Day: June 22, 2021

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

Adding a certain compound to certain chemical reactions, such as: 885588-12-5, 2-Bromo-5-fluoro-4-pyridinecarboxylic acid, 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, 885588-12-5, blongs to pyridine-derivatives compound. Application In Synthesis of 2-Bromo-5-fluoro-4-pyridinecarboxylic acid

To a cooled solution of 2-bromo-5-fluoroisonicotinic acid (3.0 g, 13.6 mmol) in benzene (20 ml) and methanol (10 ml) is dropwise over a period of 15 min added under stirring and cooling (trimethylsiliyl)diazomethane (2 M in ether, 14 ml, 28 mmol). The yellow solution is stirred for 1.5 h without cooling and evaporated to dryness. Purification of the residue (3.3 g) bychromatography on a 50 g Silicycle silica cartridge using a heptane / ethyl acetate 10-50% gradient affords methyl 2-bromo-5-fluoroisonicotinate (2.82 g, 88.4%) as a light yellow solid, mp.: 43 – 6C. MS: m/z= 233.9 (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,885588-12-5, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; FLOHR, Alexander; GOBBI, Luca; GROEBKE ZBINDEN, Katrin; KOERNER, Matthias; PETERS, Jens-Uwe; WO2012/76430; (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. 33252-63-0, name is 5-(Trifluoromethyl)pyridin-2-ol. A new synthetic method of this compound is introduced below., Safety of 5-(Trifluoromethyl)pyridin-2-ol

V-bromosuccinimide (NBS, 39.0Og, 0.22 mol) is added portionwise to a solution of 5- {trifluoromethyl)pyridin-2-ol (30.0Og, 0.18 mol) in DMF (180 ml_), and the resulting mixture is stirred for 2 hours. The mixture is poured into water (1200 ml.) and the precipitate is collected by filtration. The crystal is dried in vacuo to give the product as a white solid (1st crystal : 28.1Og). The filtrate is extracted with EtOAc, and the organic layer is concentrated. The residue is poured into water and the precipitate is collected by filtration. The crystal is dried in vacuo to give 3-bromo-5-(trifluoromethyl)pyridin-2-ol as a yellow solid. 1H-NMR (400MHz, CDCI3), delta (ppm): 7.86 (d, 1 H), 8.02 (d, 1 H), 13.17 (br, 1 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, 33252-63-0, 5-(Trifluoromethyl)pyridin-2-ol.

Reference:
Patent; NOVARTIS AG; WO2008/58961; (2008); 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. 66572-56-3, name is 2-Bromoisonicotinic acid, molecular formula is C6H4BrNO2, 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. Recommanded Product: 66572-56-3

To a solution of 2-bromoisonicotinic acid (1.87 g, 9.26 mmol), 1H-imidazole (573mg, 8.42 mmol) and Cs2C03 (6.03 g, 18.5 mmol) in DMSO (18.6 mL), was added Cui (176mg, 0.926 mmol). The mixture was heated to 125C, stirred for 18 hours, cooled to room10 temperature, filtered and purified by preparative HPLC (1 0-90% acetonitrile in water) to givethe title compound as a light pink solid (1. 72 g, 98% ). MS 190 (MH+).

With the rapid development of chemical substances, we look forward to future research findings about 66572-56-3.

Reference:
Patent; SENOMYX, INC.; TACHDJIAN, Catherine; KARANEWSKY, Donald; WERNER, Sara; DARMOHUSODO, Vincent; YAMAMOTO, Jeff; WO2014/25706; (2014); 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 170850-45-0, name is 6-(p-Tolyl)pyridin-3-amine. This compound has unique chemical properties. The synthetic route is as follows. category: pyridine-derivatives

General procedure: 4.4.1 N-(4′-Methylbiphenyl-4-yl)acetamide 6b. Compound 4a (0.33 mmol, 60 mg), 5b (0.70 mmol, 1.104 g mL-1, 50 muL), PS-NMM (0.70 mmol, 175 mg) and CH2Cl2 (10 mL) were stirred at rt for 48 h. The mixture was filtered and the filtrate was concentrated under reduced pressure. The crude product was purified by chromatography on silica gel, CH2Cl2/EtOAc 9:1, to give 77 mg of the pure expected product as an off-white solid (99% yield).

With the rapid development of chemical substances, we look forward to future research findings about 170850-45-0.

Reference:
Article; Baltus, Christine B.; Press, Neil J.; Antonijevic, Milan D.; Tizzard, Graham J.; Coles, Simon J.; Spencer, John; Tetrahedron; vol. 68; 45; (2012); p. 9272 – 9277;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 17228-69-2, 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. 17228-69-2, name is 2-Chloro-4-methoxypyridine. A new synthetic method of this compound is introduced below.

General procedure: To a round bottle flask containing 1 (2 mmol) was added methyl iodide (10 mmol; 5 equiv.) and the mixture was stirred at room temperature or refluxed overnight. The reaction was monitored by TLC. After completion, the resulting precipitate was separated by filtration and purified by recrystallization.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,17228-69-2, its application will become more common.

Reference:
Article; Yi, Xiao; Chen, Jing; Xu, Xiuling; Ma, Yongmin; Synthetic Communications; vol. 47; 9; (2017); p. 872 – 877;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 52200-48-3, 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 52200-48-3 as follows.

Intermediate [Example Int22.13-bromo-2-ethoxypyridine3-Bromo-2-chloropyridine (10.0 g) was dissolved in ethanol (100 mL) and a solution of sodium ethylate in ethanol (70.8 mL, 21 %) was added. The mixture was heated to reflux overnight. The solvent was then removed in vacuo and the residue was dissolved in ethyl acetate and washed with satd. aqueous ammonium chloride solution. The organic layer was dried over sodium sulphate, and the solvent was evaporated. The crude product was purified by column chromatography on silica gel (eluent: cyclohexane / ethyl acetate 10: 1 ) to yield 7.26 g (69%) of an yellow oil.1 H-NMR (400MHz, DMSO-d6): delta [ppm]= 1 .34 (t, 3H), 4.37 (q, 2H), 6.93 (dd, 1 H), 8.02 (dd, 1 H), 8.15 (dd, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,52200-48-3, its application will become more common.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; KOPPITZ, Marcus; SCHULZE, Volker; KOSEMUND, Dirk; SCHIROK, Hartmut; BADER, Benjamin; LIENAU, Philipp; MARQUARDT, Tobias; WEGSCHEIDT-GERLACH, Christof; SIEMEISTER, Gerhard; PRECHTL, Stefan; WENGNER, Antje; BOeMER, Ulf; WO2011/64328; (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 113118-81-3, name is 5-Bromonicotinaldehyde. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C6H4BrNO

General procedure: To a solution of the proper bromopyridine-carbaldehyde (VI, 1 eq.) in MeOH, NaBH4 (2 eq.) was added portionwise. The mixture was stirred at room temperature for 3 hours. After this time, water was added and the mixture was concentrated under vacuum. The residue was diluted with water and extracted with DCM. The combined organic phases were dried over anhydrous MgS04, filtered and evaporated under reduced pressure to give the intermediate compound having general formula VII, which was used in the next step without further purification. (0151) (5-Bromopyridin-3-yl)methanol (Vila). The title compound was obtained according to general procedure B, step 1 using 5-bromopyridine-3-carbaldehyde (Via, 0.25 g, 1.34 mmol), NaBH4 (0.10 g, 2.69 mmol). The crude (0.15 g) was used in the next step without further purification. Yield = 60%.

With the rapid development of chemical substances, we look forward to future research findings about 113118-81-3.

Reference:
Patent; AZIENDE CHIMICHE RIUNITE ANGELINI FRANCESCO – A.C.R.A.F. S.P.A.; FURLOTTI, Guido; CAVARISCHIA, Claudia; BUONFIGLIO, Rosa; OMBRATO, Rosella; IACOANGELI, Tommaso; (61 pag.)WO2019/215075; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem