Day: April 13, 2022

Synthetic Route of 956010-87-0, Adding some certain compound to certain chemical reactions, such as: 956010-87-0, name is 3-(Trifluoromethyl)-1H-pyrazolo[3,4-b]pyridine,molecular formula is C7H4F3N3, 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 956010-87-0.

Trifluoroacetic anhydride (2.6 mL, 18.7 mmol) was added to a solution of tetrabutylammonium nitrate (5.7 g, 18.7 mmol) in dichloromethane (50 mL) cooled to 00C in an ice bath. After 5 minutes, 3-(trifluoromethyl)-lH-pyrazolo[3,4-b]pyridine (0.5 g, 2.67 mmol) was added portionwise. The resulting solution was stirred at room temperature overnight. The reaction mixture was treated with saturated aqueous sodium bicarbonate, and the layers were separated. The aqueous layer was extracted with dichloromethane. The combined organic layers were washed with saturated aqueous sodium bicarbonate, dried over magnesium sulfate, filtered, and evaporated to an oil. The crude product was purified by column chromatography, eluting with hexanes/ethyl acetate (2:1) to give 5-nitro-3-(trifIuoromethyl)-lH-pyrazolo[3,4- b]pyridine (0.19 g, 31%) as a solid.

According to the analysis of related databases, 956010-87-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARRAY BIOPHARMA INC.; GENENTECH, INC.; GRADL, Stefan; LAIRD, Ellen; MORENO, David; REN, Li; WENGLOWSKY, Steven Mark; WO2011/25968; (2011); 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 1137-67-3, name is 2-(Pyridin-3-yl)-1H-benzo[d]imidazole. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C12H9N3

CdSO4·3/8 H2O (0.026 g, 0.1 mmol), 3PBI (0.0195 g, 0.1 mmol), NaOH (0.0072 g,0.18 mmol), adipic acid (0.0146 g, 0.1 mmol), and water (6 mL) were added to a 15-mLTeflon reactor and heated under autogenous pressure at 160 C for 3 days. The reaction mixture was cooled to room temperature at a rate of 5 C h-1. Yellow pellet crystals of 3suitable for X-ray diffraction analysis were obtained (0.0123 g, yield: 27% based onCdSO4). Elemental analysis Calcd (%) for C18H15Cd N3O5 (465.73): C, 46.38; H, 3.22; N,9.02; found: C, 46.19; H, 3.24; N, 9.05. IR (KBr, cm-1): 2943(w), 1557(s), 1419(s), 1329(m), 1278(m), 1197(m), 1130(w), 1049(m), 962(m), 930(m), 816(m), 740(s), 700(m), 637(m), 519(w), 428(m).

With the rapid development of chemical substances, we look forward to future research findings about 1137-67-3.

Reference:
Article; Wang, Cui-Cui; Wang, Jin-Hua; Tang, Gui-Mei; Wang, Yong-Tao; Cui, Yue-Zhi; Ng, Seik Weng; Journal of Coordination Chemistry; vol. 68; 21; (2015); p. 3918 – 3931;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 6200-59-5, 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. 6200-59-5, name is Imidazo[1,2-a]pyridine-3-carbonitrile, molecular formula is C8H5N3, 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.

A solution of sodium methoxide (prepared from sodium (0.13 g, 5.65 mmol) and methanol (10 mL)) was added dropwise to a suspension of imidazo[1 ,2-a]pyridine-3- carbonitrile (4.0 g, 27.94 mmol) in methanol (15 mL) and the resulting mixture was stirred at ambient temperature overnight. Ammonium chloride (1 .64 g, 30.7 mmol) was then added and the mixture was heated at 90 C for 4h. The solvent was removed under reduced pressure and the resulting solid was treated with diethyl ether, filtered and purified by flash chromatography (dichloromethane/ ethanol) to give the title compound (4.47 g, 99%) as a white solid. LRMS (m/z): 161 (M+1 )+ 1H NMR delta (300 MHz, DMSO-d6): 7.21 (t, 1 H), 7.56 (t, 1 H), 7.79 (d, 1 H), 8.26 (s, 1 H), 8.67 (d, 1 H) .

According to the analysis of related databases, 6200-59-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALMIRALL, S.A.; BACH TANA, Jordi; PEREZ CRESPO, Daniel; LLERA SOLDEVILA, Oriol; ESTEVE TRIAS, Cristina; TABOADA MARTINEZ, Lorena; WO2015/91531; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1156542-30-1 , The common heterocyclic compound, 1156542-30-1, name is 2-Bromo-5-fluoro-4-(trifluoromethyl)pyridine, molecular formula is C6H2BrF4N, 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 20 mL pressure vial was added (5 -2-amino-2,4-dimethylpentan-l-ol (323 mg, 2.462 mmol) and 2-bromo-5-fluoro-4-(trifluoromethyl)pyridine (601 mg, 2.462 mmol) in tetrahydrofuran (3.3 mL) to give a tan solution. Potassium tert- butoxide (2.95 mL, 2.95 mmol) (1.0 M in THF) was added dropwise under nitrogen. After 5 min stirring at rt, the vial was sealed and the mixture was stirred at 80 C for 18 h. The mixture was partitioned between water and EtO Ac. The layers were separated. The aqueous layer was extracted with EtO Ac. The combined organic solution was washed with brine, dried and concentrated to a tan oil. The crude was purified by silica gel chromatography up to 10% MeOH/CEhCh to afford (Patent; BRISTOL-MYERS SQUIBB COMPANY; BRONSON, Joanne J.; CHEN, Ling; DITTA, Jonathan L.; DZIERBA, Carolyn Diane; JALAGAM, Prasada Rao; LUO, Guanglin; MACOR, John E.; MAISHAL, Tarun Kumar; NARA, Susheel Jethanand; RAJAMANI, Ramkumar; SISTLA, Ramesh Kumar; THANGAVEL, Soodamani; (485 pag.)WO2017/59085; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 7477-10-3, 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 7477-10-3 as follows.

To a suspension of 49.0 g (0.27 mol) 6-hydroxy-5-nitro-nicouenic acid in thionyl chloride (240 mi) are added 2 ml of DMF. This mixture is stirred at 60C until the evolution of gaz has ended. Then it is stirred at 80C for further 18 h. Residual thionyl chloride is removed under vacuo and the resulting residue is coevaporated three times with toluene. Subsequently this reaction mixture is dissolved in dichloromethane (100 mi) and cooled to 0C before methanol (55.5 ml) is dropwise added. The precipitated solid is filtered off and dried under vacuo at 50C to give 27.6 g (13.7 mmol/52 %) of the title compound as a light yellow solid with a melting point of 78C (dichloromethane/methanol).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,7477-10-3, its application will become more common.

Reference:
Patent; ALTANA PHARMA AG; WO2005/77947; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 73112-16-0 ,Some common heterocyclic compound, 73112-16-0, molecular formula is C6H5Br2N, 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.

Preparative Example 3 – Tert-butyl (6-bromo-4-methylpyridin-2-yl)carbamate (PrepEx-3)[00186] Into a flask were added tert-butyl carbamate (5.6 g, 47.8 mmol) and 2,6-dibromo-4-methyl-pyridine (12 g, 47.8 mmol) followed by degassed 2-MeTHF (120 mL). Solid sodium tert-butoxide (4.6 g, 47.8 mmol) was then added followed bytris(dibenzylideneacetone)dipalladium(0) (1.1 g, 1.2 mmol) and l,l’-bis(di-tert- butylphosphino)ferrocene (1.1 g, 2.4 mmol), and the solution evacuated and refilled with nitrogen 3 times. The solution was heated to 70 C for 4 h and then cooled to rt. The mixture was treated with water (20 mL) and EtOAc (100 mL) and filtered through Celite. The organic solution was washed with brine (100 mL) and then concentrated under reduced pressure. The resulting residue was purified via silica gel chromatography to afford tert-butyl (6-bromo-4- methylpyridin-2-yl)carbamate (11.2 g, 82%) as a white solid. MS ESI calcd for CnH15BrN202 [M + H]+ 287, found 287. 1H NMR (600 MHz, CDC13) delta 7.70 (s, 1H), 7.13 (s, 1H), 6.95 (s, 1H), 2.29 (s, 3H), 1.49 (s, 9H) ppm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,73112-16-0, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ROMEO, Eric Thomas; MACHACEK, Michelle, R.; TROTTER, Benjamin Wesley; MILLER, Thomas Allen; ANDRESEN, Brian Michael; ANTHONY, Neville John; TAOKA, Brandon, M.; LIU, Yuan; WO2012/151137; (2012); 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. 700811-29-6, name is 2-Chloro-4-hydrazinopyridine. A new synthetic method of this compound is introduced below., Safety of 2-Chloro-4-hydrazinopyridine

A solution of (2-chloro-pyridin-4-yl)-hydrazine (1.0 g, 6.965 mmol), ethyl 2-(ethoxymethylene)-4,4,4-trifluoro-3-oxobutanoate, INT1 (1.67 g, 6.965 mmol) and triethylamine (1.92 mL, 13.758 mmol) in ethanol (25 mL) was stirred overnight at 80 C. The reaction mixture was concentrated under reduced pressure and residue purified by chromatography over silica gel (gradient of EA in heptane from 0 to 25%) to afford the title compound as a clear oil (765 mg, 34%). 1H NMR (300 MHz, chloroform-d) delta 1.39 (t, J=7.2 Hz, 3H), 4.39 (q, J=7.2 Hz, 2H), 7.26 (s, OH), 7.36 (d, J=5.5 Hz, 1H), 7.51 (d, J=1.9 Hz, 1H), 8.16 (s, 1H), 8.57 (d, J=5.4 Hz, 1H). MS m/z 320 (MH+).

