Month: July 2021

Application of 1663-61-2,Some common heterocyclic compound, 1663-61-2, name is (Triethoxymethyl)benzene, molecular formula is C13H20O3, 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-1: To a stirred solution of methyl 2-oxo-2,3-dihydro-1H-pyrrolo[3,2-b]pyridine-6-carboxylate (0.18 g, 0.9366 mmol) in acetic anhydride (4 ml) was added triethyl orthobenzoate (0.630 g, 2.8098 mmol) at RT and the mixture was refluxed for 3 h at 110° C. The reaction mixture was evaporated and the resulting residue was used as such into next step without purification. [0212] Step-2: To a stirred solution of product from step-1 (0.18 g) in DMF (4 ml) was added N-(4-aminophenyl)-N-methyl-2-(4-methylpiperazin-1-yl)acetamide (0.180 g, 0.6861 mmol) at RT and the reaction mixture was heated at 110° C. for 1 h. The reaction mixture was cooled to RT and stirred with triethyl amine (1 ml) for half an hour. The reaction mixture was evaporated and the crude product was purified by column chromatography using 0 to 10percent methanol in dichloromethane as eluent to afford (Z)-methyl 1-acetyl-3-((4-(N-methyl-2-(4-methylpiperazin-1-yl) acetamido)phenylamino)(phenyl)methylene)-2-oxo-2,3-dihydro-1H-pyrrolo[3,2-b]pyridine-6-carboxylate as yellow solid. MS (ES+): m/z 583.4 (MH+).

The synthetic route of 1663-61-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ANGION BIOMEDICA CORP.; NARAYAN, Prakash; HUANG, Brian; PAKA, Prani; PAKA, Latha; GOLDBERG, Itzhak D.; US2015/105380; (2015); A1;,
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Application of 175278-17-8, 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. 175278-17-8 name is 2-Bromo-4-(trifluoromethoxy)aniline, 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.

A solution of commercially available 2-bromo-4-(trifluoromethoxy)aniline (theproduct of step 1, Example 55, 4.00 g, 15.63 mmol) in DMF (1 0 mL) was addedslowly to a suspension of NaH (60% in mineral oil, 1.13 g, 46.88 mmol) in DMF(20 mL) at 0C. After warming to room temperature the reaction mixture wasstirred for 30 minutes. Commercially available tert-butyl 4-(chloromethyl)-5,6-dihydropyridine-1 (2H)-carboxylate (3.62 g, 15.63 mmol) in DMF (1 0 mL) was added and the mixture stirred at room temperature for 1 hour. Cold water (100 mL) was added and the mixture extracted with ethyl acetate (3 x 100 mL). The combined organic layers were washed with cold water (2 x 50 mL) and brine(5OmL), dried over anhydrous sodium sulphate and concentrated. The crudematerial was purified by flash chromatography eluting with 20% ethylacetate/hexane to afford the title compound as grey solid (2.5 g, 36%): 1 H NMR(400 MHz, DMSO-d6) oe: 1 .38 (5, 9 H), 1 .99 (bs, 2 H), 3.39 (t, 2 H), 3.75 (bs, 4 H),5.50 (5, 1 H), 5.79 (t, 1 H), 6.60 (d, 1 H), 7.17 (d, 1 H), 7.47 (d, 1 H). LC-Ms(m/z): [M-H] = 448.8.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-4-(trifluoromethoxy)aniline, and friends who are interested can also refer to it.

Reference:
Patent; ZOETIS SERVICES LLC; WENDT, John; COX, Mark; SHEEHAN, Susan, M.k.; CURTIS, Michael, P.; RESPONDEK, Tomasz; EWIN, Richard, Andrew; KYNE, Graham, M.; JOHNSON, Paul, D.; WO2015/100232; (2015); A2;,
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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. 36449-75-9, name is 1-(2-Bromoethyl)-2-methoxybenzene, A new synthetic method of this compound is introduced below., Recommanded Product: 1-(2-Bromoethyl)-2-methoxybenzene

Compound 1. 1 -(2-methoxyphenethyl)-4-phenethylpiperidine A 250 mL round bottom flask was equipped with a magnetic stir bar, and then charged with 5 grams (0.0537 mol) of 4-picoline, 6.84 grams (0.0644 mol) of benzaldehyde, and 50 mL of acetic anhydride. The reaction mass was heated to reflux and maintained at that temperature for 72 hours. The reaction mixture was then cooled to room temperature, and subjected to silica chromatography. Yield of (E)-4-styrylpyridine was 5.2 grams (53%). The 5.2 grams of (E)-4-styrylpyridine was then charged into a 500 ml hydrogenation flask, to which was added 50 mL of acetic acid as well as 43 mg of Pt02. The reaction mass was subjected to 45 psi of hydrogen gas, and allowed to react at room temperature for 16 hours. The reaction mixture was then filtered through a pad of celite, evaporated, basified with aqueous Na2C03 solution, and extracted with dichloromethane. The combined extraction solvents were removed under reduced pressure via rotovap. The residue was then subjected to silica chromatography, yielding 4.6 grams (78.4% yield) of 4-phenethylpiperidine. A 100 mL round bottomed flask equipped with a magnetic stir bar was then charged with 2.0 grams of 4-phenethylpiperidine (0.0106 mol), 2.5 grams of 2-methoxyphenethylbromide (0.0127 mol), 3.65 grams of K2C03 (0.0264 mol), and 25 mL of DMF as solvent. The reaction mass was then heated to 70 C for 24 hours. The excess DMF was removed via reduced pressure, partitioned with water and dichloromethane, the organic layer separated; excess solvent removed under reduced pressure and the residue was subjected to silica chromatography. Yield of 1 -(2-methoxyphenethyl)-4-phenethylpiperidine was 2.14 grams (62.3% yield). NMR (300 MHz, CDC13) delta 1.31 -1.63 (m, 7H), 2.32-2.85 (m, 10H), 3.87 (s, 3H), 6.83-7.35 (m, 9H) ppm.

