Pyridine-derivatives

Related Products of 407-20-5, 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 407-20-5 as follows.

Preparation 10: (l-(3-amino-5-fluoropyridin-4-yl)piperidin-4-yl)(4-methylpiperazin-l- yl)methanone (hydrochloride) 17b Scheme 5 Step 1: 3-bromo-4-chloro-5-fluoropyridine hydrochloride 18 [00261] To a solution of diisopropylamine (6.899 g, 9.555 mL, 68.18 mmol) in THF (75 mL) cooled to -78C, was added butyllithium (25 mL of 2.5 M in hexanes, 62.5 mmol). The reaction mixture was allowed to warm to -20C then cooled back down to -78C. A solution of 3-bromo-5-fluoro-pyridine (10 g, 56.82 mmol) in THF (25 mL) was added dropwise keeping temperature below -70C (approx 30 mins). The reaction mixture was stirred at – 78C for 30 min and a solution of 1, 1, 1,2,2,2-hexachloroethane (14.8 g, 62.5 mmol) in THF (20 mL) was then added dropwise, keeping temperature below -70C (over approximately 30 mins). The mixture was stirred at -78C for 20 minutes, allowed to warm to room temperature, cooled back to 0C and quenched with water (100 rnL). EtOAc (400 mL) was then added, and organic layer separated, washed with water (2x), brine (lx), dried (MgS04), filtered and concentrated in vacuo to leave a brown solid. The solid was triturated in pentane (lOOmL) for 10 minutes, then filtered. The filtrate was concentrated in vacuo to afford product as a brown oil that turned to a crystalline solid on standing, 1 1.85 g, 89%). lH NMR (DMSO-d6) delta 8.78 (s, 1H), 8.76 (s, 1H). [00262] To a solution of 3-bromo-4-chloro-5-fluoro-pyridine (7.56 g, 32.18 mmol) in pentane (100 mL) was added hydrogen chloride (2M in ether) (17.7 mL of 2 M, 35.4 mmol). An off-white precipitate formed instantly. The mixture was stirred for 5 minutes then the solid was collected by filtration, washed with pentane and dried by suction to afford the desired product as an off-white solid (4.79 g, 60%). XH NMR (DMSO-d6) delta 8.77 (s, 1H), 8.75 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,407-20-5, its application will become more common.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; CHARRIER, Jean-Damien; DAVIS, Chris; DURRANT, Steven; JARDI, Gorka, Etxebarria I; FRAYSSE, Damien; KAY, David; KNEGTEL, Ronald; PIERARD, Francoise; PINDER, Joanne; STORCK, Pierre-Henri; WO2014/143240; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 70201-42-2, 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. 70201-42-2, name is 3,5-Dibromoisonicotinaldehyde, molecular formula is C6H3Br2NO, 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.

3,5-Dibromoisonicotinaldehyde (80 g, 303 mmol), followed by cesium carbonate (98 g, 302 mmol) was added to a 2 L round bottom flask containing THF (1.3 L) under N2. Methyl mercaptoacetate (32 g, 302 mmol) was added and the mixture was heated at 60 C overnight. After cooling to rt, ethyl acetate was added and the organic layer was washed with water, aqueous saturated NaHCO3, solution, and brine, then dried over and filtered to give a white solid The crude product was purified by recrystallization from ethyl acetate to give the desired product (60 g, 73%).

According to the analysis of related databases, 70201-42-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GENENTECH,INC.; FORMA TM, LLC; BAIR, Kenneth W.; BAUMEISTER, Timm R.; BUCKMELTER, Alexandre J.; CLODFELTER, Kanl H.; DRAGOVICH, Peter; HAN, Bingsong; LIN, Jian; LIU, Xiongcai; REYNOLDS, Dominic J.; SMITH, Chase C.; WANG, Zhongguo; YUEN, Po-Wai; ZAK, Mark; ZHANG, Yamin; ZHENG, Xiaozhang; ZHAO, Guiling; WO2013/127268; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 73998-95-5, Adding some certain compound to certain chemical reactions, such as: 73998-95-5, name is (4,6-Dichloropyridin-3-yl)methanol,molecular formula is C6H5Cl2NO, 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 73998-95-5.

