Day: April 6, 2022

Synthetic Route of 623942-84-7 ,Some common heterocyclic compound, 623942-84-7, molecular formula is C7H8BrNO2, 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 a mixture of (3-bromo-6-methoxypyridin-2-yl)methanol (1.9 g, 8.7 mmol) in dichloromethane (100 mL) was added N-bromosuccinimide (1.8 g, 10 mmol) and triphenylphosphine (2.6 g, 10 mmol) under an ice bath condition and nitrogen atmosphere. The reaction mixture was stirred at rt for 3 h and then concentrated in vacuo, the residue was purified by column chromatography on a silica gel eluted with PE/EA (v/v = 30/1) to give the title compound as light yellow liquid (1.4 g, 57 %).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,623942-84-7, its application will become more common.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; WANG, Xiaojun; YANG, Xinye; WU, Junwen; XIONG, Shaohui; PAN, Shengqiang; CAO, Shengtian; ZHANG, Yingjun; (121 pag.)WO2018/24224; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 22282-70-8 ,Some common heterocyclic compound, 22282-70-8, molecular formula is C5H3FIN, 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 75A 2-Amino-4-iodopyridine A mixture of 2-floro-4-iodopyridine (3.0 g, 13.5 mmol), acetylamide (15.8 g, 269 mmol) and potassium carbonate (9.2 g, 67 mmol) was stirred at 180 C. for 7 hours, poured into ice (100 g), extracted with ethyl acetate, washed with brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 50% ethyl acetate/hexane to provide the title compound (1.1 g, 37%). MS (DCI/NH3) m/e 221 (M+H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,22282-70-8, its application will become more common.

Reference:
Patent; Li, Qun; Woods, Keith W.; Zhu, Gui-Dong; Fischer, John P.; Gong, Jianchun; Li, Tongmei; Gandhi, Virajkumar; Thomas, Sheela A.; Packard, Garrick K.; Song, Xiaohong; Abrams, Jason N.; Diebold, Robert; Dinges, Jurgen; Hutchins, Charles; Stoll, Vincent S.; Rosenberg, Saul H.; Giranda, Vincent L.; US2003/187026; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 1256825-86-1, name is Methyl 1H-pyrrolo[2,3-b]pyridine-6-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C9H8N2O2

To a suspension of methyl 1H-pyrrolo[2,3-b]pyridine-6-carboxylate (200 mg; may be prepared as described in intermediate 169) in MeOH (10 ml) was added lithium borohydride (74 mg) and the reaction mixture was stirred at room temperature for 30 min. Lithium borohydride (74 mg) was added and the mixture was heated at 5O0C for 15 hr. Lithium borohydride (148 mg) and the mixture was heated at 5O0C for 24 hr. Lithium borohydride (small amounts portionwise over six hours, approximately 300 mg) was added and the mixture was heated at 5O0C for 72 hr. Lithium borohydride (small amounts portionwise over six hours, approximately 300 mg) was added and the mixture was heated at 5O0C for 24 hr. The reaction mixture was cooled and left at RT for 2 days. The solvent was evaporated and the residue dissolved in aqueous hydrochloric acid (2 N, 20 ml). The aqueous was washed with EtOAc (2 x 30 ml). The aqueous was basified with 12.5 N aqueous sodium hydroxide to pH 14 and then extracted with DCM (3 x 25 ml). The organic layer was dried over magnesium sulfate, filtered and evaporated to give an off-white solid (42mg). This was purified by MDAP to afford the title compound (32 mg) as a white solid. 1H NMR (CD3OD) delta: 4.74 (2H, s), 6.45 (1 H, d), 7.22 (1 H, d), 7.33 (1 H, d), 7.97 (1 H, d). Retention time 0.57 min (LC/MS method 4).

With the rapid development of chemical substances, we look forward to future research findings about 1256825-86-1.

Reference:
Patent; GLAXO GROUP LIMITED; BLUNT, Richard; EATHERTON, Andrew John; GARZYA, Vincenzo; HEALY, Mark Patrick; MYATT, James; PORTER, Roderick Alan; WO2011/12622; (2011); A1;,
Pyridine – Wikipedia,
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. 1111637-94-5, name is 5-Bromo-3-methyl-1H-pyrrolo[2,3-b]pyridine. A new synthetic method of this compound is introduced below., COA of Formula: C8H7BrN2

A solution of 19 (200 mg, 0.952 mmol) and 27 (162.8 mg, 0.952 mmol) in acetonitrile was added Na2CO3 (201.6 mg, 1.904 mmol). The reaction was degassed and purged with nitrogen for 10 min. Pd(dppf)Cl2 (38.8 mg, 0.0476 mmol) was added to the reaction. The reaction mass was degassed and purged with nitrogen for another 10 min. The reaction was heated to 90 C. under sealed conditions overnight, then allowed to cool to RT and diluted with chloroform. The organic layer was filtered through Celite and concentrated to get the crude, which was purified through flash chromatography by using 100-200 silica mesh. The compound was eluted at 2% methanol chloroform as off-white colour solid 28.

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

Reference:
Patent; ARRIEN PHARMACEUTICALS LLC; Vankayalapati, Hariprasad; Yerramreddy, Venkatakrishnareddy; Gangireddy, Paramareddy; Appalaneni, Rajendra P.; US2014/315909; (2014); A1;,
Pyridine – Wikipedia,
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. 156072-84-3, name is 5-Chloro-2-cyano-3-methylpyridine. A new synthetic method of this compound is introduced below., Product Details of 156072-84-3

To a solution of 5-chloro-3-methylpicolinonitrile (24.0 g, 157 mmol) in EtOH (100 mL) was added NaOH 5. ON (110 ml, 550 mmol). The resulting mixture was refluxed at 90 C for 18 h. After cooling to RT, the reaction mixture was conentrated, diluted with water and the pH of the solution was adjusted to 4 by addition of 5N HC1. The solid that precipitated was filtered and set aside. The filtrate was extracted with EtOAc (2X). The aqueous layer was again acidified with 5N HC1 to pH 4 and extracted with EtOAc (2X). The EtOAc extracts were combined, dried, and concentrated. The solid obtained from all the workup steps were combined and dried in a high vac oven at 40 C for 12 h to give the title compound 5-chloro-3-methylpicolinic acid (24.1 g, 140 mmol, 89 % yield). LC/MS (ESf ) m/z = 172.0 (M+H)+; H NMR (400 MHz, CHLOROFORM -J) delta ppm 11.29 (br. s., 1 H), 8.41 (d, J=1.76 Hz, 1 H), 7.73 (d, J=1.76 Hz, 1 H), 2.75 (s, 3 H)

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, 156072-84-3, 5-Chloro-2-cyano-3-methylpyridine.