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; UNIVERSITY OF KENTUCKY RESEARCH FOUNDATION; CROOKS, Peter, A.; DWOSKIN, Linda, P.; CULVER, John; NICKELL, Justin, R.; ZHENG, Guangrong; WO2014/144064; (2014); A2;,
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Synthetic Route of 89521-55-1, 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 89521-55-1 as follows.

EXAMPLE 27; Ethyl[8-(benzyloxy)-3-oxo-3,4-dihydroquinoxaline-2(1H)-ylidene]acetate 60a; To 3-(benzyloxy)benzene-1,2-diamine (300 mg, 1.4 mmol) in solution in 2 ml of acetic acid, add diethyloxalacetate sodium salt (295 mg, 1.4 mmol) and stir under reflux for 2 hours. Evaporate to dryness and chromatograph to obtain the abovenamed product. Yield: 20%. 1H-NMR (200 MHz, DMSO-d6): delta 11.39 (broad s, 1H, NH), 8.70 (broad s, 1H, NH), 7.53-7.37 (m, 5H arom.), 6.93-6.84 (t, 1H, J=8 Hz, 1H arom.), 6.71-6.67 (d, 1H, J=8 Hz, 1H arom.), 6.57-6.53 (d, 1H, J=8 Hz, 1H arom.), 5.84 (s, 1H, CCH), 5.29 (s, 1H, OCH2-Ph), 4.30-4.20 (q, 2H, J=7 Hz, OCH2-CH3), 1.35-1.28 (t, 3H, J=7 Hz, OCH2CH3).

According to the analysis of related databases, 89521-55-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Schmitt, Martine; Klotz, Evelyne; Macher, Jean-Paul; Bourguignon, Jean-Jacques; Abarghaz, Mustapha; Wagner, Patrick; Ronsin, Gael; US2006/183909; (2006); 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 10103-06-7 as follows. Application In Synthesis of 2,3-Dimethoxynaphthalene

EXAMPLE 9 2-(4-Chlorobutyl)-6,7-dimethoxynaphthalene Aluminum chloride (25.5 g, 0.19 mole) was added to a solution of 21.5 mL (0.19 mole) of 4-chlorobutyryl chloride in 225 mL of methylene chloride. To the resulting solution, cooled in an ice bath, was added dropwise a solution of 30.0 g (0.16 mole) of 2,3-dimethoxynaphthalene in 150 mL of methylene chloride over 30 minutes. The reaction mixture was stirred at 3 C. for 30 minutes and at 24 C. for 17 hours. The reaction mixture was worked up as Example 5 and the crude product was recrystallized from acetone-hexane, to give 31.5 g (68% yield), mp 98-99, of 4-chloro-1-(6,7-dimethoxy-2-naphthalenyl)-1-butanone. Anal Calcd. for C16 H17 ClO3: C, 65.64; H, 5.85; Cl, 12.11. Found: C, 65.33; H, 5.77; Cl, 12.16.

According to the analysis of related databases, 10103-06-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hoffmann-La Roche Inc.; US4937371; (1990); A;,
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Related Products of 876-32-4,Some common heterocyclic compound, 876-32-4, name is 4-Methoxy-N-methylbenzylamine hydrochloride, molecular formula is C9H14ClNO, 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.

In a sealed tube, mixture of benzamide 24b (38 mg, 0.11 mmol), formaldehyde (37% in water, 0.043 mL, 0.55 mmol), 1-(4-methoxyphenyl)-N-methylmethanamine hydrochloride (102 mg, 0.55 mmol), and 1N NaOH (0.5 mL) in H2O:THF (1 mL:0.5 mL) was heated at 65 C for 2 hours. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate, washed with brine, dried over Na2SO4, and concentrated, then purified by column chromatography to afford the pure product (28 mg, 57% yield) as off white solid. 1H NMR (CDCl3, 300 MHz) delta: 7.73 (d, J= 1.8 Hz, 1H), 7.49 (d, J= 8.7 Hz, 1H), 7.36 (dd, J= 1.8, 8.7 Hz, 1H), 7.23 (d, J= 8.7 Hz, 2H), 7.20- 7.13 (m, 1H), 6.91-6.84 (m, 1H), 6.85 (d, J= 8.7 Hz, 2H), 6.17 (bs, 1H), 5.35 (s, 2H), 4.38 (d, J= 6.3 Hz, 2H), 3.79 (s, 3H), 3.59 (s, 2H), 2.32 (s, 3H).

The synthetic route of 876-32-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY; UNIVERSITY OF MEDICINE AND DENTISTRY OF NEW JERSEY; LAVOIE, Edmond J.; PARHI, Ajit; ZHANG, Yongzheng; PILCH, Daniel S.; KAUL, Malvika; WO2013/142712; (2013); A1;,
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These common heterocyclic compound, 64465-53-8, name is 4-Fluoro-3-methoxyaniline, 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. name: 4-Fluoro-3-methoxyaniline

INTERMEDIATE PREPARATION 145-a nolTo a solution of 4-fluoro-3-(methyloxy)aniline (3.8 g, 26.92 mmol) in methylene chloride (50 mL) at 0C was added boron tribromide (20.2 g, 80.77 mmol). The mixture was quenched with methanol and concentrated in vacuo. The residue was dissolved in methanol and reconcentrated two times. The residue was dissolved in water and NaHC03 was added. The resulting solution was extracted with ethyl acetate, washed with brine, dried over MgS04, filtered and concentrated to afford 5-amino-2-fluorophenol (3.0 g).

The synthetic route of 4-Fluoro-3-methoxyaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE LLC; BROOKS, Carl, A.; CHEUNG, Mui; EIDAM, Hilary, S.; FOX, Ryan, M; HILFKER, Mark, A.; MANAS, Eric, S.; YE, Guosen; WO2011/119704; (2011); A1;,
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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. 103-50-4, name is Benzyl ether belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C14H14O

General procedure: In the mixture of cyclic/acyclic ether (11 mmol) and acid chloride (10 mmol), nano-ZnO (5 mol%) was added at 0-5 C and stirred at room temperature for an appropriate time. After the TLC monitoring reaction, the ZnO was removed by filtration and washed repeatedly with dichloromethane and water. It was then dried at 60 C for 3 h and used for the next catalytic cycle. The solution was extracted three times with dichloromethane and water, and dried on anhydrous Na2SO4. The product was purified on a silica gel column chromatography using a mixture of petroleum ether/ethyl acetate (150:1, v/v). The product is obtained by vacuum distillation to remove the solvent. The compounds were characterized by 1H NMR and 13C NMR.

The synthetic route of 103-50-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chen, Junqing; Feng, Chengliang; Ji, Min; Tang, Yuqi; Wang, Wei; Yang, Wanfeng; Chemical Papers; (2020);,
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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. 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 1-Bromo-2-(2-bromoethoxy)ethane

To a stirred solution of 3-amino-1-bromoisoquinoline (444 mg, 2.00 mmol) in anhydrous dimethylformamide (10 mL) was added sodium hydride (60%, unwashed, 96 mg, 2.4 mmol) in one portion. The mixture was stirred at 25 C. for 5 min before 2-bromoethyl ether (90%, 250 muL, 2.00 mmol) was added. The mixture was stirred further at 25 C. for 5 h and at 75 C. for 72 h before it was cooled to 25 C., quenched with saturated ammonium chloride solution and diluted with ethyl acetate. The organic layer was separated, washed with water and brine, dried over 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-WI); 90% homogenity index; LCMS: Anal. Calc. for [M+H]+ C13H4BrN2O: 293.03; found: 293.04.

According to the analysis of related databases, 5414-19-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bristol-Myers Squibb Company; US2009/233925; (2009); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 101-55-3, A common heterocyclic compound, 101-55-3, name is 1-Bromo-4-phenoxybenzene, molecular formula is C12H9BrO, 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.

General procedure: Suzuki-coupling reaction was carried out in a 25mL round bottom (RB) flask. Initially, RB was cleaned with water and then rinsed with acetone followed by drying at 60C in an oven for one hour. One mmol of bromobenzene and two mmol of phenylboronic acid were poured into RB. Subsequently, 2mL of toluene was inserted into the RB and closed with a rubber septum. The reaction solution was purged with N2 gas for 30min for the complete removal of air from the mixture. After that, RB was charged with 30mg of Ag/TiO2 photocatalyst, and the vessel was sealed with the rubber septum. The reaction mixture again purged with the N2 gas for the residual air and then irradiated with the 20W white LED (lambda ~ 420nm) for 24h. The sample was analyzed with TLC after every two-hour interval. The conversion and the yield were determined with GC-FID (Thermo equipped with Stabilwax w/Integra- Guard 30-m-long column), and confirmation was obtained by the 1H and 13C NMR of the pure samples.

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; Chen, Yuning; Feng, Li; Journal of Photochemistry and Photobiology B: Biology; vol. 205; (2020);,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem