoxycarbonyl)cyclopropyl)zinc(II) bromide (2.419 g, 9.90 mmol) in tetrahydrofuran (0.45 mmol/mL, 17 mL) was added via a stainless steel cannula under nitrogen pressure. The mixture was stirred at ambient temperature for 40 minutes. Dichloromethane and saturated aqueous NH4Cl were added. The organic layer was washed with brine and concentrated. The residue was purified via chromatography on a 40 g silica gel cartridge, eluting with ethyl acetate in 48 heptane at 0-50% gradient to yield 136 methyl 1-(2-methoxy-5-methylpyridin-3-yl)cyclopropanecarboxylate which was dissolved in 28 methanol (10 mL) and 6M 137 aqueous lithium hydroxide (3 mL) and stirred at 50 C. for 15 hours. The solvent was removed, and 25 water (10 mL) was added. The aqueous layer was extracted with ethyl acetate (10 mL×2). The aqueous layer was adjusted pH 1-2 and extracted with dichloromethane (30 mL×3), and the extracts washed with brine, dried over MgSO4 and concentrated to provide the 138 title compound which used in next step without further purification. MS (APCI+) m/z 208 (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,717843-56-6, its application will become more common.

Reference:
Patent; AbbVie S.a.r.l.; Galapagos NV; Altenbach, Robert J.; Bogdan, Andrew; Couty, Sylvain; Desroy, Nicolas; Gfesser, Gregory A.; Housseman, Christopher Gaetan; Kym, Philip R.; Liu, Bo; Mai, Thi Thu Trang; Malagu, Karine Fabienne; Merayo Merayo, Nuria; Picolet, Olivier Laurent; Pizzonero, Mathieu Rafael; Searle, Xenia B.; Van der Plas, Steven Emiel; Wang, Xueqing; Yeung, Ming C.; (189 pag.)US2019/77784; (2019); 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.6945-67-1, name is 2-Bromo-4-nitropyridine, molecular formula is C5H3BrN2O2, molecular weight is 202.99, as common compound, the synthetic route is as follows.Product Details of 6945-67-1

The 2-[1-hydroxy-1-[4-(naphth-2-ylmethoxy)pyrid-2-yl]propyl]thiazole used as a starting material was obtained as follows: 2-Naphthylmethanol was reacted with 2-bromo-4-nitropyridine (Chem. Abstracts, 1951, 45, 9536) using the conditions described in the first paragraph of the portion of Example 4 which is concerned with the preparation of starting materials except that the reaction mixture was stirred at ambient temperature for 2 hours. There was thus obtained 2-bromo-4-(naphth-2-ylmethoxy)pyridine in 80% yield, m.p. 99-100 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6945-67-1, 2-Bromo-4-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; ICI Pharma; Imperial Chemical Industries PLC; US5089513; (1992); A;,
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. 1221171-70-5, name is 2-Chloro-6-(trifluoromethoxy)pyridine. A new synthetic method of this compound is introduced below., SDS of cas: 1221171-70-5

c) 6-chloro-2-(trifluoromethoxy)-3-(trimethylsilyl)pyridine (1-6); A LDA solution was prepared from n-BuLi 2.5M in hexane (22 mL; 56.80 mmol; 1.1 eq) and diisopropylamine (8 mL; 56.80 mmol; 1.1 eq) in THF (40 mL) at 0C. To the LDA solution at -78 C, a solution of 2-chloro-6-(trifluoromethoxy)pyridine (10.2 g; 51.64 mmol; 1 eq) in THF (40 mL) was added dropwise over 30 minutes. The solution was stirred at -78 C for 2 hours, after what TMSCI (7.20 mL; 56.80 mmol; 1.1 eq) was added dropwise. The reaction mixture was allowed to warm up to room temperature and stirred 1 hour. Water (120 mL) was then added. The aqueous layer was extracted with diethylether (3 x 120 mL), and the combined organic layers were dried over sodium sulphate, filtered and concentrated under reduced pressure. The crude was purified on silica gel using petroleum ether (100 %) as an eluent to afford 6-chloro-2- (trifluoromethoxy)-3-(trimethylsilyl)pyridine in 94 % yield as a colorless oil.1H- MR (CDC13): delta (ppm) 0.33 (s, 9H); 7.21 (d, 1H); 7.77 (d, 1H).

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, 1221171-70-5, 2-Chloro-6-(trifluoromethoxy)pyridine.

Reference:
Patent; VIVALIS; CIAPETTI, Paola; TROUCHE, Nathalie; VENKATA PITHANI, Subhash; GUEDAT, Philippe; BERECIBAR, Amaya; WO2012/93174; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1026796-81-5, 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.1026796-81-5, name is N-(4-Bromopyridin-2-yl)acetamide, molecular formula is C7H7BrN2O, molecular weight is 215.05, as common compound, the synthetic route is as follows.

Step 2: N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]acetamide To a mixture of N-(4-bromopyridin-2-yl)acetamide (17.2 g, 80 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi-1,3,2-dioxaborolane (26.4 g, 104 mmol), Pd(dppf)Cl2 (11.7 g, 16 mmol) and KOAc (23.6 g, 240 mmol) under an atmosphere of nitrogen was added anhydrous DMF (1500 mL). The mixture was allowed to stir at 80 C. for 3.5 h. The solvent was removed and the residue was diluted with EtOAc (1000 mL). Activated carbon (100 g) was added. The slurry was heated at reflux for 5 min and then filtered. The organic solution was concentrated and the residue was recrystallized from EtOAc to give N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]acetamide (6.1 g, 29%) as a white solid. 1H NMR (400 MHz, DMSO-d6): delta 1.29 (s, 12H), 2.09 (s, 3H), 7.24 (dd, J=6.0, 1.2 Hz, 1H), 8.30-8.33 (m, 2H), 10.47 (br s, 1H).

Statistics shows that 1026796-81-5 is playing an increasingly important role. we look forward to future research findings about N-(4-Bromopyridin-2-yl)acetamide.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; Bharathan, Indu T.; Blackburn, Chris; Ciavarri, Jeffrey P.; Chouitar, Jouhara; Cullis, Courtney A.; D’Amore, Natalie; Fleming, Paul E.; Gigstad, Kenneth M.; Gipson, Krista E.; Girard, Mario; Hu, Yongbo; Lee, Janice; Li, Gang; Rezaei, Mansoureh; Sintchak, Michael D.; Soucy, Francois; Stroud, Stephen G.; Vos, Tricia J.; Wong, Tzu-Tshin; Xu, He; Xu, Tianlin; Ye, Yingchun; US2015/225422; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 89510-90-7, 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. 89510-90-7, name is 2-Chloro-5-fluoro-4-pyridinamine. A new synthetic method of this compound is introduced below.

4-Amino-2-chloro-5-fluoropyridine (0.77 g, 4.7 mmol) was carefully added to 7.5 niL of concentrated sulfuric acid at 0-5 C (ice-bath) with stirring to give a solution. Potassium nitrate (1.1 g, 10 mmol) was gradually added to the solution during a period of 10 min while the internal temperature was maintained below 5 C. The reaction mixture was further stirred at 0-5 C for 1 hr and at room temperature for 10 min when TLC showed that all starting material had disappeared and a new product was formed. The mixture was carefully poured onto 30 g of crushed ice. The resulting solution was extracted with methylene chloride (2 x 20 mL). Combined organics were dried, filtered, and concentrated to give the crude product (0.56 g, yield: 61 %), which was directly carried to the next step without purification. LCMS(ESI) m/z: 192.6 [M+H+].Step 5 : 2-Chloro-5-fluoro-4-nitroaminopyridine (560 mg, 2.9 mmol) was carefully added to4.5 mL of concentrated sulfuric acid. The mixture was stirred at room temperature for 12 hrs when TLC showed that the starting material had disappeared and a new product had formed. The mixture was then poured onto 11 g of crushed ice with stirring. The resulting solution was mixed with 20 mL of methylene chloride and neutralized by dropwise addition of 28% ammonium hydroxide with stirring while the internal temperature was maintained below 5 C in a salted ice bath. The organic layer was separated and the aqueous layer was extracted with methylene chloride (2 x 20 mL). The combined organic extracts were dried over MgS04, filtered, evaporated in vacuo to give the crude product (450 mg, yield: 80%), which was carried to the next step without purification. LCMS(ESI) m/z: 192.6 [M+H+].

At the same time, in my other blogs, there are other synthetic methods of this type of compound,89510-90-7, 2-Chloro-5-fluoro-4-pyridinamine, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; LAI, Yingjie; LIANG, Jun; MAGNUSON, Steven R.; TSUI, Vickie H.; ZHANG, Birong; ROBARGE, Kirk; WO2011/113802; (2011); A2;,
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. 89488-30-2, name is 5-Bromo-3-methylpyridin-2(1H)-one. A new synthetic method of this compound is introduced below., Recommanded Product: 5-Bromo-3-methylpyridin-2(1H)-one

Example 509 5-{1-[2-(Difluoromethoxy)benzyl]-2-methyl-1H-benzimidazol-6-yl}-3-methylpyridin-2(1H)-one To Intermediate 57 (140 mg, 0.34 mmol) were added 5-bromo-3-methylpyridin-2-ol (76 mg, 0.41 mmol), Pd(PPh3)4 (20 mg, 0.016 mmol), 2M aqueous Na2CO3 solution (2 mL) and 1,4-dioxane (10 mL). The reaction mixture was stirred at 105 C. for 4 h. Further Pd(PPh3)4 (20 mg, 0.016 mmol) and Na2CO3 solution (1 mL) were added and the reaction mixture was stirred at 105 C. overnight. The reaction mixture was cooled to ambient temperature, diluted with water (1 mL) and extracted with ethyl acetate (2*20 mL). The combined organic layers were concentrated in vacuo and the crude residue was purified by silica flash column chromatography (0-10% MeOH/DCM) and then by preparative HPLC to yield, after freeze-drying, the title compound (3 mg, 2%) as a white solid. deltaH (d6-DMSO) 11.59-11.25 (1H, br s), 7.72 (1H, d, J 1.4 Hz), 7.63-7.49 (3H, m), 7.40-7.33 (3H, m), 7.26 (1H, d, J 7.6 Hz), 7.16-7.11 (1H, m), 6.68-6.65 (1H, m), 5.52 (2H, s), 2.45 (3H, s), 2.00 (3H, s). LCMS (pH 3) 396.8, MH+, RT 1.33 minutes, 100% UV. LCMS (pH 10) 396.8, MH+, RT 1.66 minutes, 100% UV.

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, 89488-30-2, 5-Bromo-3-methylpyridin-2(1H)-one.

Reference:
Patent; Brookings, Daniel Christopher; Calmiano, Mark Daniel; Gallimore, Ellen Olivia; Horsley, Helen Tracey; Hutchings, Martin Clive; Johnson, James Andrew; Kroeplien, Boris; Lecomte, Fabien Claude; Lowe, Martin Alexander; Norman, Timothy John; Porter, John Robert; Quincey, Joanna Rachel; Reuberson, James Thomas; Selby, Matthew Duncan; Shaw, Michael Alan; Zhu, Zhaoning; Foley, Anne Marie; US2015/152065; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 109613-97-0, 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 109613-97-0 as follows.

To an ice-cold solution of 2-bromo-4-methoxypyridin-3-amine (Intermediate 38), (2.74 g) in pyridine (102 mL) was added ethyl chloroformate (1.91 mL) dropwise and then stirred at rt for 45 min. The reaction mixture was cooled in an ice-bath and more ethyl chloroformate (9 mL) added and the mixture left to stir overnight at rt. The reaction mixture was diluted with EtOAc and washed with sat. aq. NaHCO3. The aqueous layer was extracted with EtOAc and the combined organic layers washed with brine, dried over MgSO4, filtered and evaporated under vacuum to give a solid. Product was observed in the aqueous layer by LC-MS, so this was re-extracted with EtOAc (3*) and evaporated under vacuum to give a solid which was combined with the previous solid, dissolved in DCM and purified by column chromatography (normal phase, 50 g, Biotage SNAP cartridge KP-Sil, 50 mL/min, gradient 10-70% EtOAc in n-hexane) to give the desired product (2.35 g). LCMS: m/z 275.43 [M+H]+. 1H NMR (400 MHz, CDCl3) ppm 1.32 (t, J=7.1 Hz, 3H) 3.93 (s, 3H) 4.24 (q, J=7.1 Hz, 2H) 6.06 (br. s., 1H) 6.86 (d, J=5.6 Hz, 1H) 8.19 (d, J=5.6 Hz, 1H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,109613-97-0, its application will become more common.

Reference:
Patent; Payne, Andrew; Castro Pineiro, Jose Luis; Birch, Louise Michelle; Khan, Afzal; Braunton, Alan James; Kitulagoda, James Edward; Soejima, Motohiro; US2015/94328; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 766557-60-2, 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. 766557-60-2, name is 2-Ethoxy-3-iodopyridine, molecular formula is C7H8INO, 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.

An excess of saturated ammonium chloride solution was added, followed by ethyl acetate, the mixture being stirred for 5 minutes. The aqueous phase was separated off and extracted with ethyl acetate (2*). The combined organic phases were washed with water (2*), and the solvent was removed in vacuo. During this, unreacted 5-iodoisatin precipitated first from the still dilute solution and was separated off. After further concentration, finally the title compound also crystallized. The suspension was stored in a refrigerator at 5 C. for 2 hours. The precipitated, pale yellow solid was then filtered off and washed with a little ethyl acetate. After drying at 40 C., (±)-3-(2-ethoxypyridin-3-yl)-3-hydroxy-5-iodo-1,3-dihydro-2H-indol-2-one (17.1 g, 43.16 mmol, 57%) was isolated. ESI-MS [M+H+]=397.05 calculated for C15H13IN2O3=396.19

According to the analysis of related databases, 766557-60-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Abott GmbH & Co KG; US2011/65720; (2011); 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. 23612-36-4, name is 3-Bromo-1H-pyrrolo[3,2-c]pyridine. A new synthetic method of this compound is introduced below., Computed Properties of C7H5BrN2

To a mixture of Intermediate 1 (1.80 g, 9.14 mmol) in DCM (60 mL) was added di-tert- butyl dicarbonate (2.18 g, 10.0 mmol) followed by 4-dimethylaminopyridine (122 mg, 1.00 mmol). After 80 min the solution was diluted with DCM (20 mL) and washed with 0.1 M HC1 (25, 10 mL) and brine. The organic layer was dried (Na2S04), filtered and evaporated to yield the title compound as a light yellow solid (2.47 g, 90%). MS (ESI+) m/z = 299 (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, 23612-36-4, 3-Bromo-1H-pyrrolo[3,2-c]pyridine.

Reference:
Patent; Proximagen Limited; EVANS, David; CARLEY, Allison; STEWART, Alison; HIGGINBOTTOM, Michael; SAVORY, Edward; SIMPSON, Iain; NILSSON, Marianne; HARALDSSON, Martin; NORDLING, Erik; KOOLMEISTER, Tobias; WO2011/113798; (2011); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem