Category: pyridine-derivatives

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. 53710-18-2, name is 3,5-Diiodopyridine. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C5H3I2N

To a mixture of 4-(3-butenyloxy)-2,6-diethynylpyridine (4, 0.10 g, 0.51 mmol), 3,5-diiodopyridine (6, 0.63 g, 2.0 mmol), Pd(PPh3)4 (24 mg,21 mol), i-Pr2NH (2.5 mL), and THF (20 mL) was added CuI (3.9 mg, 20 mol), and the mixture wasstirred for 5 h at room temperature. The resulting mixture was treated with a Florisil bed and given a rinsewith AcOEt. The filtrate was concentrated by a rotary evaporator and the resulting residue was subjectedto silica gel column chromatography (eluent: CHCl3 to CHCl3/MeOH = 50:1) to give 7 as a colorless solid(0.16 g, 52%). Mp 196-198 C; IR (KBr) 3047, 2925, 2222, 1582, 1550 cm-1; 1H NMR (CDCl3) 2.57-2.64 (m, 2 H), 4.13 (t, J = 6.6 Hz, 2 H), 5.15-5.23 (m, 2 H), 5.82-5.95 (m, 1 H), 7.07 (s, 2 H), 8.21 (s,2 H), 8.73 (s, 2 H), 8.81 (s, 2 H); 13C NMR (CDCl3) 33.2, 67.8, 84.0, 92.1, 92.4, 113.9, 117.9, 120.8, 133.1,143.8, 146.6, 150.7, 155.2, 165.1; HRMS (ESI-TOF) calcd for C23H16I2N3O (M + H+): 603.9383; m/zfound: 603.9362.

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, 53710-18-2, 3,5-Diiodopyridine.

Reference:
Article; Abe, Hajime; Suzuki, Daiki; Shimizu, Ayako; Inouye, Masahiko; Heterocycles; vol. 88; 1; (2014); p. 547 – 557;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 86847-84-9 , The common heterocyclic compound, 86847-84-9, name is N-(6-Chloropyridin-2-yl)pivalamide, molecular formula is C10H13ClN2O, 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 2-chloro-6pivaloylaminopyridine (10.5 g, 49.528 mmol) in THF (150 mL) is prepared under N2 and cooled to -80 0C. t-BuLi IM in pentane (108.962 mmol, 2.2 equiv.) is added carefully via an addition funnel under rigorously anhydrous conditions, over 1 hour. Once the addition is complete, the mixture is kept at -8O0C for 3 hours, at which point a solution of iodine (15.1 g, 59.431 mmol, 1.2 equiv.) in 50 mL THF under N2, is added slowly in one portion. After the addition, the cooling bath is removed and the reaction mixture allowed to warm up to room temperature under stirring for 2 hours. Finally the reaction mixture is quenched by slowly adding 50 mL of IM HCl. The mixture is then concentrated under vacuum to remove part of the THF, and the residue is partitioned between EtOAc and water. A 10% sodium thiosulfate solution is added until no further decolourisation occurred and that 2 clear phases are visible. The aqueous layer is extracted with EtOAc, the organic layers are gathered, washed with brine, dried over Na2Stheta4, and solvent is removed to afford an oil titrating 65 % of the desired material. This crude is refluxed in 100 mL of IM HCl and is refluxed for 5 hours at which point the depivaloylated product is completely formed. The pH is adjusted to 12 by slow addition OfNaHCO3 and extracted with DCM. The organic layer is concentrated and columned using 7/3 DCM/Cyclohexane as the eluent (Rf 9/21) to afford the title compound as an oil which solidified on standing

The synthetic route of 86847-84-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GALAPAGOS N.V.; WO2008/65199; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 83766-88-5, 2-(tert-Butoxy)pyridine, 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, 83766-88-5, blongs to pyridine-derivatives compound. category: pyridine-derivatives

