Pyridine-derivatives

Application of 171178-45-3, 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 171178-45-3, name is tert-Butyl (6-chloropyridin-3-yl)carbamate. This compound has unique chemical properties. The synthetic route is as follows.

Step 2: Preparation of tert-butyl 6-chloro-4-fluoropyridin-3-ylcarbamate To a -63 C. solution of tert-butyl 6-chloropyridin-3-ylcarbamate (24.99 g, 109.3 mmol) and TMEDA (39 mL, 260.0 mmol, Aldrich) in diethyl ether (700 mL) was added a 1.6M n-butyl lithium solution in hexane (193 mL, 308.8 mmol, Aldrich) over a period of 30 minutes while maintaining the temperature of the reaction at -60 to -50 C. The reaction was stirred at -60 C. for an additional 10 minutes after the addition was complete then warmed to -10 C. and stirred at -25 to -10 C. for 2.0 hours. The reaction was cooled to -60 C. and a solution of N-fluorobenzenesulfonimide (53.49 g, 169.6 mmol, Aldrich) in tetrahydrofuran (155 mL) was added while keeping the temperature below -50 C. It precipitated on addition and stirring became difficult. The reaction was then allowed to slowly warm to 0 C. over 1 hour. The reaction was quenched with saturated ammonium chloride solution (400 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (2×250 mL). The combined organic layers were washed with brine, dried over magnesium sulfate, and solvent was removed at reduced pressure to give an oily brown solid. The material was passed through a column of silica gel with 20% ethyl acetate/hexane. The 6-chloro-4-fluoropyridin-3-ylcarbamate was obtained as a yellow solid. (15.88 g, 59% yield). 1H NMR (CDCl3) delta 9.09 (1H), 7.12 (1H), 6.55 (1H), 1.54 (s, 9H).

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 171178-45-3, tert-Butyl (6-chloropyridin-3-yl)carbamate.

Reference:
Patent; Pfizer Inc; US2007/249615; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 168173-56-6 ,Some common heterocyclic compound, 168173-56-6, molecular formula is C6H5BrClN, 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: 4-Amino-5,5-disubstituted furan-2(5H)-one 1a-e (2 mmol) was dissolved in dry MeCN (25 mL) in a 50-mL round-bottom flask. The solution was cooled to 0 C by an ice-water bath, then Cs2CO3 (1.304 g, 4 mmol) was added slowly. The mixture was warmed to r.t. and stirred for 4 h. ArCH2Cl 2a-h (2.4 mmol) was added and the mixture was stirred for 12 h under reflux. The mixture was cooled to r.t. and the solid material was filtered off. The filtrate was concentrated in vacuo and the crude product was purified by flash column chromatography (silica gel, 200-300 mesh, petroleum/EtOAc 4:1 to 3:2) to give compounds 3a-x and 4a-f.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,168173-56-6, its application will become more common.

Reference:
Article; Yu, Zhao; Xinlei, Liu; Weiwei, Wang; Rui, Geng; Wang, Mingan; Synthesis; vol. 50; 20; (2018); p. 4055 – 4062;,
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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. 55240-51-2, name is 2-Phenylisonicotinic acid. A new synthetic method of this compound is introduced below., Safety of 2-Phenylisonicotinic acid

General procedure: To a solution of cyanoacetic acid (340 mg, 4.0 mmol) and 1,1-dioxo-1H-1lambda6-benzo[b]thiophen-6-ylamine (362 mg, 2.0 mmol) in 10 mL of CH2Cl2 was added DIPEA (774 mg, 6.0 mmol). HBTU (1.14 g, 3.0 mmol) was added at 0 C. The resulting mixture was stirred at r.t. for 28 h. The reaction mixture was diluted with CH2Cl2 (80 mL) and washed with water (20 mL). The organic layer was separated and dried with anhydrous Na2SO4. The solution was concentrated to give a crude product, which was purified with silica gel column (EtOAc/hexane = 1/1) to obtain the desired product (400 mg, 81%) as a yellow solid (mp 207-208 C). HPLC purity 98.6% (tR = 10.93 min). 1H NMR (600 MHz, DMSO-d6) delta 10.79 (s, 1H), 8.04 (s, 1H), 7.67-7.69 (m, 1H), 7.60 (d, 1H, J = 7.2 Hz), 7.57 (d, 1H, J = 7.8 Hz), 7.30 (d, 1H, J = 7.2 Hz), 3.98 (s, 2H). 13C NMR (150 MHz, DMSO-d6) delta 162.0, 140.7, 137.3, 132.8, 130.3, 126.7, 126.1, 123.4, 115.6, 111.4, 27.0. HRMS (ESI) calcd for C11H19N2O3S 249.0328 (M + H)+, found 249.0330.

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, 55240-51-2, 2-Phenylisonicotinic acid.

Reference:
Article; Chen, Haijun; Yang, Zhengduo; Ding, Chunyong; Chu, Lili; Zhang, Yusong; Terry, Kristin; Liu, Huiling; Shen, Qiang; Zhou, Jia; European Journal of Medicinal Chemistry; vol. 62; (2013); p. 498 – 507;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 65515-28-8, name is Methyl 2,6-dichloronicotinate, the common compound, a new synthetic route is introduced below. Recommanded Product: 65515-28-8

A solution of 2,6-dichloronicotinic acid methyl ester (2.39 g, 11.6 mmol) and NaOMe (800 rog, 14.06 mmol) in THF (15 mL) was stirred at ambient temperature for 3 days. The reaction mixture was quenched by adding 10 mL of 10% NH4Cl solution and extracted with ether. The combined organic layers was dried over anhydrous Na2SO4 and concentrated to afford an unseparable mixture (1.7 g), containing 6-chloro-2-methoxynicotinic acid methyl ester.

The synthetic route of 65515-28-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; XENON PHARMACEUTICALS INC.; WO2006/14168; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 55304-73-9, 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. 55304-73-9, name is 2,6-Dichloro-3-formylpyridine. A new synthetic method of this compound is introduced below.

2,6-Dichloronicotinaldehyde (500 mg, 2.84 mmol) was diluted with dimethylamine (3125 muL, 6.25 mmol) and heated to 500C. After stirring for 3 hours, the reaction was loaded onto a silica gel column and eluted with 5% ethyl acetate/hexanes to 50% ethyl acetate/hexanes to yield 6-chloro-2-(dimethylamino)nicotinaldehyde (155 mg, 0.840 mmol, 29.6 % yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,55304-73-9, its application will become more common.

Reference:
Patent; ARRAY BIOPHARMA INC.; COOK, Adam; HUNT, Kevin, W.; DELISLE, Robert Kirk; ROMOFF, Todd; CLARK, Christopher, T.; KIM, Ganghyeok; CORRETTE, Christopher, P.; DOHERTY, George, A.; BURGESS, Laurence, E.; WO2010/75200; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1594-57-6 ,Some common heterocyclic compound, 1594-57-6, molecular formula is C6H7N3O, 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: a) To a mixture of the carboxylic acid (5 mmol) in acetone (20 mL) was added EDC (5.5 mmol). The reaction mixture was stirred at room temperature for 30 min, then the amidoxime (5 mmol) was added. The resulting mixture was stirred at room temperature for 12 h. Acetone was evaporated at reduced pressure and to the residue was added water (100 mL). The resulting precipitate was filtered off, washed with water (50 ml) and dried under vacuum at rt.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1594-57-6, its application will become more common.

Reference:
Article; Baykov, Sergey; Sharonova, Tatyana; Osipyan, Angelina; Rozhkov, Sergey; Shetnev, Anton; Smirnov, Alexey; Tetrahedron Letters; vol. 57; 26; (2016); p. 2898 – 2900;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 109-04-6, 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 109-04-6 as follows.

To a solution of 2-bromopyridine (XCIII) (10 g, 63 mmol, 1.00 eq) in THF (150 mL) was added n-BuLi (25.3 mL, 63 mmol, 1.00 eq) and the mixture was stirred at -70C for 30 mm under nitrogen atmosphere. Then n-Bu3SnCl (21.7 g, 67 mmol, 1.06 eq) was added and the mixture was stirred at the same temperature for another 2 h. Saturated ammonium chloride solution (150 mL) was added to the solution and extracted with EtOAc (150 mL x 3). The combined organic layers were dried over Na2504, filtered and concentrated in vacuo to afford the crude 2-(tributylstannyl)pyridine (XCIV) (25.9 g, 63 mmol, 100% yield) as a yellow oil. The crude product was used without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,109-04-6, its application will become more common.

Reference:
Patent; SAMUMED, LLC.; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; MARAKOVITS, Joseph Timothy; BOLLU, Venkataiah; HOOD, John; (307 pag.)WO2017/23989; (2017); A1;,
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Pyridine | C5H5N – PubChem

Reference of 15862-30-3, 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.15862-30-3, name is 3-Bromo-5-nitropyridine, molecular formula is C5H3BrN2O2, molecular weight is 202.99, as common compound, the synthetic route is as follows.

To a flask was added 3-bromo-5-nitropyridine (60 mg, 296 mumol), THF (2 mL), tert-butyl pent-4-yn-1-ylcarbamate (59.6 mg, 325 mumol), Pd(OAc)2 (3.32 mg, 14.8 mumol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (17.1 mg, 29.6 mumol) and Cs2CO3 (193 mg, 591 mumol). Then the mixture was bubbled with N2 for 5 mins and heated to reflux (70 C. oil bath) for about 4.5 hours. The mixture was filtered through celite and the filtrate was concentrated to give a brown solid. After purification via combiflash (eluted with EA/PE=020%40%), tert-butyl N-[5-(5-nitro-3-pyridyl)pent-4-ynyl]carbamate (Compound 72A) was obtained as pale brown oil.

Statistics shows that 15862-30-3 is playing an increasingly important role. we look forward to future research findings about 3-Bromo-5-nitropyridine.

Reference:
Patent; Hoffmann-La Roche Inc.; Hoves, Sabine; Wang, Lisha; Yun, Hongying; Zhang, Weixing; Zhu, Wei; (58 pag.)US2016/257653; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 54916-66-4, 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. 54916-66-4, name is 5-Bromo-2-methoxynicotinic acid, molecular formula is C7H6BrNO3, 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-2-methoxynicotinic acid (15 g, 64.6 mmol, commercially available from, for example, Combiblocks) in DCM (100 mL) cooled to 0 0C, was added oxalyl dichloride (16.98 mL, 194.0 mmol) followed by the slow addition of DMF (5.01 mL, 64.6 mmol) at 0 C. The reactionmixture was then stirred for 18 h at rt. A small aliquot of the reaction mixture was taken and quenched with MeOH, the TLC shows the complete conversion of SM. The reaction mixture was then concentrated and re-dissolved in DCM (150 mL) and treated with ethanamine hydrochloride (7.91 g, 97 mmol). The reaction mixture was stirred for 3 h at rt. After the reaction, water was added andthe organics extracted with ethyl acetate (2 x 300 mL). The organic layer was separated, dried over Na2504, filtered and concentrated to obtain the crude product. The crude product was purified by column chromatography on a silica gel 100-200 column and was eluted with l6% EtOAc/n-hexane. The collected pure fractions were concentrated under reduced pressure to afford the desired product 5-bromo-N-ethyl-2-methoxynicotinamide (11 g, 41.0 mmol, 64 % yield) as an off-whitesolid.LCMS (10 mm RND-FA-10-MIN): Rt = 4.22 mi [MH] = 261.LCMS Conditions: RND-FA- lO-MIN:Column: Acquity BEH C18 (100 mm x 2.1 mm, 1.7 pm)Mobile Phase: A: 0.05% formic acid in ACN; B: 0.05% formic acid in waterTime (mm) /%B: 0/97, 0.4/97, 7.5/2, 9.5/2, 9.6/97, 10/97Column Temp: 35 C, Flow Rate: 0.45 mL/min

According to the analysis of related databases, 54916-66-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; ATKINSON, Stephen John; AYLOTT, Helen Elizabeth; COOPER, Anthony William James; DEMONT, Emmanuel Hubert; HARRISON, Lee Andrew; HAYHOW, Thomas George Christopher; LINDON, Matthew J; PRESTON, Alexander G; SEAL, Jonathan Thomas; WALL, Ian David; WATSON, Robert J; WOOLVEN, James Michael; (308 pag.)WO2017/37116; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 14237-71-9, 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 14237-71-9, name is 2-Chloro-4,6-dimethylnicotinonitrile. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: In a 100 mL round bottom flask, compound 2a (0.7 g, 4.0 mmol),P-methylaniline (1.3 g, 12.0 mmol) and DMSO (15 mL) were stirred and heated in an oil bath at 120 under N2 protection(The progress of the reaction was monitored by TLC, developing solvent: ethyl acetate: petroleum petroleum = 1: 10). After the reaction is completed, cool to room temperature.Extract with saturated NaHCO3 solution (3 × 30 mL) and DCM solution (5 × 30 mL), combine the organic phases,Wash with saturated NaCl solution 3 ~ 4 times, dry with anhydrous Na2SO4, and concentrate under reduced pressure.Purification by silica gel column chromatography (eluent: V ethyl acetate: V petroleum ether = 1: 45) to obtain compound 3aa as a white powder. Yield: 39%.

According to the analysis of related databases, 14237-71-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Guilin Medical University; Huang Wanyun; Zhang Xiaoting; Zheng Bin; Lv Liang; Wang Shuqin; (17 pag.)CN110305128; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem