Author: Jessica.F

Application of 578-57-4, These common heterocyclic compound, 578-57-4, name is 1-Bromo-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.

General procedure: A 10 mL vial was charged with CuI (9.5 mg, 0.05 mmol), PSAP (30 mg,0.05 mmol, > 100 mesh), K3PO4 (424 mg, 2 mmol), aryl bromides (1mmol), amines (1.5 mmol), DEG (2 mL), and a magnetic stir bar. The vessel was sealed with a septum and placed into a preheated oil batchat 70 C. The reaction mixture was held at this temperature for 14 hours. After cooling to r.t., the reaction mixture was filtered, and the precipitates were thoroughly washed with water and EtOAc (3 × 20mL). The combined organic phases were washed with water and brine, dried over anhydrous Na2SO4, and concentrated in vacuo. Theresidue was purified using flash column chromatography on silica gel(eluting with petroleum ether/EtOAc) to afford the desired products.

Statistics shows that 1-Bromo-2-methoxybenzene is playing an increasingly important role. we look forward to future research findings about 578-57-4.

Reference:
Article; Yi, Zhou; Huang, Manna; Wan, Yiqian; Zhu, Xinhai; Synthesis; vol. 50; 19; (2018); p. 3911 – 3920;,
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Related Products of 4342-46-5, These common heterocyclic compound, 4342-46-5, name is 4-Methoxycyclohexanamine, 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: To a solution of 7a-d (1.0 equiv.) and amine (2.0 equiv.) in dioxane was added glacial acetic acid (0.2 equiv.), then the mixture was stirred and heated at 110 C in a sealed tube for 10-20 h. The mixture was concentrated under vacuum, and the residue was purified by column chromatography on silica gel, using petroleum ether/ethyl acetate to afford target products 8-25.

The synthetic route of 4342-46-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Dongfeng; Liu, Yang; Zhang, Chunlin; Zhang, Hao; Wang, Bin; Xu, Jian; Fu, Lei; Yin, Dali; Cooper, Christopher B.; Ma, Zhenkun; Lu, Yu; Huang, Haihong; Molecules; vol. 19; 4; (2014); p. 4380 – 4394;,
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Synthetic Route of 20781-20-8, 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 20781-20-8 as follows.

To a solution of ethyl (4aS)-l-(4-fluorophenyl)-6-oxo-4,5,7,8-tetrahydrobenzo[f]indazole-4a- carboxylate (lg) (3.16 g, 8.92 mmol) and (2,4-dimethoxyphenyl)methanamine (2.68 mL, 17.8 mmol) in DCE (40 mL) was added acetic acid (1.54 mL, 26.8 mmol). After the reaction was stirred at rt for 5 min and cooled down in an ice-bath, sodium triacetoxyborohydride (5.l0g, 24.1 mmol) was added in portions. 5 Minute later, the reaction solution was allowed to warm to rt and continued stirring for 30 min. The solution was quenched (sat. aq. NaHCCE) and extracted (EtOAc). The organic layers were washed (brine), dried (Na2SC>4) and concentrated under reduced pressure. The crude product was purified by silica gel chromatography (0%-75% EtO Ac/hexanes, a gradient elution) to provide the title compound (4a) (4.15 g, 92% yield) as an off-white solid m/z (ESI, +ve ion) = 506.3 [M+H]+

According to the analysis of related databases, 20781-20-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ORIC PHARMACEUTICALS, INC.; DU, Xiaohui; EKSTEROWICZ, John; FANTIN, Valeria R.; REW, Yosup; SUN, Daqing; YE, Qiuping; ZHOU, Haiying; KAWAI, Hiroyuki; MOORE, Jared; PHAM, Johnny; WU, Kejia; ZHU, Liusheng; (116 pag.)WO2020/76999; (2020); 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. 37895-73-1, name is 1,2-Dibromo-4,5-dimethoxybenzene, A new synthetic method of this compound is introduced below., Application In Synthesis of 1,2-Dibromo-4,5-dimethoxybenzene

a) Preparation of 4′,5′-Dimethoxy-[1,1′:2′,1″-terphenyl]-4,4″-dicarbonitrile A flask containing 4,5-dibromoveratrole (407 mg, 1.375 mmol), 4-cyanophenylboronic acid (606 mg, 4.125 mmol), Pd(PPh3)4 (159 mg, 0.1375 mmol), and Na2CO3 (729 mg, 6.875 mmol) was degassed and dioxane (6 mL) and H2O (3 mL) were added. Reaction was refluxed at 102 C. overnight then cooled to RT and diluted with EtOAc. Solution was washed with saturated NaHCO3 solution followed by brine and organic layer was collected, dried over Na2SO4, and concentrated. Chromatography using ISCO max gradient 50% EtOAc/hexane yielded product as a light yellow solid (467 mg, quantitative); 1H NMR (400 MHz) (CDCl3) delta 7.46-7.44 (m, 4H), 7.14-7.12 (m, 4H), 6.83 (s, 2H), 3.89 (s, 6H); 13C NMR (100 MHz) (CDCl3) delta 149.4, 145.6, 132.0, 131.3, 130.6, 118.7, 113.5, 110.6, 56.2.

