Category: ethers-buliding-blocks

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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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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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., COA of Formula: C10H10O2

Formula 7 of the azide compound (300 mumol), alkynyl (750 mumol), CuSO4 (9.6 mg, 60 mumol) and Na. An ascorbate (60.0 mg, 300 mumol) 1: was dissolved in 1 t-BuOH / H2O (3 mL). The mixture was stirred at room temperature for 2 hours. After the reaction was completed, the mixture was filtered of and washed using H2O (70 mL) (solid A). The filtrate was extracted with EtOAc (3 × 70 mL). The combined organic extracts were then dried using anhydrous MgSO4, filtered and concentrated by rotaryevaporation (residue B). It was combined and the solid residue A and B, was purified by column chromatography to give the compound of formula 2 and 3. Following the general method for the general formula 2, 1: 1 t-BuOH / H2O (1 mL) Compound 7g (31.2 mg, 100 mumol), in a 1-Ethynyl -3,5-dimethoxy-benzene (40.5 mg, 250 mumol), CuSO4 (3.2 mg, 20 mumol) and Na. Using ascorbate (20.0 mg, 100mumol) was prepared the desired compound. After stirring at 60 the reaction mixture for 5 hours, was purified by column chromatography (5: 1 hexane / EtOAc ? 20: 1 CH2Cl2 / MeOH) using afford 2g as a brown solid (33,6mg, 71% ).

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; EWHA UNIVERSITY INDUSTRY-ACADEMIC COOPERATION FOUNDATION; YOO, JAE SANG; SONG, DOO HUI; (33 pag.)KR2015/134731; (2015); A;,
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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. 1077-01-6, name is 1-Fluoro-3-(trifluoromethoxy)benzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 1-Fluoro-3-(trifluoromethoxy)benzene

(Comparative Example 6); 4-Fluoro-l-nitro-2- (trifluoromethoxy) benzeneFuming nitric acid (20 mL) was added dropwise to concentrated sulfuric acid (40 ml) under cooling (-100C), and subsequently, 1- fluoro-3- (trifluoromethoxy) benzene (15 g, 83 mmol) was added to the mixture at -100C, and the mixture was stirred for 0.5 hours. After the mixture was added into ice-water to stop the reaction, it was extracted with dichloromethane . After the obtained organic layer was washed with a IN aqueous sodium hydroxide solution and water, it was dried with anhydrous sodium sulfate. After filtration, the solution was concentrated and the residue was purified by silica gel column chromatography (100:0-97:3, hexane : ethyl acetate) to give the title compound (3.1 g, 16%) as an oil.1H-NMR (400 MHz, CDCl3) delta: 8.10 (IH, dd, J = 5.5, 9.4 Hz) , 7.23-7.15 (2H, m) .

The synthetic route of 1077-01-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EXELIXIS, INC.; Daiichi Sankyo Company, Limited; NUSS, John; WILLIAMS, Matthew; MOHAN, Raju; MARTIN, Richard; WANG, Tie-lin; TSURUOKA, Hiroyuki; AOKI, Kazumasa; HONZUMI, Masatoshi; ASOH, Yusuke; SAITO, Keiji; HOMMA, Tsuyoshi; WO2010/42626; (2010); A1;,
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These common heterocyclic compound, 886762-08-9, name is 5-Bromo-2-(trifluoromethoxy)aniline, 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. Recommanded Product: 5-Bromo-2-(trifluoromethoxy)aniline

General procedure: To a solution of N-tosylhydrazone (0.6mmol, 1.1 eq) in distilled dioxane (8mL) was added bis(acetonitrile)palladium(II) chloride (0.05mmol, 5mol %), and dppp (0.1mmol, 10mol %). The resulting suspension was stirred RT for 2min, and cesium carbonate (1.5mmol, 3.0 eq) was added. Then, the reaction mixture was stirred for additional 2min, and aryl bromide (0.5mmol, 1.0 eq) was added in one portion. The mixture was then heated at 100C for 3h. The crude reaction mixture was allowed to cool to rt. EtOAc was added, and the mixture was filtrated through Celite. The solvent was evaporated under reduced pressure, and the crude product was purified by flash chromatography on silica gel.

The synthetic route of 5-Bromo-2-(trifluoromethoxy)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Article; Naret, Timothee; Bignon, Jerome; Bernadat, Guillaume; Benchekroun, Mohamed; Levaique, Helene; Lenoir, Christine; Dubois, Joelle; Pruvost, Alain; Saller, Francois; Borgel, Delphine; Manoury, Boris; Leblais, Veronique; Darrigrand, Romain; Apcher, Sebastien; Brion, Jean-Daniel; Schmitt, Etienne; Leroux, Frederic R.; Alami, Mouad; Hamze, Abdallah; European Journal of Medicinal Chemistry; vol. 143; (2018); p. 473 – 490;,
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Application of 592-55-2, 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. 592-55-2 name is 1-Bromo-2-ethoxyethane, 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.

To A solution of 1- (3-Methoxy-4-nitro-phenyl)-piperidin-4-ol (300mg, 1. 2 mmol) in N, N- dimethylformamide (3.0 mL), sodium hydride (1.52g, 3.8 MMOL) is added. After stirring, 2- bromethyl methyl ether (1501L1, 1.6 MMOL) is added and the mixture is further stirred at 70C for 15 hours. After addition of saturated aqueous ammonium chloride, the mixture is poured into water and extracted twice with ethyl acetate. The organic layer is washed with brine, dried over sodium sulfate, and evaporated in vacuo. The residue is purified by silica gel column chromatography (n-hexane-ethyl acetate gradient) to afford 4- (2-METHOXY-ETHOXY)-1- (3- METHOXY-4-NITRO-PHENYL)-PIPERIDINE (111 MG, 29%) as a yellow oil. ‘H-NMR (400MHZ, CDCI3, O, ppm): 1.52 (t, 3H), 1.95-2. 00 (m, 2H), 1.70-1. 79 (m, 2H), 3.23 (ddd, 2H), 3.58-3. 64 (m, 2H), 3.65-3. 68 (m, 2H), 3.64-3. 72 (m, 2H), 3.95 (s, 3H), 6.31 (d, 1H), 6.42 (dd, 1 H), 8.00 (d, 1 H). RF 0. 53 (n-hexane: AcOEt=1 : 1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-2-ethoxyethane, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2004/80980; (2004); A1;,
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Synthetic Route of 38336-04-8, 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. 38336-04-8 name is 2-(Benzyloxy)-1-ethanamine, 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.

To a stirred solution of 16 (2.30 g, 7.20mmol) in toluene (45 mL) were added 2-phenylmethoxyethanamine 1717 (1.24 g, 8.19 mmol), sodiumtert-butoxide (2.09 g, 21.7 mmol), Pd2(dba)3 (336 mg, 0.367 mmol), and (S)-BINAP (547 mg, 0.879mmol). After stirring at 80 C for 19 h, the reaction mixture was cooled to room temperature and thendiluted with Et2O (20 mL). The mixture was filtered through a Celite pad and the residue was washedwith Et2O for several times. The combined filtrate was concentrated under reduced pressure, and theresidue was purified by flash silica gel column chromatography (hexane/EtOAc = 30/1) to afford 19 (2.06g, 73%) as a white solid: Rf = 0.50 (hexane/EtOAc = 10/1); 1H NMR (400 MHz, CDCl3) delta 7.43-7.27 (m,10H), 6.79-6.68 (m, 3H), 5.06 (s, 2H), 4.55 (s, 2H), 3.74 (t, J = 5.5 Hz, 2H), 3.40 (t, J = 5.5 Hz, 2H), 1.29(s, 9H); 13C NMR (125 MHz, CDCl3) delta 144.5, 144.4, 138.3, 137.8, 137.5, 128.6, 128.5, 127.9, 127.7,127.6, 113.2, 110.7, 108.3, 73.1, 70.6, 68.8, 43.7, 34.4, 31.7 ppm; IR (ATR) numax: 3386, 3063, 2966, 2859,1604, 1451, 1391, 1213, 1035, 695, 650 cm-1; HRMS (ESI) [M+H+] calcd for C26H32NO2: 390.2428,found 390.2419; mp 56.7 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(Benzyloxy)-1-ethanamine, and friends who are interested can also refer to it.

Reference:
Article; Matsumoto, Yuri; Nakamura, Akihiko; Saito, Emi; Nakada, Masahisa; Heterocycles; vol. 97; 1; (2018); p. 232 – 252;,
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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. 588-63-6, name is (3-Bromopropoxy)benzene, A new synthetic method of this compound is introduced below., Computed Properties of C9H11BrO

2,4-diamino-5-hydroxy -1, 3, 5-tri-aza-9-oxa-spiro [5.5] undecane -1,3-diene-hydrochloride (0.47g, 0 . 002mol), sodium hydroxide (0.08g, 0 . 002mol), methanol 10 ml in mixed in the round-bottom flask, heating to reflux 30 minutes, the heat filters, concentrating the filtrate. By adding 1-bromo-3-phenoxy-propane (0.52g, 0 . 0024mol) and DMF2ml, stirring the mixture at room temperature. When consumes TLC monitoring raw materials, into a small amount of thick hydrogen PH value in order to adjust the bromate 2-3. Remove the solvent under reduced pressure, to obtain white solid, with ethanol: water = 10:1 ( volume ratio ) recrystallization, get white crystal 0.26g, yield 31.7percent, HPLC purity measured 99.6percent.

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; Shanghai Institute Of Pharmaceutical Industry(China State Institute of Pharmaceutical Industry); zhou, xiaotian; lin, kuaile; zhou, Weicheng; (41 pag.)CN103664972; (2016); B;,
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Application of 62257-15-2, 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 62257-15-2 as follows.

To a mixture of 2-fluoro-5-methoxyaniline (5.0 g, 35 rnmol), sulfuric acid (7.5 niL), trifluoroacetic acid (37.5 mL) and water (45 mL) was added NaNO2 (3.7 g, 53 mmoi)portionwise at 0 C. The mixture was stirred for 30 mm at 0 C and NaN3 (4.6 g, 71 mmol) was added. The resulting solution was stirred overnight at RT and extracted with EtOAc (2 x 200 mL), The combined organic layers were dried over Na2SO4 and concentrated. The residue obtained was purified by column chromatography on silica gel (EtOAc/petroleum ether, 1100) to give compound 5a as a light yellow oil. ?H-NMR (300MHz, DMSO-d6) d (ppm): 723 (dd, Ji = 9.0 Hz, J2= 10.8 Hz. 1H), 6.72 – 6.80 (m, 2H),3.76 (s, 3H). Mass Spectrum (GCMS. Efl: Calcd. ?for C7H6FN3O: 167.0 (M); found: 167.2

According to the analysis of related databases, 62257-15-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; HUANG, Hui; MEEGALLA, Sanath; PLAYER, Mark R.; (212 pag.)WO2017/27312; (2017); A1;,
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Reference of 53087-13-1, These common heterocyclic compound, 53087-13-1, name is 1-(Benzyloxy)-3-bromobenzene, 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.

Step3. 4-(4-morpholinyl)-1-{3-[(phenylmethyl) oxy] phenyl}-1-butanone Under argon, to a solution of 1-bromo-3-[(phenylmethyl) oxy] benzene (2.04 g, 7.76 mmol) in THF (30 mL) at-78 C, was added dropwise n-BuLi (5.1 mL, 1.6 M in Hexanes), 20 min after the addition, this solution was added to a solution the product from Step 3 (1.68 g, 7.76 mmol) in THF (30 mL) under argon at-78 C. 15 min later, the reaction mixture was slowly warmed to 0 C. The reaction mixture was poured into a mixture of EtOAC and NH4C1, then extracted with EtOAC (2X), organic layers were combined, washed with brine, dried over Na2SO4, filtered and concentrated. The residue was then purified with flash chromatography (hexanes/ethyl acetate 1: 4), to afford the title compound as a colorless oil (932 mg, 35%).

The synthetic route of 53087-13-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2005/37197; (2005); A2;,
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