Carboxylic acid (0.2 g, 1.64 mmol), tert-butoxypyridine (0.33 g, 2.21 mmol) and boron trifluoride diethyl etherate (0.31 g, 2.21 mmol) in dry PhCH3 (2 mL) were added to a 20-ml vial. The reaction mixture was then allowed to stir at room temperature for 30 min before quenching with anhydrous NaHCO3. The reaction mixture was diluted with ethyl acetate (30 mL), then washed with water (20 mL), followed by brine (20 mL). The organic layer was dried over anhydrous sodium sulfate and carefully concentrated under reduced pressure. The resulting residue was then purified by flash column chromatography on silica gel with 0:4 to 1:4 dichloromethane/hexane as eluent to yield the desired product 5a as a colorless oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,83766-88-5, its application will become more common.

Reference:
Article; La, Minh Thanh; Kim, Hee-Kwon; Tetrahedron; vol. 74; 27; (2018); p. 3748 – 3754;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 112110-07-3, 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. 112110-07-3, name is 5-(Trifluoromethyl)pyridin-3-amine. A new synthetic method of this compound is introduced below.

To a solution of 1-(1-oxo-1,2-dihydroisoquinolin-5-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid (345.9 mg, 0.888 mmol) and 5-(trifluoromethyl)pyridin-3-amine (120 mg, 0.74 mmol) in pyridine (3 mL) was added POCl3 (227 mg, 1.48 mmol) dropwise. The mixture was stirred at 25 C. for 4 h and at 40 C. for 3 h. Sat. NaHCO3 was added to adjust the pH to 7-8 and the mixture was extracted with ethyl acetate (30 mL*2). The combined organic layers were dried over MgSO4, filtered and the filtrates were concentrated under reduced pressure to afford crude product as a yellow oil. The crude product was then purified by preparative HPLC (37% to 57% (v/v) CH3CN and H2O with 0.05% HCl) to afford 1-(1-oxo-1,2-dihydroisoquinolin-5-yl)-5-(trifluoromethyl)-N-(5-(trifluoromethyl)pyridin-3-yl)-1H-pyrazole-4-carboxamide (130 mg, 37%). 1H NMR (400 MHz, DMSO-d6) delta ppm 5.67 (d, J=7.28 Hz, 1H), 7.26-7.31 (m, 1H), 7.68 (t, J=7.94 Hz, 1H), 7.94 (d, J=7.50 Hz, 1H), 8.44 (d, J=7.94 Hz, 1H), 8.53 (s, 1H), 8.60 (s, 1H), 8.75 (s, 1H), 9.12 (s, 1H), 11.18 (s, 1H), 11.64 (br d, J=4.63 Hz, 1H). LC-MS: (ES, m/z): [M+1]+ 467.9

At the same time, in my other blogs, there are other synthetic methods of this type of compound,112110-07-3, 5-(Trifluoromethyl)pyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; Janssen Biotech, Inc.; Lu, Tianbao; Allison, Brett Douglas; Barbay, Joseph Kent; Connolly, Peter J.; Cummings, Maxwell David; Diels, Gaston; Edwards, James Patrick; Kreutter, Kevin D.; Philippar, Ulrike; Shen, Fang; Thuring, Johannes Wilhelmus John Fitzgerald; Wu, Tongfei; (412 pag.)US2018/170909; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 72583-83-6, 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.72583-83-6, name is 1-Methyl-1H-pyrazolo[3,4-b]pyridin-3-ylamine, molecular formula is C7H8N4, molecular weight is 148.17, as common compound, the synthetic route is as follows.