(b) 5-Chloromethyl-2,4-dichloropyridine 20.2 g. of 2,4-dichloropyridin-5-methanol (0.11 mol.) and 150 ml. of phosphorus oxychloride are refluxed for 19 hours. Then the excess phosphorus oxychloride is removed in vacuo and ice is added to the residue. 5-Chloromethyl-2,4-dichloropyridine is filtered off, washed with water, dried in the desiccator over P2 O5 and recrystallized from hexane; yield 17.95 g. (83%), m.p. 55-56.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 73998-95-5, (4,6-Dichloropyridin-3-yl)methanol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; E. R. Squibb & Sons, Inc.; US4191831; (1980); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 146679-66-5, 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.146679-66-5, name is 3-Bromo-4-pyridinemethanol, molecular formula is C6H6BrNO, molecular weight is 188.02, as common compound, the synthetic route is as follows.

Step 2 ;To a mixture of (3-bromopyridin-4-yl)methanol (150 mg, 0.8 mmol, 1 eq.), 1-isopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (226 mg, 0.96 mmol, 1.2 eq.), Pd(dppf)Cl2 (58 mg, 0.08 mmol, 0.1 eq.), and K2CO3 (331 mg, 3.0 mmol, 3 eq.) in a RB flask were added dioxane (6 mL) and water (2 mL). The mixture was heated at 100 C. for 2 h, cooled, filtered, and concentrated. The crude was purified on silica gel using a mixture of EtOAc and hexanes as eluent to give (3-(1-isopropyl-1H-pyrazol-5-yl)pyridin-4-yl)methanol (75 mg, 43%) as a yellow oil. LRMS (M+H+) m/z 218.1.

Statistics shows that 146679-66-5 is playing an increasingly important role. we look forward to future research findings about 3-Bromo-4-pyridinemethanol.

Reference:
Patent; Global Blood Therapeutics, Inc.; The Regents of the University of Califorina; Cytokinetics, Inc.; Metcalf, Brian; Chuang, Chihyuan; Warrington, Jeffrey; Paulvannan, Kumar; Jacobson, Matthew P.; Hua, Lan; Morgan, Bradley; US2015/344483; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 19539-50-5 ,Some common heterocyclic compound, 19539-50-5, molecular formula is C7H5NO, 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 solution of 198.2 (3.82g, 32.07mmol, l .Oeq) in methanol (300mL), 10% palladium on charcoal (7.0g) was added. Hydrogen was purged through reaction mixture for 2-3h. After completion of reaction, reaction mixture was filtered through celite-bed and washed with ethanol. Filtrate was concentrated under reduced pressure to obtain198.3 (3.5g, 90.11%). MS(ES): m/z 122.14 [M+H]+

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 19539-50-5, Furo[2,3-c]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NIMBUS LAKSHMI, INC.; GREENWOOD, Jeremy Robert; HARRIMAN, Geraldine C.; LEIT DE MORADEI, Silvana Marcel; MASSE, Craig E.; MCLEAN, Thomas H.; MONDAL, Sayan; (401 pag.)WO2018/71794; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 5345-47-1 ,Some common heterocyclic compound, 5345-47-1, molecular formula is C6H6N2O2, 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.

2-Amino-nicotinic acid (10.0g, 72.4mmol) was dissolved in a mixed solution of methanol (200mL) and sulfuric acid (10mL), and the solution was stirred under reflux for 35 hours. A saturated aqueous solution of sodium bicarbonate was added to the reaction solution at 0C, which was extracted with ethyl acetate, the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo, the residue was purified by NH silica gel column chromatography to obtain the title compound (5.26g, 34.6mmol, 48%) as a white solid. 1H-NMR Spectrum (CDCl3) delta(ppm) : 3.89 (3H, s), 6.63 (1H, ddd, J=1.1, 4.8, 7.7Hz), 8.13 (1 H, dd, J=1.6, 7.7Hz), 8.22 (1 H, dd, J=1.8, 4.8Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5345-47-1, its application will become more common.

Reference:
Patent; Eisai Co., Ltd.; EP1669348; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 63071-13-6, 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.63071-13-6, name is 4-Chloropicolinaldehyde, molecular formula is C6H4ClNO, molecular weight is 141.56, as common compound, the synthetic route is as follows.

A mixture of A-i (1.5 g, 10.6 mmol) and 4-methylbenzene- sulfonohydrazide (1.97 g, 10.6 mmol) in methanol (15 mL) was stirred at 20C for 3 hours.The solid was collected by filtration, washed with MeOH (3 mL), and dried in oven to afford A-2 (2400 mg, 7.75 mmol) as a solid. ?H NMR (400MHz, DMSO-d6) oH = 11.96 (s, 1H), 8.53 (d, 1H), 7.90 (s, 1H), 7.78 (d, 2H), 7.71 (d, JH), 7.53 (dd, IH), 7.43 (d, 2H), 2.37 (s, 3H).

The chemical industry reduces the impact on the environment during synthesis 63071-13-6, I believe this compound will play a more active role in future production and life.

Reference:
Patent; PRAXIS PRECISION MEDICINES, INC.; REDDY, Kiran; MARTINEZ BOTELLA, Gabriel; GRIFFIN, Andrew, Mark; MARRON, Brian, Edward; (120 pag.)WO2019/35951; (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. 142266-62-4, name is 2,5,6-Trichloronicotinamide. A new synthetic method of this compound is introduced below., Quality Control of 2,5,6-Trichloronicotinamide

To a mixture of 2,5,6-trichloronicotinamide (Intermediate P; 1.4 g, 6.1 mmol) in THF (12 mL) was added oxalyl chloride, 2 M solution in DCM (3.3 mL, 6.5 mmol) at rt and the mixture was stirred and heated at 65 C. for 3 h. The mixture was cooled to 0 C. To the cooled mixture was added a solution of 1,4-diisopropyl-1H-pyrazol-5-amine (Intermediate 161; 1.03 g, 6.13 mmol) in THF (5 mL) and the mixture was stirred at rt for 15 h. The reaction mixture was quenched with satd NaHCO3 (100 mL), extracted with EtOAc (2*50 mL), washed with brine (1*50 mL), dried over Na2SO4, filtered, and concentrated in vacuo. The crude material was purified by silica gel chromatography (eluent: 0-50% EtOAc-EtOH (3:1)/heptane) to provide 2,5,6-trichloro-N-((1,4-diisopropyl-1H-pyrazol-5-yl)carbamoyl)nicotinamide (2.43 g, 5.79 mmol, 94% yield) as orange syrup. 1H NMR (400 MHz, DMSO-d6) delta 11.36 (br s, 1H), 9.39 (br s, 1H), 8.63 (s, 1H), 7.33 (s, 1H), 4.37 (dt, J=13.3, 6.6 Hz, 1H), 2.64-2.75 (m, 1H), 1.33 (d, J=6.4 Hz, 6H), 1.13 (d, J=7.0 Hz, 6H), m/z (ESI, +ve ion): 417.6 (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, 142266-62-4, 2,5,6-Trichloronicotinamide.

Reference:
Patent; Amgen Inc.; ALLEN, John Gordon; LANMAN, Brian Alan; CHEN, Jian; REED, Anthony B.; CEE, Victor J.; LIU, Longbin; LOPEZ, Patricia; WURZ, Ryan Paul; NGUYEN, Thomas T.; Booker, Shon; ALLEN, Jennifer Rebecca; CHU-MOYER, Margaret; AMEGADZIE, Albert; CHEN, Ning; GOODMAN, Clifford; LOW, Jonathan D.; MA, Vu Van; MINATTI, Ana Elena; NISHIMURA, Nobuko; PICKRELL, Alexander J.; WANG, Hui-Ling; SHIN, Youngsook; SIEGMUND, Aaron C.; YANG, Kevin C.; TAMAYO, Nuria A.; WALTON, Mary; XUE, Qiufen; US2019/374542; (2019); 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. 5315-25-3, name is 2-Bromo-6-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows. name: 2-Bromo-6-methylpyridine

Preparative Example 65 (0977) (0978) Step A (0979) To a stirred solution of n-butyllithium (1 L, 1.6 M in hexane) in tetrahydrofuran was added diisopropylamine (600 mL) dropwise through a dropping funnel at -10 C. under an N2 atmosphere for 30 minutes. The ice bath was removed and the reaction mixture was cooled to -78 C. A solution of 2-bromo-6-methyl pyridine (100 g, 0.58 mol) in THF (1.6 L) was added and the color changed pale yellow to dark brown. The mixture was stirred for 1 hour at the same temperature and then N,N?-dimethylformamide (200 mL, 2.147 mol) was added. After 60 minutes at -78 C., methanol (1.6 L) and acetic acid (160 mL, 2.49 mol) were added. Then sodium borohydride (28 g, 0.557 mol) was added at -78 C. and the mixture was allowed to come to room temperature and was stirred overnight. The color changed dark brown to yellow color. The reaction mixture was diluted with ethyl acetate (3.0 L) and 10% citric acid solution (1.5 L) and was extracted with EtOAc (2×2 L), and washed with brine (1 L). The combined organic extracts were dried over Na2SO4 and solvents were removed under reduced pressure. The residue was purified by column chromatography on silica gel (60-120 mesh) using ethyl acetate/n-heptane (30/70) to afford the title compound as a pale yellow oil (90 g, 76.5%). (0980) 1H-NMR (400 MHz, CDCl3): delta=7.43 (t, 1H), 7.34 (d, 1H), 7.16 (d, 1H), 4.02 (q, 2H), 3.09 (t, 1H), 3.01 (t, 2H)

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, 5315-25-3, 2-Bromo-6-methylpyridine.

Reference:
Patent; AC IMMUNE SA; PIRAMAL IMAGING SA; KROTH, Heiko; NAMPALLY, Sreenivasachary; MOLETTE, Jerome; GABELLIERI, Emanuele; BENDERITTER, Pascal Andre Rene; FROESTL, Wolfgang; SCHIEFERSTEIN, Hanno; MUELLER, Andre; SCHMITT-WILLICH, Heribert; BERNDT, Mathias; (228 pag.)US2017/2005; (2017); 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. 1065267-14-2, name is (3,5-Difluoropyridin-2-yl)methanol. This compound has unique chemical properties. The synthetic route is as follows. name: (3,5-Difluoropyridin-2-yl)methanol

[Step 2] Production of 4-chloro-2-[(3,5-difluoropyridin-2-yl)methoxy]-6,7-dihydro-5H-cyclopenta[b]pyridine To 2,4-dichloro-6,7-dihydro-5H-cyclopenta[b]pyridine 1-oxide (200 mg) and (3,5-difluoropyridin-2-yl)methanol(185 mg) was added THF (8 mL) and then added NaH (60% dispersion in oil, 59 mg) under ice water cooling, then the mixture was stirred at room temperature for 3 hours. After that phosphorus trichloride (175 mg) was added to the mixture under ice water cooling, and the mixture was stirred for 30 minutes. The reaction mixture was added with aqueous sodium bicarbonate solution, water and ethyl acetate, and subjected to extraction. The organic layer was dried over anhydrous sodium sulfate, filtered off, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give the title compound (63 mg) as a white powder.

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, 1065267-14-2, (3,5-Difluoropyridin-2-yl)methanol.

Reference:
Patent; Nippon Shinyaku Co., Ltd.; TSUJI, Takashi; SHIRAI, Masaaki; EP2891656; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem