Month: May 2021

Synthetic Route of 169247-46-5,Some common heterocyclic compound, 169247-46-5, name is 1-(Benzyloxy)-4-bromo-2-(trifluoromethyl)benzene, molecular formula is C14H10BrF3O, 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.

Then, 5.10 g of 4-bromo-2-trifluoromethyl-1-benzyloxybenzene, 2.34 g of p-ethoxyphenol, 2.13 g of potassium carbonate, 100 mg of copper and 200 mg of cuprous chloride were charged into a reaction vessel, and stirred at 130° C. to 140° C. for 5 hours. The reaction solution was cooled to room temperature, poured into ice-water and then acidified by adding 10percent hydrochloric acid. The solution was extracted twice with 100 ml of diethyl ether. Then, the ether layers were combined, washed with water, dried over anhydrous magnesium sulfate and concentrated to give a crude product. This crude product was subjected to silica gel chromatography to give 2.50 g of 2-trifluoromethyl-4-(4-ethoxyphenoxy)-1-benzyloxybenzene (yield, 41percent).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-(Benzyloxy)-4-bromo-2-(trifluoromethyl)benzene, its application will become more common.

Reference:
Patent; Sumitomo Chemical Company, Limited; US5530015; (1996); A;,
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Application of 92028-21-2, 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. 92028-21-2 name is 6-Methoxy-[1,1′-biphenyl]-3-amine hydrochloride, 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.

Example 6 N-(4-Methoxy-3-phenyl)phenyl-(2-chloro-5-nitrophenyl)carboxamide The title compound (0.586 g) was obtained as a crystalline solid according to the procedure described in Example 2 using (4-methoxy-3-phenyl)aniline hydrochloride (0.478 g), pyridine (5 ml) and 2-chloro-5-nitrobenzoyl chloride (0.535 g). 1H-NMR (400 MHz, CDCl3, TMS): delta(ppm) 3.95 (3H, s), 7.31-7.46 (4H, m), 7.63-7.69 (3H, m), 8.27 (1H, dd, J=8.8, 2.7 Hz), 8.67 (1H, d, J=2.7 Hz), 8.54 (1H, d, 2.2 Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Methoxy-[1,1′-biphenyl]-3-amine hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; SANKYO COMPANY, LIMITED; US2003/134859; (2003); A1;,
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Related Products of 2106-18-5, These common heterocyclic compound, 2106-18-5, name is 2-(Trifluoromethoxy)fluorobenzene, 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 500 mL three-necked flask, concentrated sulfuric acid (20 mL, 0.35 mol, 3.5 eq)The raw material o-fluorotrifluoromethoxybenzene (18 g, 0.1 mol, 1 eq) was added portionwise with stirring,After stirring for half an hour the solution is clear,Cool to -5 C with ice-salt bath,Concentrated nitric acid (6.6 mL, 0.1 mol, 1 eq) was slowly added dropwise,The reaction is exothermic, the dropping rate to maintain the internal temperature does not exceed 0 ,After the addition is completed,After stirring at 0 C for 1 hour,Heated to 40 C and stirred for 12h,After the reaction solution was cooled to room temperature,Slowly poured into crushed ice, and constantly stirring,A large number of yellow solid precipitation, suction filtration,The filter cake was washed three times with water, drained,Dried under vacuum to give a yellow solid 18g, yield 80%, HPLC purity 95%.

The synthetic route of 2106-18-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wuxi Jiehua Pharmaceutical Technology Co., Ltd.; Bao Liang; Gu Shuyin; (7 pag.)CN106986886; (2017); A;,
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Reference of 169247-46-5, These common heterocyclic compound, 169247-46-5, name is 1-(Benzyloxy)-4-bromo-2-(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.

A 100 mL round bottom flask was charged with EXAMPLE 49B (1.9Og, 5.74 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(l,3,2-dioxaborolane) (1.75g, 6.89 mmol), [l,r-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane (0.234 g, 0.287 mmol), diphenylphosphinoferrocine (0.159g, 0.287 mmol) and potassium acetate (1.689g, 17.21 mmol) in 50 mL dioxane. The mixture was degassed with N2 and heated at 800C overnight, diluted with water, and extracted into ethyl acetate. The organics were washed with brine and dried (MgSO4), filtered, and concentrated. The crude product was purified on silica gel eluting with 0-10percent ethyl acetate/hexane to provide the title compound. MS (DCI(+)) m/e 396 (M+NH4)+; 1H NMR (300 MHz, dimethylsulfoxide- d6) delta ppm 7.64 (dd, 1 H), 7.56-7.16 (m, 7 H), 5.26 (s, 2 H), 1.29 (s, 12 H).

The synthetic route of 169247-46-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBOTT LABORATORIES; CLARK, Richard, F.; BELL, Randy, L.; BA-MAUNG, Nwe, Y.; ERICKSON, Scott, A.; FIDANZE, Steve, D.; MANTEI, Robert, A.; SHEPPARD, George, S.; SORENSEN, Bryan, K.; WANG, Gary, T.; WANG, Jieyi; WO2010/138576; (2010); 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. 6850-60-8, name is (4-Ethoxyphenyl)methanamine, A new synthetic method of this compound is introduced below., Safety of (4-Ethoxyphenyl)methanamine

General procedure: benzylamines (1, 0.2 mmol), 1,3-dicarbonyl derivatives (2,0.3 mmol), NIS (0.4 mmol), TBHP (0.6 mmol), Na2CO3 (0.4 mmol) were mixed under N2 atmosphere in 2 mL DMA. The reaction tube was heated in an oil bath at 50 C for 16 hours. After completion of the reaction, the reaction mixture was extracted with EtOAc (15 mL × 3), and the solvent was removed under reduced pressure. The remaining crude product was then purified through column chromatography using silica gel (ethyl acetate/petroleum ether = 1/10) to afford 3.

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:
Article; Li, Fei; Liu, Xiaolan; Yang, Shengxiang; Yang, Yuzhu; Tetrahedron Letters; (2020);,
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Related Products of 151414-47-0, 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. 151414-47-0, name is 2,6-Difluoro-4-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows.

Synthesis example 31 : A -(2,6-Difluoro-4-methoxy-phenyl)-5-(2,5-dimethoxyphenyl)-1-methyl-1H- pyrazole-3-carboxylic acid amide To a solution of intermediate 2b (72 mg) in dry toluene (2 mL) were consecutively added 2,6-difluoro-4- methoxyaniline (48 mg) and trimethyl aluminium (2 M in heptane, 0.15 mL) and the resulting mixture was heated to 110 C for 1 h. The mixture was chilled and 1 M HCI (2 mL) was added. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried and the volatiles were removed under reduced pressure. The residue was purified through washing with Et20 to give the desired compound (86% yield). LC-MS (Method 2): m/z [M+Hf = 404.1 (MW calc. = 403.38); R, = 0.74 min

The chemical industry reduces the impact on the environment during synthesis 2,6-Difluoro-4-methoxyaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GRUeNENTHAL GMBH; NORDHOFF, Sonja; WACHTEN, Sebastian; KLESS, Achim; VOSS, Felix; RITTER, Stefanie; WO2014/108336; (2014); A1;,
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Reference of 887267-47-2, 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 887267-47-2 as follows.

General procedure: Triphosgene (0.09 g, 0.3 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 (0.16 g, 0.7 mmol) in anhydrous CH2Cl2 (10 mL) was added dropwise to the above mixture and stirring continued for 20 min. Et3N (0.12 mL, 0.89 mmol) diluted with CH2Cl2 (5 mL) was then added into the mixture. Stirring was continued for 20 min and a solution of Et3N (0.12 mL, 0.89 mmol), compound (9) (0.2 g, 0.74 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 = 3:1) yielding (W1).

According to the analysis of related databases, 887267-47-2, the application of this compound in the production field has become more and more popular.

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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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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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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Reference of 15799-79-8, These common heterocyclic compound, 15799-79-8, name is 3-Methoxy-N,N-dimethylaniline, 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.

[0134] (R)-4-Oxo-2-(4-dimethylamino-2-methoxyphenyl)-butyric acid methyl ester (Table 2, entries 11 & 12): To an amber 2-dram vial equipped with a magnetic stir bar was added (2S, 5S)-5-benzyl-2-tert-butyl-3-methylimidazolidin-4-one (6.13 mg, 0.0250 mmol, 0.100 equiv), 4-methyl ester (28.5 mg, 0.250 mmol, 1.00 equiv), CHCl3 (0.25 ml), HCl (as a 4N solution in 1,4-dioxane, 6.25 uL, 0.0250 mmol, 0.100 equiv), and 3-dimethylamino-anisole (44 uL, 0.30 mmol, 1.2 equiv). The solution was stirred for 5 min at ambient temperature and subjected directly to silica gel chromatography. Gradient elution with 20-40% EtOAc in hexanes afforded the product as a colorless oil in 73% yield (48.2 mg, 0.182 mmol); 91% ee. IR (film) 2950, 2903, 2838, 2727, 1730, 1616, 1569, 1519, 1462, 1440, 1356, 1242, 1171, 1114, 1033, 979.4, 814.6, 642.5 cm-1; 1H NMR (300 MHz, CDCl3) ?9.77 (t, J=1.1 Hz, 1H, CHO), 6.99 (d, J=8.2 Hz, 1H, ArH), 6.27 (dd, J=2.5, 8.5 Hz, 1H, ArH), 6.22 (d, J=2.5 Hz, 1H, ArH) 4.38 (dd, J=5.2, 9.1 Hz, 1H, ArCH), 3.81 (s, 3H, ArOCH3), 3.66 (s, 3H, CO2CH3), 3.52 (ddd, J=1.4, 9.1, 18.1 Hz, 1H, CH2CO), 2.94 (s, 6H, N(CH3)2), 2.67 (ddd, J=0.8, 4.9, 17.8 Hz, 1H CH2CO); 13C NMR (75 MHz, CDCl3) ?201.0, 174.4, 157.5, 151.5, 129.3, 114.6, 104.9, 96.2, 55.6, 52.5, 46.7, 40.9, 39.2. HRMS (CI) exact mass calcd for (C21H23NO3) requires m/z 266.1392 for [M+H]+, found m/z 266.1387. [?]D=-149.0 (c=1.0, CHCl3). [0135] The enantiomeric ratio of the product was determined by HPLC analysis of the corresponding alcohol (obtained by NaBH4 reduction in ethanol at 0o C.) using a Chiracel AD and AD guard column (6.0% ethanol/hexanes, 1 mL/min); S isomer tr=26.0 min, R isomer tr=27.8 min. The same reaction conducted at -20o C. on 0.5-mmol scale was complete after 8 h and purified in identical fashion to give the product in 90% yield (119 mg, 0.448 mmol) and 92% ee. EXAMPLE 8 [0104] (R)-4-Oxo-2-(4-dimethylamino-2-methoxyphenyl)-butyric acid methyl ester (Table 1, entry 6): To an amber 2-dram vial equipped with a magnetic stir bar was added (2S,5S)-5-benzyl-2-tert-butyl-3-methylimidazolidin-4-one (6.13 mg, 0.0250 mmol, 0.100 equiv), CHCl3 (0.25 ml), HCl (as a 4N solution in 1,4-dioxane, 6.25 uL, 0.0250 mmol, 0.100 equiv), and 3-dimethylamino-anisole (44 uL, 0.30 mmol, 1.2 equiv). The solution was cooled to -20o C. before oxobutenoic acid methyl ester (28.5 mg, 0.250 mmol, 1.00 equiv) was added. The resulting solution was maintained at -20o C. for 8 h and then subjected directly silica gel chromatography. Gradient elution with 20-40% EtOAc in hexanes afforded the product as a colorless oil in 73% yield (48.2 mg, 0.182 mmol); 91% ee. IR (film) 2950, 2903, 2838, 2727, 1730, 1616, 1569, 1519, 1462, 1440, 1356, 1242, 1171, 1114, 1033, 979.4, 814.6, 642.5 cm-1; 1H NMR (300 MHz, CDCl3) ?9.77 (t, J=1.1 Hz, 1H, CHO), 6.99 (d, J=8.2 Hz, 1H, ArH), 6.27 (dd, J=2.5, 8.5 Hz, 1H, ArH), 6.22 (d, J=2.5 Hz, 1H, ArH), 4.38 (dd, J=5.2, 9.1 Hz, 1H, ArCH), 3.81 (s, 3H, ArOCH3), 3.66 (s, 3H, CO2CH3), 3.52 (ddd, J=1.4, 9.1, 18.1 Hz, 1H, CH2CO), 2.94 (s, 6H, N(CH3)2), 2.67 (ddd, J=0.8, 4.9, 17.8 Hz, 1H, CH2CO); 13C NMR (75 MHz, CDCl3) ?201.0, 174.4, 157.5, 151.5, 129.3, 114.6, 104.9, 96.2, 55.6, 52.5, 46.7, 40.9, 39.2. HRMS (CI) exact mass calcd for (C21H23NO3) requires m/z 266.1392 for [M+H]+, found m/z 266.1387. [?]D=-149.0 (c=1.0, CHCl3). The enantiomeric ratio of the product was determined by HPLC analysis of the corresponding alcohol (obtained by NaBH4 reduction in ethanol at 0o C.) using a Chiracel AD and AD guard column (6.0% ethanol/hexanes, 1 mL/min); S isomer tr=26.0 min, R isomer tr=27.8 min.

The synthetic route of 15799-79-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MacMillan, David W.C.; Paras, Nick A.; US2003/236438; (2003); A1;,
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