In a vial, to a mixture of intermediate 5 (0.02 g, 0.07 mmol), 7-methoxy-4,5- dihydronaphtho[l,2-d]thiazol-2-amine (0.02 g, 0.07 mmol) was added BOP (0.030 g, 0.069 mmol), DMF (0.3 mL), and DIEA (0.060 ml, 0.35 mmol). After 72 h, the reaction mixture was filtered and subjected to reverse phase HPLC purification to afford Example 1 (4.4 mg, 9.9 %). NMR (500MHz, OMSO-d6) delta 8.34 – 8.04 (m, 2H), 7.85 – 7.81 (m, 1H), 7.80 – 7.73 (m, 1H), 7.58 (d, J=8.2 Hz, 1H), 7.42 – 7.29 (m, 2H), 7.27 – 7.12 (m, 2H), 6.91 – 6.79 (m, 2H), 3.83 (s, 2H), 3.33 (br s, 1H), 3.02 – 2.93 (m, 2H), 2.92 – 2.84 (m, 2H), 3.77 (s, 3H). LCMS m/z = 505.0 (M+H)+; HPLC purity > 96% with retention time 1.81 min. [method A]

The chemical industry reduces the impact on the environment during synthesis 72583-83-6, I believe this compound will play a more active role in future production and life.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ORWAT, Michael J.; PINTO, Donald J. P.; (183 pag.)WO2019/14300; (2019); A1;,
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. 107867-51-6, name is 5-(Trifluoromethyl)pyridine-2,3-diamine, molecular formula is C6H6F3N3, 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. HPLC of Formula: C6H6F3N3

[(C)] [6-TRIFLUOROMETHYL-1,] 3-diliydro-imidazo [4,5-b] pyridin-2-one, trifluoroacetic acid salt. A mixture of 5-trifluoromethyl-pyridine-2, 3-diamine from step (b) above and N, [N-CARBONYLDIIMIDAZOLE] (938 mg, 579 mmol, Aldrich) in THF (10 mL) was stirred at room temperature for 16 h. The reaction mixture was diluted with [HA0] (20 mL) and extracted with EtOAc (2 x 30 mL). The combined organic extracts were concentrated in vacuo and the residue was purified by preparative HPLC (gradient 0. [1 %] trifluoroacetic acid in acetonitrile) to give the title compound. MS (ESI positive ion) m/z: 204 (M+1).

With the rapid development of chemical substances, we look forward to future research findings about 107867-51-6.

Reference:
Patent; AMGEN INC.; WO2004/35549; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 380380-64-3, 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. 380380-64-3, name is 5-Bromo-2-(2-methyl-2H-tetrazol-5-yl)pyridine, molecular formula is C7H6BrN5, 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.

Under the protection of nitrogen, add 17.7g of 2-methyl-5- (5-bromopyridin-2-yl) tetrazole, 27.7g of borate intermediate, 0.663g of tricyclohexylphosphine and 0.23L of dioxane Stir to dissolve; add a solution of potassium carbonate 175g in water 70mL at one time; add 0.88g of tris (dibenzylideneacetone) dipalladium, vacuum-nitrogen replacement three times, then heat the reaction to 70C, and keep the reaction for 1 hour, filter the reaction Liquid, rinse, add 15% saline solution to the mother liquor (the mass concentration refers to the mass of sodium chloride as a percentage of the total mass of saline solution) 100mL, separate layers, separate organic phase, and concentrate in vacuum (temperature 45 65 , pressure -0.08MPa -0.1MPa) to dry, the crude product is stirred in ethyl acetate 120mL) for 12 hours to 16 hours and filtered, and the wet product is dried in a vacuum (pressure -0.01MPa -0.1MPa) oven Dry at 45 C to 55 C for 8 hours to 12 hours to obtain 26.0 g of off-white solid as terdazolamide phosphate II, with a total yield of 55.1% (based on benzyl 3-fluoro-4-bromophenylcarbamate) ). HPLC purity 96.23%.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 380380-64-3, 5-Bromo-2-(2-methyl-2H-tetrazol-5-yl)pyridine.

