Day: September 14, 2021

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.6231-18-1, name is 2,6-Dimethoxypyridine, molecular formula is C7H9NO2, molecular weight is 139.15, as common compound, the synthetic route is as follows.Application In Synthesis of 2,6-Dimethoxypyridine

Comparative Example 1 In a 50 cc short-neck flask, 0.751 g of 2,6-dimethoxypyridine, 18 ml of 35% hydrochloric acid and 18 ml of acetic acid were placed, and then the flask was dipped in an oil bath of 140 C. while conducting stirring reflux for 1 hour. The reaction mixture was analyzed using liquid chromatography, showing a yield of 2,6-dihydroxypyridine of 28.8% and a residual ratio of the starting material (2,6-dimethoxypyridine) of 51.2%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6231-18-1, 2,6-Dimethoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; Kato, Syunsaku; Suzuki, Daisuke; Seo, Yoshiko; US2002/157939; (2002); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 5470-22-4, 4-Chloropicolinic 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, Quality Control of 4-Chloropicolinic acid, blongs to pyridine-derivatives compound. Quality Control of 4-Chloropicolinic acid

General procedure: To a solution of the picolinic acid S7 (25.0 mmol) in DCM (100 mL) at room temperature was added SOCl2 (20 mL) and some drops of dry DMF. The reaction was allowed to stir at 50 C for 3 hours. The solvent was then removed under reduced pressure to afford the corresponding crude acid chloride (S8). Then DCM (40 mL) was added and the solution was cooled to 0C followed by dropwise addition of NEt3 (75.0 mmol, 3.0 eq) and N,O-dimethylhydroxylamine (50.0mmol, 2.0 eq). The reaction mixture was stirred at rt overnight, extracted by DCM, the organic layerwas dried over Na2SO4 and the solvent was evaporated, then purified by flash chromatography to gain the corresponding amides (S9).

The synthetic route of 5470-22-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jin, Liang; Yao, Qi-Jun; Xie, Pei-Pei; Li, Ya; Zhan, Bei-Bei; Han, Ye-Qiang; Hong, Xin; Shi, Bing-Feng; Chem; vol. 6; 2; (2020); p. 497 – 511;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 76006-17-2 , The common heterocyclic compound, 76006-17-2, name is 1H-Pyrazolo[3,4-c]pyridin-3-amine, molecular formula is C6H6N4, 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.

Tert-butyl 4-(3-ethoxy-3-oxopropanoyl)piperidine-l-carboxylate (1.00 g, 3.34 mmol, 1.5 eq), 1H- pyrazolo[3,4-c]pyridin-3-amine (299 mg, 2.27 mmol, 1 eq) and potassium phosphate (945 mg, 4.45 mmol, 2 eq) were suspended in l-methoxy-2-propanol (10 mL) in a 20 mL microwave vial. The vial was capped and the mixture was heated in a microwave to 180C for 15 min. After cooling to RT, the suspension was diluted with water (20 mL) and neutralized (pH 7) by the addition of IN HCl. The precipitate was filterered, washed with water (10 mL) and dried for 16 h at 50C in vacuo to yield the title compound (169 mg, 75% purity, 16% of theory). LC-MS (Method IB): Rt = 0.73 min, MS (ESIPos): m/z = 370 [M+H]+

The synthetic route of 76006-17-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; HASSFELD, Jorma; KINZEL, Tom; KOeBBERLING, Johannes; CANCHO-GRANDE, Yolanda; BEYER, Kristin; ROeHRIG, Susanne; KOeLLNBERGER, Maria; SPERZEL, Michael; BURKHARDT, Nils; SCHLEMMER, Karl-Heinz; STEGMANN, Christian; SCHUHMACHER, Joachim; WERNER, Matthias; ELLERMANN, Manuel; WO2015/67549; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 929022-76-4, 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. 929022-76-4, name is 2-Chloro-4-fluoronicotinic acid, molecular formula is C6H3ClFNO2, 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.

To a solution of Example 75a (2.74 g, 15.6 mmol) in THF (50 mL), tBuOCOCl ( 3.2 g, 23.4 mmol) at 0C was added TEA (3.16 g, 31.2 mmol), the mixture was stirred at r.t. for 0.5 min, and then NaBD4 ( 1.31 g, 31.2 mmol) in EtOH (10 mL) was added at 0C, which was turned to r.t for another 30 min. The reaction was then quenched by adding water (10 mL), then concentrated, the residue was purified by flash column chromatography (eluted with EtOAc) to give the desired product (Example 75b, 1.05 g, yield 41 %) as yellow oil. LCMS [M+1]+= 164

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 929022-76-4, 2-Chloro-4-fluoronicotinic acid.

Reference:
Patent; FRONTHERA U.S. PHARMACEUTICALS LLC; JIN, Bohan; DONG, Qing; HUNG, Gene; (212 pag.)WO2017/218960; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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