Category: ethers-buliding-blocks

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. 171290-52-1, name is 3,5-Dimethoxyphenylacetylene, A new synthetic method of this compound is introduced below., Safety of 3,5-Dimethoxyphenylacetylene

To a solution of 1.5 g (9.2 mmol) of 1-ethynyl-3,5-dimethoxybenzene and 2.16 g (9.2 mmol) of 4-iodoanisole in 10.0 mL of pyrrolidine, 64 mg (0.246 mmol) of triphenylphosphine and 27 mg (0.123 mmol) of Pd(OAc)2 were added. The mixture was stirred under an Ar stream and heated at reflux temperature for 1.0 h. The mixture was frozen and poured into 60 mL of saturated ammonium chloride solution and then extracted with 30 mL of CH2Cl2. The organic layer was washed with brine and dried (Na2SO4). After filtration, the residue was purified by flash column chromatography on silica gel, with hexane-EtOAc, 9:1 as the eluent, to give pure (4) in 93% yield.

The synthetic route of 171290-52-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lara-Ochoa, Francisco; Sandoval-Minero, Leticia C.; Espinosa-Perez, Georgina; Tetrahedron Letters; vol. 56; 44; (2015); p. 5977 – 5979;,
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Adding a certain compound to certain chemical reactions, such as: 261762-35-0, name is 5-Bromo-1,2-difluoro-3-methoxybenzene, 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 261762-35-0, name: 5-Bromo-1,2-difluoro-3-methoxybenzene

A solution of 1-bromo-3,4-difluoro-5-methoxy-benzene (1.11 g, 5.0 mmol, 1.0 eq.) and sodium methoxide (405 mg, 7.5 mmol, 1.5 eq.) in DMA (5 mL) is heated at 100C for lh. The reaction mixture is then poured into 60 ml. of water and ice, stirred and the resulting solid is filtered and dried under suction to afford the expected product.

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, 5-Bromo-1,2-difluoro-3-methoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GALAPAGOS NV; LES LABORATOIRES SERVIER; LABEGUERE, Frederic, Gilbert; HENG, Rama; ALVEY, Luke, Jonathan; AMANTINI, David; BREBION, Franck, Laurent; DE CEUNINCK, Frederic, Andre; DEPREZ, Pierre, Marc, Marie, Joseph; GOSMINI, Romain, Luc, Marie; JARY, Helene; PEIXOTO, Christophe; POP-BOTEZ, Iuliana, Ecaterina; VARIN, Marie, Laurence, Claire; (147 pag.)WO2017/211667; (2017); 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 658-89-9 as follows. Product Details of 658-89-9

4-[(Trifluoromethyl)oxy]-1 ,2-benzenediamine (commercially available, 1.03 g, 5.4 mmol) and urea (0.6 g, 10 mmol) in DMF were heated to 150 0C overnight and added to water (100 ml). The light brown solid precipitate was filtered off, washed with water and dried to give the desired product (1.1 g, 94%) which was used without further purification in the preparation of Intermediate 23.

According to the analysis of related databases, 658-89-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/129007; (2008); 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. 54149-17-6, name is 1-Bromo-2-(2-methoxyethoxy)ethane, This compound has unique chemical properties. The synthetic route is as follows., name: 1-Bromo-2-(2-methoxyethoxy)ethane

According to the literature [39], we followed the N-alkylation reaction to carry out the synthesis of compound 3. A 100mL round bottom flask was charged with intermediate 2 (1mmol), 1-bromo-2-(2-methoxyethoxy)ethane (2.2mmol) and sodium hydroxide (4mmol) in acetonitrile (15mL). The reaction mixture was stirred at 80C overnight. After removing the solvent, the residue was dissolved in dichloromethane. The organic solution was washed with water three times and then dried over anhydrous magnesium sulfate. Purified by column chromatography on silica gel with gradient eluents of petroleum ether and ethyl acetate, the pure target compound 3 was afforded.

According to the analysis of related databases, 54149-17-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Jiang, Kai; Chen, Si-Hong; Luo, Shi-He; Pang, Chu-Ming; Wu, Xin-Yan; Wang, Zhao-Yang; Dyes and Pigments; vol. 167; (2019); p. 164 – 173;,
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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. 349-65-5, name is 2-Methoxy-5-(trifluoromethyl)aniline, A new synthetic method of this compound is introduced below., Recommanded Product: 2-Methoxy-5-(trifluoromethyl)aniline

Step 3: To a solution of 2-methoxy-5-(trifluoromethyl)aniline (0.15 g) in anh CH2Cl2 (15 mL) at 0 C. is added CDI (0.13 g). The resulting solution is allowed to warm to room temp. over 1 h, is stirred at room temp. for 16 h, then is treated with 4-(2-(N-methylcarbamoyl)-4-pyridyloxy)aniline (0.18 g) from Step 2. The resulting yellow solution is stirred at room temp. for 72 h, then is treated with H2O (125 mL). The resulting aqueous mixture is extracted with EtOAc (2*150 mL). The combined organics are washed with a saturated NaCl solution (100 mL), dried (MgSO4) and concentrated under reduced pressure. The residue is triturated (90% EtOAc/10% hexane). The resulting white solids are collected by filtration and washed with EtOAc. The filtrate is concentrated under reduced pressure and the residual oil purified by column chromatography (gradient from 33% EtOAc/67% hexane to 50% EtOAc/50% hexane to 100% EtOAc) to give N-(2-methoxy-5-(trifluoromethyl)phenyl)-N’-(4-(2-(N-methylcarbamoyl)-4-pyridyloxy)phenyl) urea as a light tan solid: TLC (100% EtOAc) Rf 0.62; 1H NMR (DMSO-d6) delta 2.76 (d, J=4.8 Hz, 3H), 3.96 (s, 3H), 7.1-7.6 and 8.4-8.6 (m, 11H), 8.75 (d, J=4.8 Hz, 1H), 9.55 (s, 1H); FAB-MS m/z 461 ((M+H)+).

The synthetic route of 349-65-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER CORPORATION; US2003/207870; (2003); 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. 34967-24-3, name is 3,5-Dimethoxybenzyl amine, A new synthetic method of this compound is introduced below., Recommanded Product: 34967-24-3

To 3 mL of methanol solution containing 30 mg of 7-methoxy-4-methyl-1-(2-(4-oxocyclohexyl)ethyl)quinolin-2(1H)-one, 16 mg of 3,5-dimethoxybenzylamine, 8 muL of acetic acid and 9 mg of sodium cyanoborohydride were added, and the mixture was allowed to stand overnight after stirred at room temperature for 1 hour. To the reaction mixture, chloroform and aqueous saturated sodium hydrogen carbonate solution were added, the organic layer was separated, washed with aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by flash silica gel column chromatography [gradient elution of chloroform : methanol=90 : 10-80 : 20], to give 22 mg of 1-(2-(4-((2,4-dimethoxybenzyl)amino)cyclohexyl)ethyl)-7-methoxy-4-methylquinolin-2(1H)-one as a yellow oil. 1H-NMR (CDCl3) delta: 1.00-1.80 (7H, m), 1.88-2.04 (2H, m), 2.20-2.75 (3H, m), 2.41 (3H, s), 3.78-3.83 (2H, m), 3.79 (6H, s), 3.91 (3H, s), 4.20-4.30 (2H, m), 6.42-6.45 (3H, m), 6.77-6.85 (2H, m), 7.14-7.18 (1H, m), 7.61 (1H, d, J=9.0 Hz)

The synthetic route of 34967-24-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TOYAMA CHEMICAL CO., LTD.; TAISHO PHARMACEUTICAL CO., LTD; EP1900732; (2008); A1;,
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Electric Literature of 1535-73-5, A common heterocyclic compound, 1535-73-5, name is 3-Trifluoromethoxyaniline, molecular formula is C7H6F3NO, 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.

EXAMPLE 7; [5-(3-{4-[3-(Trifluoromethoxy)phenyllpiperazin-l-yl}isoxazol-5-yl)-2//-tetrazol-2-yllacetic acid; Step 1 : l-[3-(Trifluoromethoxy)phenvnpiperazine; A mixture of 3-(trifluoromethoxy)aniline (2.13 g, 12.0 mmol), bis(2- chloroethyl)amine hydrochloride (2.14 g, 12.00 mmol) and 2-(2-ethoxyethoxy)ethanol (3.0 mL) was heated at 160 °C for 6 h. After being cooled to room temperature, the mixture was poured into a 250 mL separatory funnel containing aqueous 1 N NaOH solution (100 mL) and extracted with MTBE (2 x 50 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. Purification by column chromatography through silica gel, eluting with 100percent CH2Cl2 to 80:20:3 CH2Cl2:EtOH:NH4OH, to afford the title compound as a light yellow oil. MS (ESI, Q+) m/z 247 (M + 1).

The synthetic route of 1535-73-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK FROSST CANADA LTD.; ISABEL, Elise; LACHANCE, Nicolas; LECLERC, Jean-Philippe; LEGER, Serge; OBALLA, Renata, M.; POWELL, David; RAMTOHUL, Yeeman, K.; ROY, Patrick; TRANMER, Geoffrey, K.; ASPIOTIS, Renee; LI, Lianhai; MARTINS, Evelyn; WO2010/94126; (2010); A1;,
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Electric Literature of 450-88-4, 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. 450-88-4, name is 1-Bromo-4-fluoro-2-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows.

Intermediate Example Int17.031 -(4-bromo-3-methoxyphenyl)-4-ieri-butylpiperazineTo a stirred solution of 1 -tert-butylpiperazine (5.0 g) in THF (25 mL) was added n-butyllithium in hexanes (4.2 mL, c = 2.5 M) at -78C. The solution was stirred for 30 min at 0C. A solution of 1 -bromo-4-fluoro-2-methoxybenzene (1.44 g) in THF (2 mL) was added at -78 C and the reaction mixture was allowed to warm up to 0 C over 3 h. The mixture was stirred at 0 C 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. Aminophase-silica-gel chromatography gave 490 mg of the title compound.

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

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; SCHULZE, Volker; KOSEMUND, Dirk; WENGNER, Antje, Margret; SIEMEISTER, Gerhard; STOeCKIGT, Detlef; LIENAU, Philip; BRIEM, Hans; WO2012/160029; (2012); 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. 886762-08-9, name is 5-Bromo-2-(trifluoromethoxy)aniline, A new synthetic method of this compound is introduced below., category: ethers-buliding-blocks

Preparation 7; 4-(4-Methyl-piperazin-1-yl)-2-trifluoromethoxy-phenylamine; Tris(dibenzilideneacetone)dipalladium, Pd2(dba)3(1.1 g, 1.2 mmol), 2-dicyclohexylphosphino-2′-(N,N- dimethylamino)-biphenyl (0.94 g, 2.4 mmol), 5-bromo-2-trifluoromethoxy-phenylamine (30.7 g, 120 mmol) in THF (50 mL) were charged in a round-bottom flask flushed with argon. The flask was evacuated and backfilled with argon. LiN(TMS)2 solution (1 M in THF, 288 mL) and N-methylpiperazine (26.7 mL, 194 mmol) were added and the reaction refluxed for 1 h. The reaction mixture was then allowed to cool to room temperature and filtered through a pad of celite. The organic phase was concentrated, the residue dissolved in DCM (200 mL) and washed with water (1 x 100 mL). The organic phases were dried over anhydrous Na2SU4, the solvent evaporated in vacuo and the crude solid was purified by flash chromatography on silica gel (eluant: DCM/EtOH 90/10) to afford 23 g of 4-(4- methyl-piperazin-1-yl)-2-trifluoromethoxy-phenylamine (70% yield) as a light brown powder. MS calc: 276.1318; MS found: 276.1320

The synthetic route of 886762-08-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NERVIANO MEDICAL SCIENCES S.R.L.; WO2009/156315; (2009); A1;,
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Electric Literature of 19056-40-7, A common heterocyclic compound, 19056-40-7, name is 4-Bromo-3-methoxyaniline, molecular formula is C7H8BrNO, 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 suspension of 4-bromo-3-methoxyaniline (2.5 g, 12.4 mmol) and potassium phosphate, tribasic (1.08 g, 6.19 mmol) in acetonitrile (40 mL) at 0°C, was added 2,4- dibromobutyryl chloride (1.64 mL, 12.4 mmol). The mixture was brought to rt and stirredfor 1 h. Aqueous NaOH (50percent) (5 mL, 12.37 mmol) was added, and the mixture was stirred at rt for 4 h. The reaction mixture was filtered through CELITE®, which was rinsed with acetonitrile. The filtrate was concentrated. The product was purified by flash chromatography (0-50percent EtOAc/Hex gradient) to obtain Intermediate 4 (3.5 g, 66percent yield) as a pinkish colored solid. MS(ESI) m/z: 350.0 (M+H) ?H NMR (300 MHz, chloroform-d) oe ppm 7.77 (d, J=2.27 Hz, 1 H) 7.53 (d, J=8.69 Hz, 1 H) 6.82 (dd, J=8.69, 2.27 Hz, 1 H) 4.61 (dd, J=7.18, 3.40 Hz, 1 H) 4.05 (dt, J=9.73, 7.22 Hz, 1 H) 3.94 (s, 3 H) 3.85 (ddd, J10.01, 7.55, 2.83 Hz, 1 H) 2.69 – 2.83 (m, 1 H) 2.48 (ddt, J=14.35, 6.70, 3.26, 3.26 Hz, 1 H).

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; BRISTOL-MYERS SQUIBB COMPANY; GLUNZ, Peter W.; SITKOFF, Doree F.; BODAS, Mandar Shrikrishna; YADAV, Navnath Dnyanoba; PATIL, Sharanabasappa; RAO, Prasanna Savanor Maddu; THIYAGARAJAN, Kamalraj; MAISHAL, Tarun Kumar; (498 pag.)WO2016/144936; (2016); A1;,
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