Reference:
Patent; Shanghai Bozhi Yan Xin Pharmaceutical Co., Ltd.; Chen Jian; Liu Zhenfeng; Ying Shuhuan; (16 pag.)CN110804038; (2020); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 116855-08-4, 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.116855-08-4, name is 1H-Pyrazolo[3,4-b]pyridine-3-carboxylic acid, molecular formula is C7H5N3O2, molecular weight is 163.13, as common compound, the synthetic route is as follows.

To a solution of 1H-pyrazole[3,4-b]pyridine-3-carboxylic acid (XV) (0.39 g, 2.4 mmol) in dry MeOH (10 mL) was added concentrated H2SO4 (4 drops) and refluxed for 6 h under nitrogen. The solution was cooled and the solvent was evaporated under vacuum. The residue was partitioned between DCM and saturated aqueous NaHCO3 solution. The organic layer was separated, dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was purified on a flash silica gel column (100% DCM?3:97 MeOH:DCM) to produce methyl 1H-pyrazolo[3,4-b]pyridine-3-carboxylate (XVI) as a white solid (382 mg, 2.16 mmol, 90% yield). 1H NMR (CDCl3) delta ppm 4.08 (s, 3H), 7.38 (m, 1H), 8.63 (dd, J=8.10 Hz, J=1.51 Hz, 1H), 8.72 (dd, J=4.62 Hz, J=1.41 Hz, 1H); ESIMS found for C8H7N3O2 m/z 178.2 (M+H)

Statistics shows that 116855-08-4 is playing an increasingly important role. we look forward to future research findings about 1H-Pyrazolo[3,4-b]pyridine-3-carboxylic acid.

Reference:
Patent; Samumed, LLC; Hood, John; Kumar KC, Sunil; Wallace, David Mark; US2013/296302; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 877133-54-5, 4-Bromo-2,6-diethylpyridine, 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, Recommanded Product: 4-Bromo-2,6-diethylpyridine, blongs to pyridine-derivatives compound. Recommanded Product: 4-Bromo-2,6-diethylpyridine

Zinc cyanide (546 mg, 4.67 mmol) was added to a degassed solution of 4-bromo-2,6- diethylpyridine (500 mg, 10.8 mmol) and tetrakis(triphenylphoshpine) palladium (137 mg, 0.17 mmol) in dry DMF (5 ml_). The resulting reaction mixture was heated at 100C for 16 h. The mixture was cooled to room temperature, diluted with ethyl acetate (15 ml_) and filtered through Celite. The filter cake was washed with ethyl acetate (2 x 10 ml_). The combined organic filtrate was washed with water (10 ml_) and saturated aqueous NaCI, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by flash chromatography, eluting with 40% to 60% ethyl acetate in petroleum ether, to afford 2,6-diethylisonicotinonitrile (270 mg, 73%). 1H NMR: 6H (300 MHz, DMSO-c/6) 7.56 (2H, s), 2.77 (4H, q, J 7.5), 1.23 (6H, t, 7.5).

The synthetic route of 877133-54-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MIRONID LIMITED; ADAM, Julia Mary; ADAMS, David Roger; KULKARNI, Santosh Shripad; NANDURDIKAR, Rahul Shripad; (131 pag.)WO2019/193342; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 23056-47-5, 2-Bromo-4-methyl-5-nitropyridine, 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 23056-47-5, blongs to pyridine-derivatives compound. Product Details of 23056-47-5

2-Bromo-4-methyl-5-nitropyridine (2.5g, 11.58mmol) was dissolved in concentrated sulfuric acid (25mL), cooled to ice bath 0C, chromium trioxide (3.88g, 38.8mmol) was added. It was slowly warmed to room temperature and stirred overnight. The reaction mixture was poured into ice water (75 mL), stirred for 10 minutes and suction filtered to give a white solid (2.5g, yield: 87.8%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,23056-47-5, 2-Bromo-4-methyl-5-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; Nanjing Yaojie Good Health Biological Technology Co., Ltd.; Wu Yongqian; Li Lin; Yang Xiaoju; (118 pag.)CN109575016; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem