Category: pyridine-derivatives

Synthetic Route of 14121-36-9, 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. 14121-36-9, name is 2,3,4,6-Tetrachloropyridine, molecular formula is C5HCl4N, 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.

Step 1: 100g of tetrachloropyridine, 0.5g of catalyst, 15g of acid binding agent,3g of auxiliary agent and 500g of organic solvent are placed in a 1L autoclave, and the autoclave is evacuated three times until the autoclave is in a vacuum state;The tetrachloropyridine is 2,3,4,6-tetrachloropyridine;The catalyst includes a supported activated carbon, a metal M1, a metal M2, and a metal M3 supported on the supported activated carbon,The metal M1 is Pd, the metal M2 is Ag, and the metal M3 is V,The mass percentage content of metal M1 in the catalyst is 2%, and the mass percentage content of metal M2 is 0.4%.The mass percentage of metal M3 is 0.15%; The acid binding agent is triethylamine and urea, and the mass ratio of the triethylamine and urea is 1: 1;The auxiliary is citric acid;The organic solvent is ethyl acetate; Step 2: Replace the high-pressure reactor after vacuuming in Step 1 with nitrogen for three times, and then replace with hydrogen for three times;Step three, continue to introduce hydrogen into the autoclave after the hydrogen replacement in step two, control the hydrogen pressure to 1.0 MPa, the temperature to 50 C., and react for 7 hours under the stirring condition, and reduce to room temperature;Step 4: Drain the hydrogen in the autoclave after the temperature drops to room temperature in Step 3, replace it with nitrogen for three times, filter the system in the autoclave to obtain the filtrate and the recovered catalyst, and reuse the recovered catalyst; Step 5. Distillate the filtrate in step 4 under reduced pressure to obtain 2,3-dichloropyridine as a white solid.The solvent obtained by vacuum distillation is recovered and reused; the vacuum of the vacuum distillation is -0.092 MPaThe temperature of the vacuum distillation was 40 C. The yield of 2,3-dichloropyridine was 98.1%, and the purity was 99.3%.

According to the analysis of related databases, 14121-36-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Xi’an Kaili New Materials Co., Ltd.; Li Xiaoan; Xiao Dawei; Han Bin; Zhang Yu; Zhang Zhixiang; Zeng Yongkang; Wan Kerou; Gao Wu; (13 pag.)CN110759859; (2020); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 22280-60-0, 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. 22280-60-0, name is 6-Chloro-2-methyl-3-nitropyridine. A new synthetic method of this compound is introduced below.

Step 1: 6-Chloro-2-methylpyridin-3-amine (44). To a stirred solution of 43 (5 g, 29 mmol) in EtOH (20 mL) and cone. HCI (20 mL) was added Fe powder (16.2 g, 289 mmole) in small portions at RT over 30 min. Stirring was continued at RT for another 30 min. The solvent was distilled off under reduced pressure. Water was added and the resulting mixture was neutralized with NaHC03. EtOAc was added and the biphasic mixture was filtered through Celite and washed with EtOAc. The phases of the filtrate were separated and the organic layer was washed with water, brine, dried over Na2S04, and concentrated to afford 44 (4.1 g, 99 %) as a yellow solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,22280-60-0, 6-Chloro-2-methyl-3-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; EXELIXIS, INC.; XU, Wei; (106 pag.)WO2017/4608; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 56673-34-8, 3-Bromo-6-mercaptopyridine, 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, name: 3-Bromo-6-mercaptopyridine, blongs to pyridine-derivatives compound. name: 3-Bromo-6-mercaptopyridine

Powdered sodium methoxide (1.08 g, 19.95 mmol) and 1-bromo-3-chloropropane (2.87 mL, 28.7 mmol) were added to a stirred suspension of 5-bromopyridine-2-thiol (3.16 g, 16.63 mmol) in anhydrous methanol (80 mL). The mixture was heated at 60C and stirred under N2 for 1.5 h. After cooling to room temperature, the mixture wasquenched with water-brine (1:1, 100 mL) and extracted with EtOAc (2 x 100 mL). The combined organic fraction was washed with brine (50 mL), then dried (MgSO4) and reduced in vacuo, to give the title compound (3.92 g, 88%) as a yellow solid. H (500 MHz, CDC13) 8.50-8.44 (m, 1H), 7.58 (dd,J8.5, 2.4 Hz, 1H), 7.07 (dd,J8.5, 0.6 Hz, 1H), 3.67 (t,J6.4 Hz, 2H), 3.29 (t,J6.9 Hz, 2H), 2.17 (p,J6.6 Hz, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,56673-34-8, 3-Bromo-6-mercaptopyridine, and friends who are interested can also refer to it.

Reference:
Patent; UCB BIOPHARMA SPRL; ALEXANDER, Rikki Peter; BENTLEY, Jonathan Mark; BRACE, Gareth Neil; BROOKINGS, Daniel Christopher; CHOVATIA, Praful Tulshi; DEBOVES, Herve Jean Claude; JOHNSTONE, Craig; JONES, Elizabeth Pearl; KROEPLIEN, Boris; LECOMTE, Fabien Claude; MADDEN, James; MILLER, Craig Adrian; PORTER, John Robert; SELBY, Matthew Duncan; SHAW, Michael Alan; VAIDYA, Darshan Gunvant; YULE, Ian Andrew; WO2015/86506; (2015); 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. 100202-78-6, name is 2-(Bromomethyl)-6-fluoropyridine, molecular formula is C6H5BrFN, 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. Quality Control of 2-(Bromomethyl)-6-fluoropyridine

General procedure: Hexamethylenetetramine (159 mg, 1.13 mmol, 1.0 eq.) was added under stirring to a solution of 10-6a or 10-6b (1.0 eq.) in chloroform (15 mL). The resulting mixture was stirred at 50C for 1 hour. After cooling to rt, the solvent was removed under reduced pressure. The residue was dissolved with ethanol (10 mL) and concentrated hydrochloric acid (0.5 mL) was added. This mixture was stirred at 50C for 2 hours and at room temperature overnight. The solvent was then evaporated under reduced pressure to give the desired crude products 10a (white solid) or 10b (yellow solid) which were used in the next step without further purification.

With the rapid development of chemical substances, we look forward to future research findings about 100202-78-6.

Reference:
Article; Wenzel, Barbara; Liu, Jianrong; Dukic-Stefanovic, Sladjana; Deuther-Conrad, Winnie; Teodoro, Rodrigo; Ludwig, Friedrich-Alexander; Chezal, Jean-Michel; Moreau, Emmanuel; Brust, Peter; Maisonial-Besset, Aurelie; Bioorganic Chemistry; vol. 86; (2019); p. 346 – 362;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 138891-51-7 ,Some common heterocyclic compound, 138891-51-7, molecular formula is C8H6N2O2, 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.

EXAMPLE 11[2-(6-chloropyridin-3-yl)-4-(2-methoxyethoxy)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)- yl] (imidazo [1,5 -ajpyridin- 1 -yl)methanone (Q-2) O-l (2 g, 6.23 mmol), imidazo[l,5-a]pyridine-l-carboxylic acid (Q-I, 1.112 g,6.86 mmol), EDC (1.315 g, 6.86 mmol), HOBt (0.907 g, 5.92 mmol), and TEA (2.61 mL, 18.70 mmol) were combined in DMF (31 mL) and heated to 60 ºC for 1 hr. Imidazo[l,5-a]pyridine-l- carboxylic acid was prepared according to the literature procedure: Kolar, P.; Petric, A.; Tisler, M.; Felluga, F. J. Heterocycl. Chem. 1991, 7, 1715-1720. The mixture was diluted with EtOAc (100 mL) and washed with sat. aq. NaHCO3 (100 mL), water (100 mL), and brine (100 mL). The organic phase was dried over Na2SO4, filtered, and concentrated in vacuo. The resulting residue was purified by gradient elution on silica gel (0 to 45% [10% MeOH in DCM] in DCM over 50 min to afford the title compound as a white solid (2.43 g, 84%). Data for Q-2: 1H NMR (500 MHz, CDCl3) delta 9.35 (s, IH), 8.61 (d, J= 8.3 Hz, IH), 8.26 (d, J= 9.3 Hz, IH), 8.07 (s, IH), 8.01 (d, J= 6.8 Hz, IH), 7.39 (d, J= 8.3 Hz, IH), 7.03 (t, J= 7.8 Hz, IH), 6.76 (t, J= 6.8 Hz, IH), 4.41-5.60 (vbm, 4H), 4.65 (bs, 2H), 3.81 (bs, 2H), 3.46 (s, 3H), 3.13 (bs, 2H); HRMS m/z (M+H) 465.1426 found, 465.1436 required.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,138891-51-7, its application will become more common.

Reference:
Patent; MERCK SHARP &; DOHME CORP.; BRESLIN, Michael, J.; COLEMAN, Paul, J.; COX, Christopher, D.; RAHEEM, Izzat, T.; SCHREIER, John, D.; WO2010/138430; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 16744-81-3, name is 4-Methoxypicolinaldehyde. This compound has unique chemical properties. The synthetic route is as follows. Formula: C7H7NO2

4-Methoxypicolinaldehyde (1.9 g, 13.85 mmol), methyl carbamimidothioate hemisulfate (1.93 g, 6.93 mmol), ethyl 2-cyanoacetate (1.57 g, 13.85 mmol) and potassium carbonate (2.30 g, 16.63 mmol) were mixed in 95 ml dry EtOH under N2 and heated at 75 0C for two hours. The suspension was cooled to room temperature and solids were filtered. The solids were suspended in 50 ml H2O and stirred for 30 minutes, filtered, and dried overnight to give the desired product as a red solid (1.04 g, 27percent). 1H NMR (400 MHz, DMSO-D6) delta ppm 2.37 (s, 3H), 3.88 (s, 3H), 7.05 (m, IH), 7.43 (d, J=2.54 Hz, IH), 8.45 (d, J=5.66 Hz, IH). MS m/z calculated for (M + H)+ 275.31, found 275.

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, 16744-81-3, 4-Methoxypicolinaldehyde.

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; WO2007/84560; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 3430-22-6, 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. 3430-22-6, name is 3-Bromo-4-methylpyridine, molecular formula is C6H6BrN, 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.

The apparatus was installed, and 3-bromo-4-methylpyridine (13 g, 0.78 mol), Co0.27CuO3 (0.5 g), water was added to the three-necked flask in turn, and the mixture was stirred, and the oil bath was slowly heated to 90 C.Oxygen is initially introduced to maintain the reaction temperature until no oxygen is absorbed under the secondary reaction conditions.The catalyst was filtered off, then slowly added with a NaOH solution to adjust pH = 4, followed by stirring for 10 minutes.There is solid precipitation,The crude product 3-bromoisonicotinic acid was obtained, which was recrystallized from acetone to give a white powdery solid, which was filtered and dried in vacuo.A final yield of 14 g of 3-bromoisonicotinic acid was obtained.The yield was 90%.

According to the analysis of related databases, 3430-22-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Dalian Jindian Biological Technology Co., Ltd.; Jin Feng; (5 pag.)CN109851551; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1111637-94-5, 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. 1111637-94-5, name is 5-Bromo-3-methyl-1H-pyrrolo[2,3-b]pyridine, molecular formula is C8H7BrN2, 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 5-bromo-3-methyl-lH-pyrrolo[2,3-b]pyridine (20 g, 94.8 mmol) in NN-dimethylformamide (200 mL) was added potassium acetate (27.9 g, 284.4 mmol) and 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(l,3,2-dioxaborolane) (28.8 g, 113.74 mmol). The resulting mixture was degassed with nitrogen for 5 min, l,l’-Bis(diphenylphosphino)ferrocene-palladium(n)dichloride (6.65g, 9.48mmol) was added and the mixture was degassed with nitrogen once more for 5 min. The reaction mixture was stirred overnight at 80-90 C. The reaction mixture was poured into water, extracted with (3 x 200 mL). The combined organic layers were washed with brine, dried over sodium sulfate and concentrated to dryness in vacuo. The resulting residue was purified by column chromatography (silica gel, 100-200 mesh, 9% to 50% ethyl acetate in petroleum ether) affording 3-methyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-pyrrolo[2,3-b]pyridine as a white solid (10.5 g, 43%): NMR (400MHz, DMSO-d6), delta 11.360 (s, 1H), 8.371-8.375 (d, /= 1.6 Hz, 1H), 8.097-8.100 (s, /= 1.2 Hz, 2H), 7.17 (s, 1H), 3.296 (s, 3 H), 1.245 (s, 12H).

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 1111637-94-5, 5-Bromo-3-methyl-1H-pyrrolo[2,3-b]pyridine.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; ESTRADA, Anthony; LIU, Wen; PATEL, Snahel; SIU, Michael; WO2014/111496; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 327056-62-2, 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 327056-62-2, name is 2-Cyano-5-fluoropyridine. This compound has unique chemical properties. The synthetic route is as follows.

A solution of 2-cyano-5-fluoropyridine (0.65 g, 5.3 mmol) in sodium methoxide (1.83 mL of 25% wt. solution in methanol, 7.95 mmol) was stirred at 0 C. for 1.5 hours and 2 hours at ambient temperature. The reaction was then diluted with ethyl acetate and washed with water and brine. Removal of the solvent in vacuo afforded 304 mg (43%) of 2-cyano-5-methoxypyridine.

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 327056-62-2, 2-Cyano-5-fluoropyridine.

Reference:
Patent; Wagenen, Bradford Van; Stormann, Thomas M.; Moe, Scott T.; Sheehan, Susan M.; McLeod, Donald A.; Smith, Daryl L.; Isaac, Methvin Benjamin; Slassi, Abdelmalik; US2003/55085; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1289131-55-0, 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 1289131-55-0, name is 4-Bromo-2-(2-methoxyethoxy)pyridine. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 4-bromo-2-(2-methoxyethoxy)pyridine (for a preparation see Intermediate 37, 306 mg, 1.319 mmol), 5/s(pinacolato)diboron (1004 mg, 3.96 mmol), PdCI2(dppf) (96 mg, 0.132 mmol) and potassium acetate (388 mg, 3.96 mmol) in 1 ,4-dioxane (10 mL) was heated in a microwave at 100C for 30 min. The reaction was diluted with ethyl acetate and filtered through a Celite column. The filtrate was evaporated to give 2-(2-methoxyethoxy)-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2- yl)pyridine as a brown residue. The yield was assumed to be 100 % (368 mg, 1.319 mmol). The material was used crude in the next stage without further purification. LCMS (2 min, Formic): Rt = 0.44 min, MH+ 198 (observed mass ion is consistent with hydrolysis to boronic acid under LCMS conditions).

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 1289131-55-0, 4-Bromo-2-(2-methoxyethoxy)pyridine.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; AMANS, Dominique; BAMBOROUGH, Paul; BARKER, Michael David; BIT, Rino Antonio; BROWN, John Alexander; CAMPBELL, Matthew; GARTON, Neil Stuart; LINDON, Matthew J; SHIPLEY, Tracy Jane; THEODOULOU, Natalie Hope; WELLAWAY, Christopher Roland; WESTAWAY, Susan Marie; WO2014/140077; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem