Ethers-buliding-blocks

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. 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 20781-20-8

General procedure: The solution of l-(benzyloxy)-6-bromo-3-((2,4-difluorobenzyl)carbamoyl)-2-oxo-l,2-dihydro-l,8- naphthyridin-4-yl 4-methylbenzenesulfonate (7; 0.2 mmol), N-ethyl-N-isopropylpropan-2-amine (2.0 mmol) and amine (1.0 mmol) in DMF (2.0 mL) was heated to 50 C for 1 hr. The reaction mixture was cooled to room temperature and purified by Combiflash. Compound 4-substituted l-(benzyloxy)-6-bromo- N-(2,4-difluorobenzyl)-2-oxo-l,2-dmydro-l,8-naphthyridine-3-carboxamide (8) was afforded.According to general procedure A, the title compound was prepared in 89 % yield from l-(benzyloxy)-6- bromo-3-((2,4-difluorobenzyl)carbamoyl)-2-oxo-l,2-dihydro-l,8-naphthyridin-4-yl 4- methylbenzenesulfonate (7). NMR (400 MHz, CDCI3) delta 12.05 (t, 7 = 6.2 Hz, 1H), 10.61 (t, 7 = 5.7 Hz, 1H), 8.58 (d, 7 = 2.1 Hz, 1H), 8.34 (d, 7 = 2.2 Hz, 1H), 7.57 (dd, 7 = 7.3, 1.9 Hz, 2H), 7.39 – 7.22 (m, 4H), 7.17 (dd, 7 = 8.9, 4.3 Hz, 1H), 6.85 – 6.63 (m, 2H), 6.47 – 6.34 (m, 2H), 5.15 (s, 2H), 4.64 (d, 7 = 6.3 Hz, 2H), 4.52 (d, 7 = 5.7 Hz, 2H), 3.74 (s, 3H), 3.73 (s, 3H)

The synthetic route of 20781-20-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES; ZHAO, Xue, Zhi; SMITH, Steven; METIFIOT, Mathieu, A.; JOHNSON, Barry; MARCHAND, Christophe; HUGHES, Stephen; POMMIER, Yves; BURKE, Terrence, R.; WO2014/186398; (2014); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

702-24-9, Adding a certain compound to certain chemical reactions, such as: 702-24-9, name is 4-Methoxy-N-methylbenzylamine, 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 702-24-9.

General procedure: A solution of N-heterocycle compound (0.2 mmol) and graphene oxide (GO) (8 mg) in N,N-dimethylformamide(1.0 mL) was stirred in a sealed tube under an atmosphere of argon at 150 ¡ãC for 18 h. After being cooled to room temperature,the reaction mixture was filtered and washed with ethyl acetate (20 mL). Afterward, 10 mL water was added tothe solution and extracted with ethyl acetate (3 ¡Á 15 mL), the combined organic layers were dried over anhydrous Na2SO4.The solvent was evaporated under vacuum and the crude product was purified by preparative thin-layer chromatography (TLC) on silica gel with petroleum ether and ethyl acetate to achieve the pure product.

According to the analysis of related databases, 702-24-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ma, Juan; Zhang, Jingyu; Zhou, Xiao; Wang, Jiawei; Gong, Hang; Journal of the Iranian Chemical Society; vol. 15; 12; (2018); p. 2851 – 2860;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

5905-69-1, These common heterocyclic compound, 5905-69-1, name is 1-Bromo-4-(difluoromethoxy)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.

(Reference Example 71) Ethyl 1-[4-(difluoromethoxy)phenyl]piperidine-4-carboxylate[0521] Sodium tert-butoxide (2.29 g, 23.8 mmol), palladium(II) acetate (428 mg, 1.91 mmol), and tri-tert-butylphosphine (370 muL, 1.52 mmol) were added to a solution of ethyl piperidine-4-carboxylate (3.52 mL, 22.9 mmol) and 1-bromo-4-(difluoromethoxy)benzene (4.25 g, 19.1 mmol) in toluene (122 mL), and the mixture was stirred at 80C for 30 minutes. Water was added to the reaction solution, followed by extraction with ethyl acetate. The obtained organic layer was washed with brine and then dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography [elute: hexane/ethyl acetate = 100/0 – 90/10] to obtain the title compound (3.17 g, yield: 56%). [0523] 1H-NMR (400 MHz, CDCl3) delta: 7.07-7.00 (2H, m), 6.95-6.87 (2H, m), 6.41 (1H, t, J = 75 Hz), 4.16 (2H, q, J = 7 Hz), 3.61-3.55 (2H, m), 2.84-2.73 (2H, m), 2.47-2.39 (1H, m), 2.08-1.99 (2H, m), 1.95-1.83 (2H, m), 1.27 (3H, t, J = 7 Hz).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 5905-69-1.

Reference:
Patent; Daiichi Sankyo Company, Limited; KOBAYASHI, Hideki; OHKAWA, Nobuyuki; TAKANO, Daisuke; KUBOTA, Hideki; ONODA, Toshio; KANEKO, Toshio; ARAI, Masami; TERASAKA, Naoki; EP2862861; (2015); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

136-90-3, The chemical industry reduces the impact on the environment during synthesis 136-90-3, name is 4-Methoxy-3-methylphenylamine, I believe this compound will play a more active role in future production and life.

Compound 107 3-[[(3S)-tetrahydrofuran-3-yl]sulfamoyl]benzoic acid (270 mg, 1.0 mmol) was dissolved in dichloromethane (5 mL). 3-methyl-4-methoxyaniline (165 mg, 1.2 mmol) and triethylamine (145 mg, 1.4 mmol) were added to the mixture at 20C. The mixture was stirred at 20C for 5 minutes. HATU (456 mg, 1.2 mol) was added and the mixture was further stirred at 20C for 8 hours. The solvent was removed in vacuo and the obtained residue was purified by high performance liquid chromatography (Column: Phenomenex Synergi C18 150*20mm*5um.. A: H2O+0.1%TFA B: MeCN from 30% to 60 % B in A). The product fractions were collected and the organic solvent was evaporated in vacuo. The aqueous layer was neutralized with saturated aqueous NaHCC>3 and extracted with dichloromethane (2 x 10 mL). The combine organic layers was dried over Na2S04 and concentrated in vacuo resulting in compound 107 (135 mg). Method A; Rt: 5.24 min. m/z : 391.3 (M+H)+ Exact mass: 390.1

The chemical industry reduces the impact on the environment during synthesis 4-Methoxy-3-methylphenylamine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; JANSSEN R&D IRELAND; LAST, Stefaan Julien; RABOISSON, Pierre Jean-Marie Bernard; ROMBOUTS, Geert; VANDYCK, Koen; VERSCHUEREN, Wim Gaston; WO2014/33170; (2014); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Some common heterocyclic compound, 366-99-4, name is 3-Fluoro-4-methoxyaniline, molecular formula is C7H8FNO, 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. 366-99-4

To 124 (1.09 g, 3.5 mmol) dissolved in acetone (25 mL) was added 3-fluoro- p-anisidine (0.54 g, 3.5 mmol) in acetone (5 mL) followed by addition of 2.5 N NaOH (1.4 mL, 3.5 mmol) and water (3.5mL). The reaction mixture was stirred and heated at reflux for 3 hours. The reaction mixture was extracted three times using dichloromethane ; the combined organic layers were washed with brine and dried over potassium carbonate. The sample was filtered, concentrated in vacuo, and the resulting solid was dried overnight under vacuum to yield white solid (E15) (1.332 g,97percent) ; mp194 C ; HPLC: Inertsil ODS 3V C18,40 : 30: 30 v: v: v[KH2P04(0. 01 M, pH 3.2) : CH30H: CH3CN], 264nm,Rt 33.2 min, 97.6percent purity; MS (TOF ES+)mlz 396 (35.0) ; 394 (M+H, 100).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 366-99-4, its application will become more common.

Reference:
Patent; REDDY US THERAPEUTICS, INC.; WO2004/26844; (2004); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

1462-37-9, name is ((2-Bromoethoxy)methyl)benzene, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. 1462-37-9

To a stirred solution of 3,5-dimethyl lH-pyrazole-3,5-dicarboxylate (10 g, 54.30 mmol, 1 equiv.) and [(2-bromoethoxy)methyl] benzene (12.8 g, 59.51 mmol, 1.096 equiv.) in MeCN (200 mL) was added K2CO3 (11.3 g, 81.46 mmol, 1.5 equiv.) at room temperature under nitrogen atmosphere. The resulting mixture was stirred for 4 h at 90 ¡ãC. The mixture was allowed to cool down to room temperature and then quenched with water. The resulting mixture was extracted with EtOAc and the combined organic layers were dried over anhydrous Na2S04. After filtration, the filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography, eluting with PE/EtOAc (10: 1) to afford the title compound as a yellow oil in 96.22percent yield.

Statistics shows that 1462-37-9 is playing an increasingly important role. we look forward to future research findings about ((2-Bromoethoxy)methyl)benzene.

Reference:
Patent; IDEAYA BIOSCIENCES, INC.; ALAM, Muzaffar; BECK, Hilary Plake; DILLON, Michael Patrick; GONZALEZ-LOPEZ, Marcos; RICO, Alice Chen; SUTTON, JR., James Clifford; (317 pag.)WO2019/18562; (2019); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

A common compound: 2752-17-2, name is 2,2′-Oxydiethanamine, belongs to ethers-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 2752-17-2

For the synthesis of H2L, salicylic aldehyde (10 mM, 1.22 g) in EtOH (5 mL) was added dropwise to 5mL of an EtOH solution of 3-oxapentane-1,5-diamine (5 mM, 0.52 g). After completion of addition, the solution was stirred for an additional 4 h at 78 C. After cooling to room temperature, the precipitate was filtered. The product was dried in vacuo, giving a yellow crystalline solid. Yield: 1.19 g (68.5%).

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, 2752-17-2, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Wu, Huilu; Pan, Guolong; Bai, Yuchen; Wang, Hua; Kong, Jin; Shi, Furong; Zhang, Yanhui; Wang, Xiaoli; Journal of Coordination Chemistry; vol. 66; 15; (2013); p. 2634 – 2646;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 1535-75-7, name is 2-(Trifluoromethoxy)aniline, A new synthetic method of this compound is introduced below., 1535-75-7

General procedure: The benzoic acid 1 (1.50 g, 7.46 mmol) was refluxed in neat thionyl chloride (2 mL) for 2 h then allowed to cool to rt. The excess thionyl chloride was removed under reduced pressure to yield the crude acid chloride. A solution of anilines in DCM (10 mL) was added to a solution of the crude acid chloride in DCM (10 mL), followed by triethylamine (2.25 mL). The mixture was stirred at room temperature under argon for 3 h, after which the solvent was removed. The residue was purified by recrystallization (petroleum ether- ethyl acetate) to afford the product.

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; Liu, Fang; Venter, Henrietta; Bi, Fangchao; Semple, Susan J.; Liu, Jingru; Jin, Chaobin; Ma, Shutao; Bioorganic and Medicinal Chemistry Letters; vol. 27; 15; (2017); p. 3399 – 3402;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

588-96-5, name is p-Bromophenetole, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. 588-96-5

General procedure: The Teflon-lined sealed tube (20 mL) was charged with a 1,4-dioxane solution of sodium fluoroalkoxide RFONa [freshly prepared from fluoroalkanol RFOH (3.3(n + 1) mmol) and Na (3.0 (n + 1) mmol) in 1,4-dioxane (5 mL)], unactivated arylbromide ArBrn (3.0 mmol), CuBr (0.3n mmol) and DMF (3.0n mmol). The sealed tube was heated to 110 C and stirred for 6 h. After the completion of reaction, the concentration of the mixture in vacuo gave a residue, to which was added methyl tert-butyl ether (MTBE, 20 mL) and diluted hydrochloric acid (10 mL, 1.0 mol/L). The organic phase was separated, and the aqueous phase was extracted with MTBE (10 mL 9 3). The combined organic layer was dried over anhydrous MgSO4, andthen concentrated in vacuo to supply a crude product. Lastly, the purification of the crude product provided the desired product via column chromatography on silica gel (eluents: petroleum ether/ethyl acetate 20:1).

Statistics shows that 588-96-5 is playing an increasingly important role. we look forward to future research findings about p-Bromophenetole.

Reference:
Article; Guo, Ying; Li, Yu-Dao; Chen, Cheng; Zhao, Jian-Hong; Liu, Hong-Wei; Liao, Dao-Hua; Ji, Ya-Fei; Research on Chemical Intermediates; vol. 42; 3; (2016); p. 2525 – 2537;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

3401-47-6,Some common heterocyclic compound, 3401-47-6, name is 1-Bromo-2-methoxynaphthalene, molecular formula is C11H9BrO, 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.

237 g of 1-bromo-2-methoxynaphthalene (1 mol) and 200 ml of toluene were added to a 2000 ml reaction flask, and water was refluxed at 110 C. After the water was separated, 1000 ml of THF was added to the reaction flask under N 2 protection.Add 344g of triisopropyl borate (liquid, 1.8mol) dropwise (addition time is 30 minutes), cool down to -65 ~ -60 C, and add dropwise (addition time is 60 minutes)450 ml of n-butyllithium (1.125 mol), reacted at -65 to -60 C for 20 minutes; at this time, it was monitored by HPLC.1-Bromo-2-methoxynaphthalene is less than 5%, 2-methoxynaphthalene-1-boronic acid content is greater than 77%,250 ml of 5% hydrochloric acid solution was added to the reaction solution, the reaction was quenched, the layer was static, and the upper layer was an organic layer. The organic layer was washed once with water (500 ml of water), and the layer was statically layered, and the organic layer was taken at 55-65 C. At -0.05 Mpa, the solvent was decompressed under reduced pressure to 10% of the original volume (in a slurry state), and 400 ml of DCM was added thereto, stirred uniformly, and then vacuum filtered at -0.05 Mpa, and the filter cake was dried at a constant pressure of 50 C to a constant weight. White powder2-methoxynaphthalene-1-boronic acid 120 g (0.594 mol), content 99.2%; yield: 58.9%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3401-47-6, its application will become more common.

Reference:
Patent; Silver Pounuo New Materials Co., Ltd.; Li Xianyue; Song Wenzhi; Wu Qinglai; Guo Lei; Fu Chunrong; Yu Peng; (8 pag.)CN109305981; (2019); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem