Tag: M.W=200-300

Application of 204452-91-5, A common heterocyclic compound, 204452-91-5, name is 7-(Dimethoxymethyl)-1,2,3,4-tetrahydro-1,8-naphthyridine, molecular formula is C11H16N2O2, 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.

Step 3: Preparation of 6-bromo-7-(dimethoxymethyl)-1,2,3,4-tetrahydro-1,8-naphthyridine NBS (38.3 g, 215 mmol) was added in batches to a solution of 7-(dimethoxymethyl)-1,2,3,4-tetrahydro-1,8-naphthyridine (42.7 g, 205 mmol) in MeCN (1 L) at room temperature. The reaction solution stirred for 1 hour and concentrated. The resulting residue was dissolved in CH2Cl2, washed with 1 M NaOH aqueous solution and saturated brine successively, dried over anhydrous sodium sulfate and concentrated. The resulting residue was subjected to column chromatography to obtain the title compound 6-bromo-7-(dimethoxymethyl)-1,2,3,4-tetrahydro-1,8-naphthyridine (47.5 g, total yield of three steps: 81%). 1H NMR (400 MHz, CDCl3): delta 7.27 (s, 1H), 5.55 (s, 1H), 5.39 (br s, 1H), 3.45 (s, 6H), 3.38 (m, 2H), 2.70 (t, J = 6.0 Hz, 2H), 1.88 (m, 2H); MS m/z (ESI): 287.0 [M+H]+.

The synthetic route of 204452-91-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu Hansoh Pharmaceutical Group Co., Ltd.; Shanghai Hansoh Biomedical Co., Ltd.; GAO, Peng; XIU, Wenhua; WANG, Shaobao; LIU, Lei; BAO, Rudi; (94 pag.)EP3444250; (2019); A1;,
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Synthetic Route of 32338-02-6, The chemical industry reduces the impact on the environment during synthesis 32338-02-6, name is 2-Bromo-4-methoxyaniline, I believe this compound will play a more active role in future production and life.

General procedure: A mixture of benzyl 1-oxa-6-azaspiro[2.5]octane-6-carboxylate (247 mg, 1.0 mmol), 2-bromo-4-methoxyaniline (303 mg, 1.5 mmol) and lithium perchlorate (190 mg, 1.7 mmol) were taken in acetonitrile (3.0 mL). The reaction mixture was heated to 90 °C for 18 h. The reaction mixture was diluted with ethyl acetate (20 mL) and washed with water. The organic layer was dried over sodium sulfate and concentrated under reduced pressure, and the product was purified by column chromatography (silica gel, 50percent EtOAc/hexanes) to provide benzyl 4-(((2-bromo-4-methoxyphenyl)amino)methyl)-4-hydroxypiperidine-1-carboxylate, 5c (358 mg, 80percent) as a colourless syrup.

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, 2-Bromo-4-methoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kurissery, A. Tony; Rajkumar, G. Abraham; Arvapalli, Venkata Satyanarayana; Pitchumani, Venkatachalam; Tetrahedron Letters; vol. 58; 37; (2017); p. 3607 – 3611;,
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Related Products of 27060-75-9, 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. 27060-75-9, name is 1-Bromo-4-methoxy-2-methylbenzene, This compound has unique chemical properties. The synthetic route is as follows.

To a CCl4 solution (125 mL) of 2-bromo-5-methoxytoluene (0.050 mol) and NBS (0.055 mol) was added AIBN (0.001 mol), and the mixture was stirred at 80 C for 18 h. The mixture was diluted with hexane before filtration through a Celite pad. Evaporation of the solvent followed by washing of the residue with ethyl acetate gave 4-bromo-3-(bromomethyl)anisole.

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-4-methoxy-2-methylbenzene. I believe this compound will play a more active role in future production and life.

Reference:
Article; Yoshida, Hiroto; Yoshida, Ryuma; Mukae, Masashi; Ohshita, Joji; Takaki, Ken; Chemistry Letters; vol. 40; 11; (2011); p. 1272 – 1274;,
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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 54314-84-0 as follows. category: ethers-buliding-blocks

To a solution of – uoro- , – y roxy- enza e y e (11.15 g, 71.42 mmol) in anhydrous DMSO (88 mL) under nitrogen were added sequentially sodium t-butoxide (13.72 g, 142.84 mmol) and benzyl-3-bromopropyl ether (17.29 g, 78.56 mmol) and the reaction mixture stirred at rt for 18 h. The mixture was diluted with water (400 mL) and extracted with EtOAc (4×100 mL). The combined organic layer was washed with water and brine, dried over MgS04, filtered and concentrated in vacuo. Purification was completed by flash chromatography (20percent EtOAc / hexane). Yield 11.5 g (77 percent).1H NMR (400 MHz, CHLOROFORM-^) delta ppm 11.62 (s, 1 H), 10.23 (s, 1 H), 7.42 – 7.16 (m, 5 H), 7.05 (dd, J=8.8, 5.3 Hz, 1 H), 6.54 (t, J=9.6 Hz, 1 H), 4.52 (s, 2 H), 4.13 (t, J=6.3 Hz, 2 H), 3.68 (t, J=6.1 Hz, 2 H), 2.12 (quin, J=6.2 Hz, 2 H). 19F NMR (376 MHz, CHLOROFORM- d): -132 ppm.

According to the analysis of related databases, 54314-84-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ANACOR PHARMACEUTICALS, INC.; HERNANDEZ, Vincent, S.; DING, Charles; PLATTNER, Jacob, J.; ALLEY, Michael Richard, Kevin; ROCK, Fernando; ZHANG, Suoming; EASOM, Eric; LI, Xianfeng; ZHOU, Ding; WO2012/33858; (2012); A2;,
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Synthetic Route of 5905-69-1, 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. 5905-69-1, name is 1-Bromo-4-(difluoromethoxy)benzene, This compound has unique chemical properties. The synthetic route is as follows.

Example 346: Ethyl (2E)-3-{1-[4-(difluoromethoxy)phenyl]-3-(2-phenylethyl)-1H-indol-5-yl}propenoate; To a solution of the compound obtained at Example 141 (200 mg) in n-butyl acetate (15 ml) were added 1-bromo-4-(difluoromethoxy)benzene (281 mg), palladium acetate (28 mg), 2-(di-tert-butylphosphino)biphenyl (75 mg) and tripotassium phosphate (535 mg), and the mixture was heated and stirred at 120C for 12 hours. The reaction mixture was cooled to room temperature, then the insolubles were filtered off, the filtrate was distilled off in vacuo and the residue obtained was purified by silica gel column chromatography (hexane:ethyl acetate=19:1 to 9:11) to afford the above-identified compound (227 mg).

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-4-(difluoromethoxy)benzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Asubio Pharma Co., Ltd.; EP2141148; (2010); A1;,
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Synthetic Route of 873980-68-8, These common heterocyclic compound, 873980-68-8, name is 4-Bromo-2-methoxy-5-methylaniline, 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.

Step 2: BBr3 (1 M solution in CH2CI2, 138 mL, 138 mmol) was added to a solution of the intermediate of step 1(12.0 g, 55.6 mmol) in CH2CI2 at OC and the mixture was stirred rt for 10 h. Aq. NaHCO3 was added and the mixture was extracted with CH2CI2. The combined organic layers were washed with water, brine, were dried the volatiles were removed under reduced pressure. The residue was purified by chromatography (SiC2, Cy/EtOAc) to yield the desired compound (10 g, 89%).

The synthetic route of 873980-68-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GRUeNENTHAL GMBH; NORDHOFF, Sonja; VOSS, Felix; WACHTEN, Sebastian; KLESS, Achim; RITTER, Stefanie; WO2015/90580; (2015); A1;,
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Reference of 204452-91-5, 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. 204452-91-5, name is 7-(Dimethoxymethyl)-1,2,3,4-tetrahydro-1,8-naphthyridine, This compound has unique chemical properties. The synthetic route is as follows.

Compound 13c (0.73 g) was dissolved in trifluoroacetic acid (5 mL). The resulting mixture was allowed to stir at room temperature under argon for 1.5 hours. The mixture was concentrated. The residue was dissolved in methylene chloride and washed 2× with saturated sodium bicarbonate solution. The organic layer was dried over magnesium sulfate, filtered, and the filtrate was concentrated to obtain compound 13d.

The chemical industry reduces the impact on the environment during synthesis 7-(Dimethoxymethyl)-1,2,3,4-tetrahydro-1,8-naphthyridine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Flores, Christopher M.; Wade, Paul R.; US2011/319400; (2011); A1;,
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Adding a certain compound to certain chemical reactions, such as: 588-96-5, name is p-Bromophenetole, 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 588-96-5, Safety of p-Bromophenetole

To a solution of tert-butyl 4-(piperazinyisulfonyl)perhydro-2H-pyran-4-carboxyate (715 mg, 2.14 mmol, supplied by CarboGen) in toluene (15 mL) under N2 were added 1-bromo-4-ethoxybenzene (473 mg, 2.35 mmol), sodium tert-butoxide (514 mg, 5.35 mmol), palladium(II) acetate (5.0 mg, 0.021 mmol), and tri-tert-butylphosphine (3.5 mg, 0.17 mmol). The reaction was continued overnight at 60 C. under N2. No starting material remained at this time, so the reaction mixture was diluted with methanol and concentrated under reduced pressure. The residue was partially dissolved in dichloromethane and filtered. The filtrate was concentrated under reduced pressure, and the resulting dark material was triturated with diethyl ether to produce a white solid, which was collected by suction filtration to produce 640 mg of clean product (66%). 1H NMR and mass spectrometry (MH+=455) were consistent with the desired structure.

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:
Patent; Barta, Thomas E.; Becker, Daniel P.; Bedell, Louis J.; Boehm, Terri L.; Brown, David L.; Carroll, Jeffery N.; Chen, Yiyuan; Fobian, Yvette M.; Freskos, John N.; Gasiecki, Alan F.; Grapperhaus, Margaret L.; Heintz, Robert M.; Hockerman, Susan L.; Kassab, Darren J.; Khanna, Ish K.; Kolodziej, Stephen A.; Massa, Mark A.; McDonald, Joseph J.; Mischke, Brent V.; Mischke, Deborah A.; Mullins, Patrick B.; Nagy, Mark A.; Norton, Monica B.; Rico, Joseph G.; Schmidt, Michelle A.; Stehle, Nathan W.; Talley, John J.; Vernier, William F.; Villamil, Clara I.; Wang, Lijuan J.; Wynn, Thomas A.; US2005/9838; (2005); A1;,
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Synthetic Route of 5414-19-7, 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. 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a stirred solution of 3-amino-l-brotaunoisoquinoline (444 mg, 2.00 mmol) in anhydrous dimethylformamide (10175 mL) was added sodium hydride (60%, unwashed, 96 mg, 2.4 mmol) in one portion. The mixture was stirred at 25 0C for 5 min before 2-bromoethyl ether (90%, 250 DL, 2.00 mmol) was added. The mixture was stirred at 25 0C for 5 h and at 75 0C for 72 h before it was cooled to 25 0C, quenched with saturated ammonium chloride solution and diluted with ethyl acetate. The organic layer was separated, washed with water and brine, dried with Na2SO4, filtered and concentrated. Purification of the residue on silica gel eluting with 0% to 70% ethyl acetate/hexanes afforded Cap-143, step a as a yellow solid (180 mg, 31%) . Rt = 1.75 min (Cond. -MS-Wl) ; 90% homogenity index; LCMS: Anal. CaIc. for [M+H] + C13H14BrN2O: 293.03; found: 293.04.

The synthetic route of 1-Bromo-2-(2-bromoethoxy)ethane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LAVOIE, Rico; BENDER, John A.; BACHAND, Carol; RUEDIGER, Edward H.; KADOW, John F.; WO2010/120621; (2010); A1;,
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Related Products of 5905-69-1, 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 5905-69-1 as follows.

A. 2-(4-(difluoromethoxy)phenyl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolaneA mixture of commercially available l-bromo-4-(difluoromethoxy)benzene (1 g, 4.48 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(l,3,2-dioxaborolane) (1.2g, 4.71 mmol), potassium acetate (1.3 g, 13.4 mmol), and PdCl2(dppf)-CH2Cl2 Adduct (0.18 g, 0.22 mmol) in DMF (15 mL) was stirred under nitrogen at 90 0C for 1 hour. Diluted with DCM, washed with water, sat. NaHCC^, brine, dried (MgSC^), and concentrated.The crude was purified using ISCO flash chromatography (silica gel/ hexanes/ethyl acetate 100:0 to 50:50 gradient) to afford the desired product 2-(4- (difluoromethoxy)phenyl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane 13A (1.12 g, 3.32 mmol, 74.0 % yield) as a brown oil.

According to the analysis of related databases, 5905-69-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; AHMAD, Saleem; WASHBURN, William, N.; HERNANDEZ, Andres, S.; ROBL, Jeffrey, A.; NGU, Khehyong; WANG, Zhenghua; WO2010/104830; (2010); A1;,
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