The synthetic route of 37895-73-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY; LaVoie, Edmond J.; Arnold, Eddy; Bauman, Joseph D.; Kerrigan, John E.; Parhi, Ajit K.; Das, Kalyan; Kelley, Cody; Patel, Dishaben V.; US2015/322022; (2015); A1;,
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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. 768-70-7, name is 3-Ethynylanisole, This compound has unique chemical properties. The synthetic route is as follows., category: ethers-buliding-blocks

General procedure: In an oven-dried Schlenk tube 2-iodophenol 6 (0.5 mmol), terminalalkyne 4 (0.5 mmol), PdO/MWCNT (5 mol%), K2CO3(1 mmol) and solvent (DMSO) (1.0 mL) were added. Theresulting reaction mixture was stirred at 120 C for 24 h. Theprogress of the reaction was monitored by TLC. After completionof reaction, the reaction mixture was allowed to coolto room temperature, then diluted with (10 mL) ethyl acetateand NH4Cl (10 mL) was added fallowed by extraction withethyl acetate. The organic layers were dried (Na2SO4) andconcentrated in vacuum. Purification of the residue by silicagel column chromatography using petroleum ether/ethylacetate as the eluent furnished the benzofuran 7.

According to the analysis of related databases, 768-70-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Lakshminarayana, Bhairi; Mahendar, Lodi; Chakraborty, Jhonti; Satyanarayana, Gedu; Subrahmanyam, Ch; Journal of Chemical Sciences; vol. 130; 5; (2018);,
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Adding a certain compound to certain chemical reactions, such as: 4344-55-2, name is 4-Butoxyaniline, 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 4344-55-2, name: 4-Butoxyaniline

Example 303-(4-Butoxyphenyl)-2-thioxo-1,2,3,7-tetrahydro-4H-pyrrolo[2,3-d]pyrimidin-4-one; Ethyl 2-isothiocyanato-1H-pyrrol-3-carboxylate (400 mg) obtained by the method of Reference Example 36, or a method pursuant to thereto, and 4-butoxyaniline (330 mg) obtained by the method of Reference Example 12, or a method pursuant to thereto, were added to acetonitrile (5 ml). The resulting mixture was stirred for 4 hours at 70 C., and then was concentrated under reduced pressure, to obtain a crude solid. This crude solid was added to a solution of potassium tert-butoxide (440 mg) in ethanol (5 ml), and the resulting mixture was stirred for 24 hours at room temperature. Subsequently, 1 M hydrochloric acid was added thereto until the pH value reached 6. A solid precipitated therefrom was collected by filtration, washed with water and petroleum ether, and then dried under reduced pressure, and thus the title compound (254 mg) was obtained.MS(ESI+):316(M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Butoxyaniline, and friends who are interested can also refer to it.

Reference:
Patent; Suzuki, Hideo; Fujimoto, Takuya; Yamamoto, Takeshi; US2010/190747; (2010); A1;,
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Reference of 6943-97-1,Some common heterocyclic compound, 6943-97-1, name is 1-(3-Bromopropyl)-3-methoxybenzene, molecular formula is C10H13BrO, 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: A flask containing solution of Mg turnings (271 mg, 11.31 mmol) in THF (10 mL) and a few crystals of iodine under nitrogen was added a solution of compound 15 (2.42 g, 11.31 mmol) in THF (15 mL) drop wise and reflux for 3 hrs. After 3 hrs the majority of the Mg had dissolved and a clear grayish colored solution had formed. The solution was cooled to 0 C and a solution of compound 16 (1.5 g, 7.07 mmol) in THF was added drop wise. The mixture was allowed to warm slowly to rt and reaction was monitored by tlc. Once the starting material is consumed the reaction mixture was quenched by saturated aqueous NH4Cl solution (30 mL). The reaction mixture was extracted with EtOAc (20 mL x 3) and layer was separated and washed with brine and dried over MgSO4. Removal of solvent and drying under vacuum provided the crude product that was separated by flash chromatography.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-(3-Bromopropyl)-3-methoxybenzene, its application will become more common.

Reference:
Article; Asim, Muhammad; Klonowska, Daria; Choueiri, Christine; Korobkov, Ilia; Carlson, Kathryn E.; Katzenellenbogen, John A.; Durst, Tony; Bioorganic and Medicinal Chemistry Letters; vol. 22; 11; (2012); p. 3713 – 3717;,
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Electric Literature of 454-90-0, The chemical industry reduces the impact on the environment during synthesis 454-90-0, name is 3-(Trifluoromethyl)anisole, I believe this compound will play a more active role in future production and life.

A flame-dried 100 mL Schlenk tube was charged with bis(pinacolato)diboron (350 mg, 1.38 mmol), [Ir(COD)Cl]z (12 mg, 0.018 mmol), sodium methoxide (5 mg, 0.09 mmol), and 4,4′-di-tert-butyl-2,2′-dipyridyl (8 mg, 0.03 mmol). The flask was evacuated, placed under argon, and 3-trifluoromethylanisole (2.5 mL) was added. The flask was restoppered and evacuated (full vacuum, 2 minutes). The flask was sealed under vacuum and maintained at 90 C. (oil bath) for 96 h. Thereafter, the contents were transferred to a round bottom flask with the aid of ethyl acetate and purified by Kugelrohr distillation. The product, a viscous oil, distills at 120 C. 10 p.m. Isolated yield 497 mg (1.65 mmol, 60%). 1H NMR (400 MHz, CDCl3) delta 7.62 (s, 1H); 7.43 (s, 1H); 7.18 (s, 1H); 3.82 (s, 1H); 1.32 (s, 1H).

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, 3-(Trifluoromethyl)anisole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; The Regents of the University of California; Tanaka, Masahiro; Zhang, Chao; Shokat, Kevan M.; Burlingame, Alma L.; Hansen, Kirk; Bateman, Raynard L.; DiMagno, Stephen G.; (81 pag.)US2016/168151; (2016); A1;,
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Related Products of 1758-46-9,Some common heterocyclic compound, 1758-46-9, name is 2-Phenoxyethylamine, molecular formula is C8H11NO, 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.

c) (4-Methyl-3,4-dihydro-quinazolin-2-yl)-(2-phenoxy-ethyl)-amine hydroiodide 2-Phenoxyethylamine (26 mg, 0.19 mmol) was added to a solution of 4-methyl-2-methylsulfanyl-3,4-dihydro-quinazoline hydroiodide (50 mg, 0.16 mmol) in acetonitrile (1 ml), and the mixture was heated overnight (80° C.) in a screw-capped vial. The solvent was then evaporated and the mixture was suspended in diethyl ether. The title compound (52 mg, 62percent) was obtained from this mixture by filtration. MS: m/e=282.1 [M+H+]. 1H NMR (CDCl3): delta 1.40 (3H, d), 3.72 (2H, m), 4.14 (2H, m), 4.80 (2H, q), 6.94-7.07 (3H, m), 7.11-7.16 (2H, m), 7.26-7.34 (4H, m), 7.89 (1H, bs), 8.56 (1H, bs), 10.25 (1H, bs).

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

Reference:
Patent; Alanine, Alexander; Gobbi, Luca Claudio; Kolczewski, Sabine; Luebbers, Thomas; Peters, Jens-Uwe; Steward, Lucinda; US2006/252779; (2006); A1;,
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Synthetic Route of 17061-62-0, 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. 17061-62-0, name is Bis(4-methoxybenzyl)amine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

[0407j N,N-bis(4-methoxybenzyl)methanesulfonamide, Example 13.0. To a solution of bis(4-methoxybenzyl)amine 12.01 (100 g, 0.389 mol, 1 eq) in DCM (1 L) was added TEA (71 mL, 0.506 mol, 1.3 eq) followed by dropwise addition of methanesulfonyl chloride (36 mL, 0.46 mol, 1.2 eq). (The internal temperature was kept between 5-10 C during the addition of the methane sulfonyl chloride). Once the addition was complete, the cooling bath was removed. After 1.5 h, TLC showed complete loss of starting material. Water (1 L) was added to the reaction. The layers were separated and the aqueous layer was extracted with DCM (2x 500 mL). The combined organic layers were washed with brine (2x 1 L), dried over Na2SO4, and concentrated in vacuo. The material thus obtained was absorbed onto a plug of silica gel and purified by chromatography (silica gel (60-120 mesh) eluting with a gradient of 10-80% EtOAc in hexanes) to provide 120 g (0.36 mol, 92%) of the title compound Example 13.0 as white solid. ?H-NMR(400 MHz, CDC13) 7.26 (dd, J= 2.12, 6.60 Hz, 4H), 6.91 (dd, J= 2.12, 6.62 Hz, 4H), 4.28 (s, 4H), 3.83 (s, 6H), 2.75 (s, 3H). GC-MS (ESI p05. ion) mlz: = 335 (M+H).

The synthetic route of Bis(4-methoxybenzyl)amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; CHEN, Ning; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEIGNAN, Jeffrey; DRANSFIELD, Paul John; DU, Xiaohui; FU, Zice; HEATH, Julie Anne; HORNE, Daniel B.; HOUZE, Jonathan; KALLER, Matthew R.; KHAKOO, Aarif Yusuf; KOPECKY, David John; LAI, Su-Jen; MA, Zhihua; MCGEE, Lawrence R.; MEDINA, Julio C.; MIHALIC, Jeffrey T.; NISHIMURA, Nobuko; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; YANG, Kevin; YEH, Wen-Chen; DEBENEDETTO, Mikkel V.; FARRELL, Robert P.; HEDLEY, Simon J.; JUDD, Ted C.; KAYSER, Frank; (1266 pag.)WO2016/187308; (2016); A1;,
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