Reference:
Patent; AMGEN INC.; MINATTI, Ana Elena; LOW, Jonathan, D.; ALLEN, Jennifer, R.; AMEGADZIE, Albert; BROWN, James; FROHN, Michael, J.; GUZMAN-PEREZ, Angel; HARRINGTON, Paul, E.; LOPEZ, Patricia; MA, Vu Van; NISHIMURA, Nobuko; QIAN, Wenyuan; RUMFELT, Shannon; RZASA, Robert, M.; SHAM, Kelvin; SMITH, Adrian, L.; WHITE, Ryan; XUE, Qiufen; WO2014/138484; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 89415-54-3 ,Some common heterocyclic compound, 89415-54-3, molecular formula is C6H8BrN3, 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 mixture of the 5-bromo-/V-methyl-3-nitro-2-pyridinamine (1.14 g, 4.21 mmol assumed). and ammonium chloride (1.103 g, 20.62 mmol) in EtOH^O (8.5 mL of a 1 :1 solution) was stirred as iron (1 .152 g, 20.62 mmol) was added. The mixture was heated to reflux for ~ 2 hours. The mixture was allowed to cool to room temperature then diluted with EtOH and filtered through Celite. The filtrate was concentrated to yield a black tar which was diluted with EtOH then concentrated three times. The residue was slurried in EtOH then filtered. The filtrate was concentrated to yield a black solid which was dissolved in pyridine (15.1 mL). N, N dimethylaminopyridine (0.060 g, 0.49 mmoL) was added followed bybenzenesulfonylchlonde (0.63 mL, 4.91 mmol). The resulting mixture was stirred for one hour under a nitrogen atmosphere. The mixture was then concentrated. The residue diluted with EtOAc, washed with water two times, then saturated NaHC03 followed by brine, dried(Na2S0 ) and concentrated. The residue was purified by silica gel chromatography (0-100% EtOAc in hexanes). Fractions containing the product were combined and concentrated to yield A/-[5-bromo-2-(methylamino)-3-pyridinyl]benzenesulfonamide (0.859 g, 2.51 mmol 60% over 3 steps) as a grey solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 9.58 (br. s., 1 H) 7.94 (br. s., 1 H) 7.75 – 7.64 (m, 3 H) 7.62 – 7.55 (m, 2 H) 6.92 (d, J=2.3 Hz, 1 H) 6.25 (br. s., 1 H) 2.68 (d, J=4.5 Hz, 3 H) LCMS: m/z 344 (M+1 ).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,89415-54-3, its application will become more common.

Reference:
Patent; GLAXOSMITHKLINE LLC; BANKA, Anna, Lindsey; BOTYANSZKI, Janos; DICKERSON, Scott, Howard; DUAN, Maosheng; LEIVERS, Martin, Robert; MCFADYEN, Robert, Blount; MOORE, Christopher, Brooks; REDMAN, Aniko, Maria; SHOTWELL, John, Bradford; TAI, Vincent, W.-F.; TALLANT, Matthew, David; XUE, Jianjun; WO2012/37108; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 914942-88-4, 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 914942-88-4 as follows.

Dichlorobis(triphenylphosphine)rhoalladium (104mg, 0.145mmol) was added in one portion to a mixture of A1.12 (1.Og, 2.48mmol), 3-ethynyl-benzoic acid tert-butyl ester (753mg, 3.72mmol) and triethylamine (10ml) in DMF (7.0ml) at room temperature under a nitrogen atmosphere. The resulting mixture was heated to 90 0C for 50min before cooling to room temperature and evaporating in vacuo. The residue was purified by column chromatography using ethyl acetate:hexane as eluent to give 765mg (65%) of A72.1. Found: M+H = 478.21

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,914942-88-4, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2006/122137; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 887266-57-1, 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.887266-57-1, name is 3-Fluoro-2-hydrazinylpyridine, molecular formula is C5H6FN3, molecular weight is 127.1196, as common compound, the synthetic route is as follows.

This compound is prepared essentially as described in Chem. Ber. (1985) 118:741-752 andFarmaco (1990) 45: 167-186. A mixture of 3,5-diethoxy-penta-2,4-dienoic acid ethyl ester (2.4 g, 11.2 mmol) and (3-fluoro-pyridin-2-yl)hydrazine (1.4 g, 11.0 mmol) in EtOH (30 niL) and concentrated HCl (6 mL) is heated at 900C for 2 hours. The solvent is removed, and the residue is neutralized with saturated NaHCO3 and extracted with DCM. The solution is dried and evaporated, and the residue is column purified (EtOAc:hexane=2: l) to give 103. 1H NMR delta (CDCl3) 1.13 (t, 3H), 3.97 (s, 2H), 4.04 (q, 2H), 6.42 (s, IH), 7.30-7.38 (m, IH), 7.64 (td, IH), 7.72 (s, IH), 8.28 (d, IH).

The chemical industry reduces the impact on the environment during synthesis 887266-57-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; NEUROGEN CORPORATION; WO2006/52546; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 106961-33-5, N,N-Dimethyl-1-(6-methyl-2-(p-tolyl)imidazo[1,2-a]pyridin-3-yl)methanamine, 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: N,N-Dimethyl-1-(6-methyl-2-(p-tolyl)imidazo[1,2-a]pyridin-3-yl)methanamine, blongs to pyridine-derivatives compound. name: N,N-Dimethyl-1-(6-methyl-2-(p-tolyl)imidazo[1,2-a]pyridin-3-yl)methanamine

80 liters of acetone and 8 kg of 2-(4-methyl phenyl)-3-dimethyl amino methyl-6-methyl-[1,2-alpha] imidazo pyridine were taken into a reactor and the mixture was heated to 39 C. The reaction mixture was maintained at 38 to 39 C. for 20 minutes. The reaction mass was then cooled to 26 C. Methyl iodide was pre-cooled to 15 C. and added to the reaction mass under stirring. The reaction mixture was maintained at 27 to 28 C. for 10 hours. Reaction completion was checked using thin layer chromatography. After the reaction was complete, the reaction mass was filtered and the solid was washed with 8 liters of chilled acetone. Into another reactor 60 liters of water and 1.4 kg of sodium cyanide were added. The wet solid obtained above was also added to the reactor and the reaction mass was heated to 84 C. The reaction mixture was maintained at 82 to 84 C. for 12 hours. Reaction completion was checked using high performance liquid chromatography. After the reaction was completed, the reaction mixture was cooled to 55 C. A solution of 12 liters of 48% aqueous sodium hydroxide solution in 40 liters of water was added to the reaction mass. The reaction mixture was heated to 85 C., and maintained for 3 hours. The temperature was slowly raised to 98 C. and maintained under reflux for 13 hours, 30 minutes. Reaction completion was checked using high performance liquid chromatography. After the reaction was complete, the reaction mixture was cooled to 33 C. and filtered through a Celite bed and the bed was washed with 8 liters of water. The filtrate was taken into a fresh reactor and washed with 40 liters of toluene in two equal lots. The pH of the filtrate was adjusted to 5.3 with 14 liters of acetic acid. After completion of the pH adjustment, the filtrate was maintained at 25 C. for 4 hours. The separated solid was filtered and washed with 16 liters of water in two equal lots. The wet solid was dried at 85 C. and a vacuum of 650 mm Hg for 12 hours to yield 5.6 kg of the title compound. (Yield 69.73%) Purity by HPLC: 98.2%.

The synthetic route of 106961-33-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Padi, Pratap Reddy; Bollikonda, Satyanarayana; Jasty, Ananda Mohan; Tamma, Ranga Reddy; Mohanarangam, Saravanan; Yasareni, Sumalatha; Rupakala, Gowri Shanker; Debasish, Ghosh; US2007/27180; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 880870-13-3 , The common heterocyclic compound, 880870-13-3, name is 5-Bromo-2-chloro-4-methoxypyridine, molecular formula is C6H5BrClNO, 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 5-bromo-2-chloro-4-methoxypyridine (5.0 g, 22.48 mmol) in DMF (80 mL) was purged nitrogen for 15 min. Next, Zn(CN)2 (3.96 g, 33.7 mmol) and Pd(Ph3P)4 (2.60 g, 2.25 mmol) were added, successively. The resulting suspension was stirred at 95C for 12 h under nitrogen atmosphere. The reaction mixture was cooled to ambient temperature and filtered to remove inorganic solid. The solvent (DMF) was evaporated to provide the crude residue as an oil, which was purified on silica gel and eluted with 0 – 30% ethyl acetate/hexanes to afford the product. 1HNMR (500 MHz, DMSO- 6) delta 8.69 (s, 1H), 7.50 (s, 1H), 4.04 (s, 3H); LC/MS: [(M+l)]+ = 169.

The synthetic route of 880870-13-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; PASTERNAK, Alexander; PIO, Barbara; CHOBANIAN, Harry, R.; SHI, Zhi-Cai; DONG, Shuzhi; GUO, Yan; WALSH, Shawn, P.; GUO, Zhiqiang; FERGUSON, Ronald, D.; CATO, Brian; (114 pag.)WO2016/60941; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem