Tag: M.W=200-300

These common heterocyclic compound, 349-60-0, name is 1-Methoxy-3,5-bis(trifluoromethyl)benzene, 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. HPLC of Formula: C9H6F6O

3,5-Bis(trifluoromethyl)anisole (5.0 g 21 mmol) and TMEDA (4.0 mL, 3.0 g,26 mmol) were dissolved in dry Et2O (60 mL), cooled to -10 0C and treated in portions with H-BuLi (2.5 M in hexanes; 10 mL, 25 mmol). The mixture was warmed to 25 0C and stirred for 90 min. The mixture was cooled to -78 0C, treated dropwise with DMF (2.3 mL, 2.2 g, 30 mmol), stirred for 30 min, warmed to 25 0C and stirred for 30 min. The reaction was quenched by addition of H2O (50 mL) and extracted with Et2O (2 x 75 mL). The combined organic fractions were washed with satd NaCl solution (30 mL), dried (Na2SO4) and evaporated. The residue was purified by silica gel chromatography to give the anisaldehyde derivative (3.3 g). This material (3.0 g, 11 mmol) was dissolved in CH2Cl2 (75 mL), cooled to -78 0C and treated with BBr3 (1 M solution in CH2Cl2; 12 mL, 12 mmol). The mixture was stirred for 30 min at -78 0C, warmed to 25 0C and stirred for 90 min. H2O (100 mL) was added and stirring was continued for 30 min. The separated organic phase was washed with satd NaCl solution, dried (Na2SO4) and evaporated. The residue was purified by silica gel chromatography with 0-20percent EtOAc/hexane to give the purified aldehyde (2.0 g): 1H NMR (400 MHz, CDCl3) delta 12.27 (s, IH), 10.34 (s,lH), 7.51 (s, IH); EIMS m/z 258.

The synthetic route of 1-Methoxy-3,5-bis(trifluoromethyl)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DOW AGROSCIENCES LLC; YOUNG, David; SHABER, Steven; AVILA-ADAME, Cruz; BREAUX, Nneka; RUIZ, James; SIDDALL, Thomas; WEBSTER, Jeffery; WO2010/83307; (2010); A2;,
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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. 1236000-51-3, name is N-Methyl-1-(4-(trifluoromethoxy)phenyl)methanamine hydrochloride, A new synthetic method of this compound is introduced below., HPLC of Formula: C9H11ClF3NO

Intermediate 26 {[5-(4-bromophenyl)-2-thienyl]methyl}methyl({4[(trifluoromethyl)oxy]phenyl}methyl)amine (1-[5-(4-bromophenyl)-2-thienyl]-N-methyI-N-({4-[(trifluoromethyl)oxy]phenyl}methyl)methanamine). To a solution of 0.3 g of Intermediate 25 and 0.26 g of Intermediate 1 in 8.5 ml of DCE under N2 atmosphere were added dropwise 0.226 ml of Et3N and 0.342 g of NaHB(AcO)3 consecutively. The mixture was stirred overnight at room temperature and 1 N NaOH was added. The resulting mixture was extracted with CH2CI2, the combined organic layers were dried over Na2SO4, filtered and concentrated to dryness. The crude was purified by chromatography on silica gel eluting with EtOAc-Hex 0:100 to 10:90 to afford 0.383 g of the desired compound with 10% of the starting aldehyde. This mixture was re-purified on silica gel eluting with EtOAc-Hex 0:100 to 10:90 to afford 0.348 g (67%) of the title compound as a colourless oil.1H NMR (delta, ppm, CDCI3): 7.47 (dd, 4H); 7.42 (d, 2H); 7.18 (d, 2H); 7.15 (d, 1 H); 6.90 (d, 1 H); 3.75 (s, 2H); 3.58 (s, 2H); 2.28 (s, 3H). [ES MS] m/z: 456 (MH+).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; GLAXO GROUP LIMITED; BUENO-CALDERON, Jose Maria; FERNANDEZ-MOLINA, Jorge; LEON-DIAZ, Maria Luisa; MALLO-RUBIO, Araceli; MANZANO-CHINCHON, M Pilar; WO2010/81904; (2010); A1;,
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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. 239122-51-1, name is 5-Bromo-3-fluoro-2-methoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 239122-51-1

Preparation of 3-amino-5-fluoro-4-methoxybenzonitrile[00165] A mixture of 5-bromo-3-fluoro-2-methoxyaniline (500 mg, 2.27 mmol), potassium ferrocyanide (II) hydrate (240 mg, 0.57 mmol), sodium carbonate (241 mg, 2.27 mmol) and palladium(II) acetate (25.5 mg, 0.11 mmol) in DMA (2 mL) was purged with nitrogen and heated at 120 0C for 6 hours. The reaction mixture was diluted with ethyl acetate (20 mL) and filtered through CELITE. The filtrate was washed with water (20 mL), 5% NH4OH (10 mL), dried over MgSO4, filtered and concentrated to isolate Intermediate 25 (213 mg, 56.4 % yield). HPLC: Rt = 0.73 min. (PHENOMENEX Luna 5 micron C18 4.6 x 30 mm, 10-90% aqueous methanol containing 0.1% TFA, 2 min. gradient, flow rate = 5 mL/min., detection at 254 nm). MS (ES): m/z = 167.2 [M+H]+. Intermediate 25 was used in the synthesis of Examples 234 and 239.

The synthetic route of 239122-51-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; FINK, Brian; CHEN, Libing; GAVAI, Ashvinikumar; HE, Liqi; KIM, Soong-Hoon; NATION, Andrew; ZHAO, Yufen; ZHANG, Litai; WO2010/42699; (2010); A1;,
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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 202865-58-5 as follows. category: ethers-buliding-blocks

Intermediate Example Int 10.22.011 -bromo-5-f luoro-2-methoxy-4-(methy Isu Ifany l)benzeneTo a stirred solution of sodium methanethiolate (0.47 g) in DMF (15 mL) at 0 C was added 1 -bromo-4,5-difluoro-2-methoxybenzene (1 .5 g). The mixture was stirred at r.t. for 2 h. Water was added and the mixture was extracted with ethyl acetate. The organic phase was washed with saturated sodium chloride solution, dried (sodium sulfate) and the solvent was removed in vacuum. Silica gel chromatography gave 1 .46 g of the title compound.

According to the analysis of related databases, 202865-58-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; SCHULZE, Volker; KOSEMUND, Dirk; WENGNER, Antje, Margret; SIEMEISTER, Gerhard; STOeCKIGT, Detlef; LIENAU, Philip; SCHIROK, Hartmut; BRIEM, Hans; WO2012/143329; (2012); A1;,
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Adding a certain compound to certain chemical reactions, such as: 887267-47-2, name is 2-Bromo-5-(trifluoromethoxy)aniline, belongs to ethers-buliding-blocks compound, 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 887267-47-2, Computed Properties of C7H5BrF3NO

General procedure: Triphosgene (0.14 g, 0.48 mmol) was dissolved in anhydrous CH2Cl2 (15 mL) and the mixture was stirred on the ice-bath for 15 min. 3-Bromo-5-(trifluoromethyl)aniline (0.3 g, 1.2 mmol) in anhydrous CH2Cl2 (10 mL) was added dropwise to the above mixture and stirring continued for 20 min. Et3N (0.2 mL, 1.44 mmol) diluted with CH2Cl2 (5 mL) was then added into the mixture. Stirring was continued for 20 min and a solution of Et3N (0.2 mL, 1.44 mmol), 4-pyridin-3-ylaniline (5) (0.2 g, 1.2 mmol) in anhydrous CH2Cl2 (20 mL) was added. After completion of the action, the reaction was quenched with dilute Na2CO3. The organic layer was washed with water and brine, and dried over Na2SO4. After filtration and concentration in vacuo, the residues was purified by silica gel flash chromatography (PE/AcOEt = 6:1) yielding (L1). yield 73%

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.

Reference:
Article; Su, Ping; Wang, Jinfeng; Shi, Yaling; Pan, Xiaoyan; Shao, Ruili; Zhang, Jie; Bioorganic and Medicinal Chemistry; vol. 23; 13; (2015); p. 3228 – 3236;,
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Some common heterocyclic compound, 92028-21-2, name is 6-Methoxy-[1,1′-biphenyl]-3-amine hydrochloride, molecular formula is C13H14ClNO, 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. HPLC of Formula: C13H14ClNO

To a flask containing 3.91 g (10 mmol) of compound B (Example 13, part b), 3.06 g (13 mmol) of 4-methoxy-3-phenylaniline hydrochloride (from TCI), 0.46 g (0.5 mmol) of tris(dibenzylidineacetone)dipalladium(0), 0.93 g (1.5 mmol) of racemic-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl, and 2.21 g (23 mmol) of sodium tert-butoxide was added 50 mL of toluene, and the mixture was heated at 95 C. for 5.5 hours under an nitrogen atmosphere. The mixture was partitioned between 1.0 M aqueous NaHSO4 and diethyl ether, and the phases were separated. The diethyl ether phase was diluted with one volume of hexanes, and was washed once each with 1.0 M aqueous NaHSO4 and brine, dried over Na2SO4, filtered, and concentrated to a dark oil. The oil was purified by silica gel chromatography, using 12% EtOAc/88% hexanes as eluent, to give compound D as a yellow foam. 1H NMR (300 MHz, DMSO-d6) delta 7.76 (s, 1H), 7.38-7.13 (m, 10H), 6.95-6.81 (m, 7H), 4.28 (s, 2H), 3.61 (s, 3H), 3.16 (m, 2H), 2.53 (m, 2H), 1.29 (s, 9H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 92028-21-2, its application will become more common.

Reference:
Patent; Moran, Edmund J.; Jacobsen, John R.; Leadbetter, Michael R.; Nodwell, Matthew B.; Trapp, Sean G.; Aggen, James; Church, Timothy J.; US2003/229058; (2003); A1;,
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Synthetic Route of 887267-47-2, These common heterocyclic compound, 887267-47-2, name is 2-Bromo-5-(trifluoromethoxy)aniline, 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: 1,1-Cyclopropanedicarboxylic acid (5) (12.0 g, 15.4 mmol) was dissolved in anhydrous THF (50 mL). Then triethanolamine (2.0 mL,13.9 mmol) was added to the mixture and the mixture was stirred on the ice-bath for 30 min. SOCl2 (1.2 mL, 16.66 mmol) was then added. Stirring was continued for 2h, a solution of 3,5-dimethylaniline 6 (3.6 g, 15.4 mmol) in anhydrous THF (10 mL) was added and continued stirring for 2h, after that, the ice bath was removed, and the mixture was stirred at room temperature overnight. After the completion of the reaction, the mixture was filtered and concentrated in vacuo. The residues was purified by silica gel flash chromatography (PE/AcOEt = 5:1) to yield 7 as white solid (0.8 g, 30.7%).

Statistics shows that 2-Bromo-5-(trifluoromethoxy)aniline is playing an increasingly important role. we look forward to future research findings about 887267-47-2.

Reference:
Article; Li, Chuansheng; Shan, Yuanyuan; Sun, Ying; Si, Ru; Liang, Liyuan; Pan, Xiaoyan; Wang, Binghe; Zhang, Jie; European Journal of Medicinal Chemistry; vol. 141; (2017); p. 506 – 518;,
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Electric Literature of 38603-09-7, These common heterocyclic compound, 38603-09-7, name is 1,3-dibromo-2-methoxybenzene, 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-(3,5-Dibromo-4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (B) A mixture of 1,3-dibromo-2-methoxybenzene (0.6586 g, 2.48 mmol), bis(pinacolato)diboron (0.4402, 1.73 mmol) and 4,4′-di-tert-butyl-2,2′-dipyridyl (1.3 mg, 0.0048 mmol) in degassed anhydrous THF (2.5 mL) in a reaction tube was purged by bubbling nitrogen through for 5 min. Di-mu-methoxybis(1,5-cyclooctadiene)diiridium(I) (1.6 mg, 0.0024 mmol) was added and the mixture was purged with nitrogen for a few more minutes. The tube was then capped and heated at 80 C. for 19 h. More di-mu-methoxybis(1,5-cyclooctadiene)diiridium(I) (3.4 mg, 0.0051 mmol) and 4,4′-di-tert-butyl-2,2′-dipyridyl (2.9 mg, 0.0108 mmol) was added and the mixture was purged with nitrogen again. The tube was then capped and heated at 80 C. for a further 18 h. The solvent was evaporated and the residue was purified by flash chromatography (silica gel, 5% EtOAc/pet. ether) to afford 0.8575 g (88%) of the title compound as a white solid. 1H NMR delta (ppm)(CDCl3): 1.33 (12H, s), 3.90 (3H, s), 7.92 (2H, s).

Statistics shows that 1,3-dibromo-2-methoxybenzene is playing an increasingly important role. we look forward to future research findings about 38603-09-7.

Reference:
Patent; Institute for OneWorld Health; US2009/270398; (2009); A1;,
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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. 887267-47-2, name is 2-Bromo-5-(trifluoromethoxy)aniline, A new synthetic method of this compound is introduced below., Recommanded Product: 2-Bromo-5-(trifluoromethoxy)aniline

To a solution of 2-bromo-5-(trifluoromethoxy)aniline (7 g, 27.34 mmol), ethyl acrylate (4.4mL, 40.95 mmol) and triethylamine (7.6 mL, 54.68 mmol) in MeCN (70 mL) was addedpalladium(1I) acetate (614 mg, 2.73 mmol) and tris(2-methylphenyl)phosphine (2.24 g, 8.2 mmol). The mixture was heated to 120 C for 12 h under a nitrogen atmosphere. After cooling the reaction to room temperature, the mixture was concentrated in vacuo. The crude residue was purified by silica gel chromatography (petroleum ether EtOAc = 100 : 1 to 50ito 20: 1) to give the title compound (2.8 g, 29%) as a yellow oil.

The synthetic route of 887267-47-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; ROMERO, F. Anthony; MAGNUSON, Steven; PASTOR, Richard; TSUI, Vickie Hsiao-Wei; MURRAY, Jeremy; CRAWFORD, Terry; ALBRECHT, Brian, K.; COTE, Alexandre; TAYLOR, Alexander, M.; LAI, Kwong Wah; CHEN, Kevin, X.; BRONNER, Sarah; ADLER, Marc; EGEN, Jackson; LIAO, Jiangpeng; WANG, Fei; CYR, Patrick; ZHU, Bing-Yan; KAUDER, Steven; (0 pag.)WO2016/86200; (2016); A1;,
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Application of 6052-10-4, 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. 6052-10-4 name is 4,4′-(Ethane-1,2-diylbis(oxy))dianiline, This 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.

The reatcion of 4-(4-hexyloxybenzoyloxy) benzaldehyde (22 mmol) in anhydrous EtOH(50 mL) with [1,2-bis(4-aminophenoxy)ethane (11 mmol) in the presence of PTSA[3, 21, 22]. The reaction mixture was stirred for 16 hr at the room temperature. Thecrude precipitate was collected by filtration and purified by the recrystallization of bothchloroform and ethyl acetate solvents. The prepared HBPE-1 was confirmed by 1H-NMR. 1H-NMR (CDCl3, ppm): delta 0.94-0.85 (t, 6H, -CH3), 1.50-1.24 (m, 12H, -(CH2)3-), 1.84-1.79(m, 4H, -CH2CH2O-), 4.07-4.02 (t, 4H, -CH2CH2O-), 4.37 (s, 4H, -OCH2-), 7.02-6.96 (t,8H, Ar-H), 7.33-7.24 (d, 8H, Ar-H), 7.97-7.94 (d, 4H, Ar-H), 8.16-8.13 (d, 4H, Ar-H), 8.49(s, 2H, -CH = N).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4,4′-(Ethane-1,2-diylbis(oxy))dianiline, and friends who are interested can also refer to it.

Reference:
Article; Park, Joo Hoon; Singu, Bal Sydulu; Choi, Ok Byung; Lee, Hwan Myung; Lee, Jin Young; Kim, Sung Jo; Cha, Eun Hee; Park, Seon Nam; Kwak, Myeong Heon; So, Bong Keun; Kim, Ran Hee; Lee, Soo Min; Yoon, Kuk Ro; Molecular Crystals and Liquid Crystals; vol. 650; 1; (2017); p. 1 – 6;,
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