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, 700811-29-6, 2-Chloro-4-hydrazinopyridine.

Reference:
Patent; Janssen Pharmaceutica NV; Lu, Tianbao; Connolly, Peter J.; Cummings, Maxwell David; Barbay, Joseph Kent; Kreutter, Kevin D.; Wu, Tongfei; Diels, Gaston Stanislas Marcella; Thuring, Jan Willem; Philippar, Ulrike; Edwards, James Patrick; Shen, Fang; (202 pag.)US2019/381019; (2019); 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. 60154-05-4, name is 5-Iodo-1-methylpyridin-2(1H)-one. A new synthetic method of this compound is introduced below., Formula: C6H6INO

Into a 2 L 4-necked, round-bottom flask, purged and maintained with an inert atmosphere of N2, was placed a solution of 5-[(tert-butyldimethylsilyl)oxy]-1H-indazole (805 g, 3.2mol) in toluene (8 L), 5-iodo-1-methyl-1,2-dihydropyridin-2-one (800 g, 3.4 mol) and K3P04 (1.2 kg, 5.8 mol). Cyclohexane-1,2-diamine (63 g, 0.5 mol) was added followed by the addition of Cul (1.3 g, 6.8 mmol) in several batches. The resulting solution was stirred overnight at 102C. The resulting mixture was concentrated under vacuum to yield 3.0 kg of the title compound as a crude black solid. LC/MS: mlz 356 [M+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, 60154-05-4, 5-Iodo-1-methylpyridin-2(1H)-one.

Reference:
Patent; ASTRAZENECA; RIPA, Lena, Elisabeth; LAWITZ, Karolina; LEPISTOe, Matti, Juhani; HEMMERLING, Martin; EDMAN, Karl; LLINAS, Antonio; (96 pag.)WO2016/46260; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.1211523-71-5, name is 2-(2-Bromopyridin-3-yl)acetonitrile, molecular formula is C7H5BrN2, molecular weight is 197.03, as common compound, the synthetic route is as follows.SDS of cas: 1211523-71-5

To a 0C solution of 2-(2-bromopyridin-3-yl)acetonitrile (2.21 g, 11.21 mmol) inDMF (20 mL) was added NaH (60% dispersion in mineral oil, 1.12 g, 28.03 mmol) in portions. The resulting mixture was warmed to 60 C and stirred for 1.5 h. Tert-butylbis(2-chloroethyl)carbamate (3.26 g, 13.46 mmol) was added to the mixture and stirred for 2 h at 60 C. After cooling to RT, the reaction mixture was quenched with brine (50 mL), extracted with EA (3 x 100 mL). The combined organic layers were washed with brine (3 x 80 mL), dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica chromatography (eluting with EA: Hex = 1: 3, v/v) to give tert-butyl4-(2-bromopyridin-3-yl)-4-cyanopiperidine-1-carboxylate (1.56 g). MS: m/z 366 (M+H) .

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1211523-71-5, 2-(2-Bromopyridin-3-yl)acetonitrile, and friends who are interested can also refer to it.

Reference:
Patent; JACOBIO PHARMACEUTICALS CO., LTD.; JACOBIO-ALPHA PHARMACEUTICALS CO., LTD.; MA, Cunbo; GAO, Panliang; HU, Shaojing; XU, Zilong; HAN, Huifeng; WU, Xinping; KANG, Di; LONG, Wei; (202 pag.)WO2018/172984; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 120739-77-7 ,Some common heterocyclic compound, 120739-77-7, molecular formula is C8H11ClN2, 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 100ml three necked round bottom flask was added N-((6-chloropyridin-3-yl)methyl)ethanamine (17.0 g, 0.1 mol), (2-nitroethene-1,1-diyl)bis(methylsulfane) (15.0 g, 0.09 mol), dry ethanol (50 mL). The mixture was refluxed. After completion, the reaction mixture was cooled to r.t. and concentrated under reduced pressure to obtain crude product as oil, which was purified by column chromatography to afford 5.3g N-((6-chloropyridin-3-yl)methyl)-N-ethyl-1- (methylthio)-2-nitroethenamine in 18.5% yield. GC-MS: m/z (%) = 242 ([M]+-46, 53), 227 (15), 213 (100), 169 (45), 155 (28), 141 (29), 126 (91),90 (12).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,120739-77-7, its application will become more common.

Reference:
Patent; East China University of Science and Technology; Shanghai Shengnong Pesticide Co., Ltd.; EP2377845; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem