Pyridine-derivatives

Electric Literature of 72587-15-6 , The common heterocyclic compound, 72587-15-6, name is 2-Chloro-3-nitro-5-(trifluoromethyl)pyridine, molecular formula is C6H2ClF3N2O2, 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.

Step A. Alternative preparation of N-cyclobutyl-3-nitro-5-(trifluoromethyl)pyridin-2-amine To a mixture of 2-chloro-3-nitro-5-(trifluoromethyl)pyridine (1.00 g, 4.41 mmol) and NaHCO3 (1.12 g, 13.2 mmol) in EtOH (10 mL) was added cyclobutylamine (0.94 g, 13.2 mmol) drop-wise over 10 minutes. The mixture was stirred for 30 min, absorbed onto silica and purified on a 40 g ISCO gold silica gel column, eluting with a hexanes (100%) to hexanes (95%)/EtOAc (5%) gradient, to provide the desired compound (1.05 g, 91%) as a bright yellow solid.

The synthetic route of 72587-15-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KNOPP BIOSCIENCES LLC; Resnick, Lynn; Topalov, George T.; Boyd, Steven A.; Belardi, Justin K.; Flentge, Charles A.; Hale, James S.; Harried, Scott S.; Mareska, David A.; Zhang, Kai; Heap, Charles R.; Hadden, Mark; Cui, Wenge; Decornez, Helene; Liu, Shuang; (146 pag.)US2016/31875; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 55758-32-2, 6-Fluoropyridin-3-ol, 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, category: pyridine-derivatives, blongs to pyridine-derivatives compound. category: pyridine-derivatives

A mixture of 6-fluoro-pyridin-3-ol (280 mg), toluene-4-sulfonic acid 3-hydroxy-3- methyl-butyl ester (721 mg), and cesium carbonate (807 mg) in N,N10 dimethylformamide (10 mL) is heated to 50 C for 2 h. The reaction mixture dilutedwith water and extracted with ethyl acetate. The combined extracts are dried overMgSO4 and concentrated in vacuo. The residue is chromatographed on silica gel(cyclohexane/ethyl acetate 70:30) to give the title compound. LC (method 5): tR =0.81 mm; Mass spectrum (ESl): mlz = 200 [M+H].

The synthetic route of 55758-32-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ECKHARDT, Matthias; FRATTINI, Sara; LANGKOPF, Elke; WAGNER, Holger; WO2014/86712; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 17282-40-5 ,Some common heterocyclic compound, 17282-40-5, molecular formula is C9H12BrNO2, 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.

General procedure: Chromenone 1a (0.5 mmol), pyridinium salts 2a (0.55 mmol), DBU (1.0 mmol) and 1,4-dioxane (3.0 mL) were dissolved in 10 mL round-bottomed flask and stirring at 80 C for 12 h. The reaction was monitored by TLC. After completion of reaction, the reaction mixture was cooled down to room temperature and concentrated in vacuum to give the crude product, which was further purified by silica gel chromatography (ethyl acetate: petroleum =1:5) to afford the desired product. 1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,17282-40-5, its application will become more common.

Reference:
Article; Dong, Kai-Kai; Huang, Qiang; Tetrahedron Letters; vol. 60; 29; (2019); p. 1871 – 1874;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 123148-66-3, 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 123148-66-3, name is (2-Methoxypyridin-4-yl)methanol. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of the above compound (V2) (440 mg, 3.16 mmol) in CH2CI2 (12.6 ml) at room temperature was added drop-wise thionyl chloride (0.69 ml, 9.49 mmol). The resulting mixture was stirred at room temperature for 2 h. The solvent was removed. The residue was washed with sat. NaHC03 and extracted with CH2CI2. The combined organic layers were washed with brine, dried over anhydrous MgS04, filtered and concentrated to give 4-(chloromethyl)-2- methoxypyridine (V3) (400 mg, 80%) as a light yellow liquid. ES-MS [M+l]+: 158.1.

According to the analysis of related databases, 123148-66-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott, D.; SCHLEGEL, Kelly-Ann; YANG, Zhi-Qiang; WO2011/84368; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 69045-79-0, 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. 69045-79-0, name is 2-Chloro-5-iodopyridine. A new synthetic method of this compound is introduced below.

Zinc dust (127mg, 1.94mmol, 1.1eq) was dried for 18h at 100C in vacuo, transferred to a round bottomed flask and heated with a hot air gun under vacuum. The flask was allowed to cool to room temperature and DMF (2ml) and 1,2-dibromoethane (12mul, 0.141mmol, 0.08eq) added. The mixture was heated to 70C for 10 mins, allowed to cool to r. t., and TMSCI (18mul, 0.141mmol, 0.08eq) added dropwise. This mixture was stirred at r. t. for 30min before dropwise addition of 3-iodoazetidine-1-carboxylic acid tert-butyl ester (Ref SynLett, 1998,4, 379)(500mg, 1.766mmol, 1.Oeq) as a solution in DMF (2ml). The mixture was stirred at 40C for 1 h. 2-chloro-5-iodopyridine was dissolved in DMF (2ml) and added, followed by Pd2dba3 (32mg, 0.035mmol, 0.02eq) and tri-2-furylphosphine (17mg, 0.071mmol, 0.04eq) and the mixture heated to 70C for 4h. The mixture was allowed to cool, diluted with Et20(40ml) and NH4CI (40ml, sat’d aq), layers separated, the aqueous layer was re-extracted with Et20(20ml), organics combined, washed with brine (2x30ml), dried (MgS04), filtered and evaporated to give a yellow solid. This solid was flash chromatographed on silica gel with a gradient elution from 100% CH2CI2 to 99: 1 CH2CI2:MeOH to give 235mg of impure product. This material was further purified by fish chromatography on silica get with a gradient elution from 100% toluene to 95:5 toluene:EtOAc to give the title compound as a yellow solid (193mg, 41%) Tlc Rf = 0.13 (10%EtoAc/Toluene UV visualisation) MS (APCI+) 269 (MH+) ¹H NMR: No.H (400 MHz, CDCI3) 8.3 (1 H, s), 7.7 (1 H, m), 7.35 (1 H, d), 4.35 (2H, t), 3.9 (2H, t), 3.65-3.8 (1 H, m), 1.45 (9H, s)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,69045-79-0, 2-Chloro-5-iodopyridine, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER LIMITED; PFIZER INC.; WO2005/115985; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 6969-71-7 ,Some common heterocyclic compound, 6969-71-7, molecular formula is C6H5N3O, 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 the commercially available [112,4]triazolo[4,3-a]pyridin-3(2H)-one (27 mg, 0.20 mmol) and 18-crown-6 ether (55 mg, 0.21 mmol) in anhydrous 1 ,4-dioxan (1 ml.) was added a 1 M solution of potassium te/t-butoxide in tetrahydrofuran (210 mul_, 0.21 mmol) . The mixture was stirred at room temperature for 15 minutes and then 1 ml_ of a solution of 3,4-dichloro-N-[5-chloro-2-(chloromethyl)phenyl]benzenesulfonamide (655 mg, 1.7 mmol) in anhydrous 1 ,4-dioxane (17 mL) was added. The mixture was heated at 60 0C for 15 hours and then left to cool to room temperature. The solvent was removed under reduced pressure and the residue dissolved in dimethyl sulphoxide (0.5 mL) and then purified by mass directed autoprep to give 3,4-dichloro-N-{5-chloro-2-[(3- oxo[1 ,2,4]triazolo[4,3-a]pyridin-2(3H)-yl)methyl]phenyl}benzenesulfonamide as a white solid (6.6mg). HPLC Rt = 3.23 minutes; m/z [M+H]+ = 483. 1H NMR (d6-DMSO) delta 7.85 (m, 3H), 7.63 (d, 1 H), 7.28 (d, 1 H), 7.24 (t, 1 H), 7.17 (d, 1 H), 7.09 (d, 1 H), 6.99 (s, 1 H), 6.63 (t, 1 H)1 5.00 (S1 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6969-71-7, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMTED; WO2007/14054; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 164513-39-7, 5-Bromo-2-methoxy-4-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, SDS of cas: 164513-39-7, blongs to pyridine-derivatives compound. SDS of cas: 164513-39-7

Intermediate 31 (50% purity, 165 mg, 0.25 mmol), 5-bromo-2-methoxy-4-methyl-pyridine (75 mg, 0.37 mmol) and 2M aqueous potassium carbonate solution (0.43 mL)were combined in 1 ,4-dioxane (5 mL). Bis[3-(diphenylphosphanyl)cyclopenta-2,4-dien- 1 -yl]iron-dichloropalladium-dichloromethane complex (10 mg, 0.01 mmol) was added, and the mixture was heated at 90C for 18 h. The mixture was partitioned between ethyl acetate (20 mL) and water (15 mL). The organic layer was dried over sodium sulfate andconcentrated under vacuum. The residue was purified by flash chromatography, eluting with 0-100% ethyl acetate in heptanes followed by 0-20% methanol in DCM. The crude product was then further purified by preparative HPLC (Method C) to afford the title compound (23 mg, 23%) as a white solid. OH NMR (500 MHz, CDC13) 7.89 (s, 1H), 7.62(d, J9.2 Hz, 1H), 7.59 (s, 1H), 7.24 (d, J7.3 Hz, 1H), 7.13 (d, J8.1 Hz, 1H), 7.10 (dd, J9.2, 1.3 Hz, 1H), 7.06 (t, J7.5 Hz, 1H), 6.83 (d, J7.4 Hz, 1H), 6.55 (m, 2H), 4.28 (s, 2H),3.93 (s, 3H), 2.52 (s, 3H), 2.11 (s, 3H). Method A HPLC-MS: MH+ m/z 410, RT 3.20 minutes (99%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,164513-39-7, 5-Bromo-2-methoxy-4-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; UCB PHARMA S.A.; BENTLEY, Jonathan Mark; BROOKINGS, Daniel Christopher; BROWN, Julien Alistair; CAIN, Thomas Paul; CHOVATIA, Praful Tulshi; FOLEY, Anne Marie; GALLIMORE, Ellen Olivia; GLEAVE, Laura Jane; HEIFETZ, Alexander; HORSLEY, Helen Tracey; HUTCHINGS, Martin Clive; JACKSON, Victoria Elizabeth; JOHNSON, James Andrew; JOHNSTONE, Craig; KROEPLIEN, Boris; LECOMTE, Fabien Claude; LEIGH, Deborah; LOWE, Martin Alexander; MADDEN, James; PORTER, John Robert; QUINCEY, Joanna Rachel; REED, Laura Claire; REUBERSON, James Thomas; RICHARDSON, Anthony John; RICHARDSON, Sarah Emily; SELBY, Matthew Duncan; SHAW, Michael Alan; ZHU, Zhaoning; WO2014/9295; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 181123-11-5, Adding some certain compound to certain chemical reactions, such as: 181123-11-5, name is 5-Chloro-2-cyano-3-nitropyridine,molecular formula is C6H2ClN3O2, 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 181123-11-5.

Step 2;. Preparation of 3-Amino-5-chloro-pyridine-2-carboxylic acid methyl ester; Heat at 90 C a mixture of 5-chloro-3-nitro-pyridine-2-carbonitrile (1.0 g, 5.90 mmol) and tin (II) chloride (6.79 g, 29.5 mmol) in ethanol (10 mL) for 3 h. Evaporate the solvent under reduced pressure, add a solution of 35% hydrochloric acid (5 mL) and reflux the mixture for 6 h. Concentrate the reaction in vacuo to dryness and dissolve the resulting residue in methanol (20 mL). Add thionyl chloride (0.95 mL, 7.08 mmol) at room temperature and heat the mixture at 90 C for 24 h. Remove the solvent under reduced pressure, add ethyl acetate, and wash with a saturated solution of sodium bicarbonate. Separate the organic layer, dry over sodium sulfate, filter, and concentrate under reduced pressure. Purify the residue using silica gel chromatography, eluting with ethyl acetate to afford the title compound (0.77 g, 70%). H-NMR (CDCl3, 3 00 MHz): 8 3.97 (s, 3 H) ; 5.85 (bs, 2 H) ; 7.06 (d, J = 2.0 Hz, 1H), 7.97 (d, J = 2.0 Hz, 1H).

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. 181123-11-5, 5-Chloro-2-cyano-3-nitropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/97805; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 866546-07-8, 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 866546-07-8, name is 5-Chloro-1H-pyrrolo[2,3-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows.

Example 18: Synthesis of 5-chloro-3-2-chIoro-5-fluoro-4-[2-(2-methoxy-ethoxy)-ethoxy]-benzyl- lH-pyrrolo[2,3-b]pyridine P-2155.[0192] 5-Chloro-3-2-chloro-5-fluoro-4-[2-(2-methoxy-ethoxy)-ethoxy]-benzyl-lH-pyrrolo[2,3- b]pyridine P-2155 was synthesized in 2 steps from 5-Chloro-lH-pyrrolo[2,3-b]pyridine 4 as shown in Scheme 40.Scheme 40 Step 1 – Preparation of2-chloro-5-fluoro-4-[2-(2-methoxy-ethoxy)-ethoxy]-phenyl-(5-chloro-lH- pyrrolo[2,3-b]pyridiotan-3-yl)-methanol (126).[0193] To 5-chloro-l H-pyrrolo[2,3-b]pyndine (4. 74.1 mg, 0 49 mmol) in methanol (30.0 mL), 2- chloro-5-fluoro-4-[2-(2-methoxy-ethoxy)-ethoxy]-benzaldehyde (121, 150.0 mg, 0.54 mmol, prepared as described in Example 14) and potassium hydroxide (574 0 mg, 10.23 mmol) were added under an atmosphere of nitrogen. The reaction was stirred at room temperature overnight The reaction was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered The filtrate was concentrated and purified by silica gel column chromatography eluting with 20% ethyl acetate in hexane to give the desired compound (126, O H g, 52.7%).

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 866546-07-8, 5-Chloro-1H-pyrrolo[2,3-b]pyridine.

Reference:
Patent; PLEXXIKON, INC.; WO2008/80001; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 20173-24-4, 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.20173-24-4, name is 2-(Pyridin-3-yl)ethanamine, molecular formula is C7H10N2, molecular weight is 122.1677, as common compound, the synthetic route is as follows.

To a solution of 2-[(9R)-9-(pyridin-2-yl)-6-oxaspiro[4.5]decan-9-yl]acetaldehyde (50 mg, 0.19 mmole), 5 mL DCM and NA2S04 (134 mg, 0.95 mmole) was added 2-(pyridin-3- yl)ethan-l -amine (31 mg, 0.25 mmole) and the reaction was stirred overnight. NaBH4 (9.5 mg, 0.25 mmole) added, stir 10 minutes, 2 drops MeOH added, stir lh, quenched with water, organics separated off and evaporated. The residue was passed through a Gilson reverse phase HPLC to give {2-[(9R)-9-(pyridin-2-yl)-6-oxaspiro[4.5]decan-9- yl]ethyl}[2-(pyridin-3-yl)ethyl]amine, 65.3 mg (71%). LCMS m/z 367.1 (M + 1) observed

The chemical industry reduces the impact on the environment during synthesis 20173-24-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; TREVENA, INC.; VIOLIN, Jonathan D.; SOERGEL, David G.; (177 pag.)WO2017/106547; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem