Month: November 2020

Adding a certain compound to certain chemical reactions, such as: 103291-07-2, name is 4-Bromo-1-fluoro-2-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 103291-07-2, 103291-07-2

To a solution of 69A (2.7 g, 13.1 mmol) in THF (25 mL) at -78 C. was added n-BuLi (1.6 M in hexanes, 11.0 mL, 17.7 mmol). The mixture was stirred at -78 C. for 40 min before trimethyl borate (2.7 mL, 24.3 mmol) was added. The reaction was left stirring from -78 C. to rt over 18 h. It was quenched with 1.0 N HCl (40 mL), extracted with EtOAc, washed with brine and dried over Na2SO4. After evaporation of the solvent, the crude solid product was triturated with EtOAc/hexanes (1:4). After filtration, 69B (0.75 g, 35% yield) was collected as a white solid. 1H NMR (400 MHz, Methanol-d4) delta ppm 3.86 (s, 3 H) 7.03-7.45 (m, 3 H).

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, 4-Bromo-1-fluoro-2-methoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bristol-Myers Squibb Company; US2007/3539; (2007); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

A common compound: 115144-40-6, name is 3,4-Difluoroanisole, 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. 115144-40-6

a) 7.29 ml (66.3 mmol) of titanium tetrachloride were added while stirring to a solution, cooled to 0, of 5.73 g (39.8 mmol) of 3,4-difluoroanisole in 30 ml of anhydrous dichloromethane. Subsequently, the mixture was treated dropwise over 10 minutes with 3.51 ml (39.6 mmol) of 1,1-dichloromethyl methyl ketone and stirred at room temperature for one hour. The mixture was poured into 100 ml of ice-water, extracted twice with 150 ml of dichloromethane each time and the combined organic phases were washed once with 100 ml of water and once with 100 ml of saturated sodium chloride solution. After drying over magnesium sulfate concentration was carried out in a vacuum. The crude product obtained was purified by column chromatography on silica gel (hexane/ethyl acetate 4:1). There were obtained 5.8 g (84%) of 4,5-difluoro-2-methoxybenzaldehyde as a white solid with m.p. 74.

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, 115144-40-6, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hoffmann-La Roche Inc.; US5955495; (1999); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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 54149-17-6 as follows. 54149-17-6

Under an argon atmosphere, bisimine 11 (3.0 g, 10.12 mmol, 1 eq.), 1-bromo-2-(2-methoxyethoxy) ethane (3.35 mL, 22.26 mmol, 2.2 eq.) of and K2CO3 (5.59 g, 40.48 mmol, 4 eq.) were dissolved in 150 mL of dry DMF in a vacuum dried Schlenk flask. The contents were heated at 100C for 24 hours and the reaction was cooled to room temperature and 200 mL of distilled water was added to it. This was then extracted with EtOAc (3¡Á200 mL) and washed with distilled water (300 mL) and with brine (200 mL). The organic layers were combined and dried over anhydrous Na2SO4 and concentrated in vacuuo to yield a brownish-yellow coloured paste. This paste was thoroughly washed with pentane (3¡Á20 mL) and dried to a yellow powder.

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; Shahane, Saurabh; Toupet, Loic; Fischmeister, Cedric; Bruneau, Christian; European Journal of Inorganic Chemistry; 1; (2013); p. 54 – 60;,
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20469-65-2, Name is 1-Bromo-3,5-dimethoxybenzene, 20469-65-2, 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.

Step 1: 5-bromobenzene-1,3-diol To a mixture of 1-bromo-3,5-dimethoxybenzene (15 g, 69.1 mmol) in dichloromethane (500 ml) at 0 00 was added BBr3 (14.37 ml, 152 mmol) dropwise over 5 minutes at 0 00. The reaction mixture was allowed to warm to room temperature andstirred for 5 hours. The reaction was then cooled to 0 00 and BBr3 (7.2 ml, 76 mmol) added dropwise. The reaction mixture was allowed to warm up to room temperature and stirred overnight. The reaction was again cooled to 0 00 and BBr3 (3.6 ml, 38 mmol) added dropwise. The reaction mixture was allowed to warm up to room temperature and stirred for 4 hours. The mixture was then poured slowly onto ice. When the ice melted,DCM (200 ml) was added and the layers separated. The aqueous was extracted with EtOAc (500 ml) and the layers separated. The combined organics were passed throughthrough a hydrophobic frit and concentrated. The residue was purified via flash chromatography (ISCO Combiflash Rf, 220 g column, 0-100 % ethyl acetate/hexanes) to give the title compound as a yellow oil (19.5 g, 70 % purity). MS (mlz) 189.0 (M).

Statistics shows that 1-Bromo-3,5-dimethoxybenzene is playing an increasingly important role. we look forward to future research findings about 20469-65-2.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; DOWDELL, Sarah E.; EIDAM, Hilary Schenck; ELBAN, Mark; FOX, Ryan Michael; HAMMOND, Marlys; HILFIKER, Mark A.; HOANG, Tram H.; KALLANDER, Lara S.; LAWHORN, Brian Griffin; MANNS, Sharada; PHILP, Joanne; WASHBURN, David G.; YE, Guosen; WO2015/104684; (2015); A1;,
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1163-19-5, The chemical industry reduces the impact on the environment during synthesis 1163-19-5, name is 6,6′-Oxybis(1,2,3,4,5-pentabromobenzene), I believe this compound will play a more active role in future production and life.

setupBDE209 stock solution (1 ¡Á 10-3mol/L) in tetrahydrofuran wasdiluted with methanol to 1 ¡Á 10-5mol/L. 0.05 mL pyruvic acidaqueous solution (1 ¡Á 10-2mol/L) was added to 10 mL BDE209methanol solution in a Pyrex vessel. Reaction solutions were mag-netically stirred during the irradiation. The Pyrex vessel was purgedwith argon for 30 min to remove O2and protected under argonatmosphere during the irradiation. A PLS-SXE300 Xe lamp (BeijingTrusttech Co. Ltd.) was used as the light source. To eliminate thedirect photolysis of BDE209, a cutoff filter was used to cut the irra-diation below 360 nm. To investigate the effect of acids/bases andH2O on the reaction kinetics, a given amount acid/base and H2Owere added under otherwise identical conditions. At given timeintervals, 1 mL aliquots were used for analysis.

The chemical industry reduces the impact on the environment during synthesis 6,6′-Oxybis(1,2,3,4,5-pentabromobenzene). I believe this compound will play a more active role in future production and life.

Reference:
Article; Jiang, Zhaowu; Linghu, Wensheng; Li, Yimin; Sun, Chunyan; Catalysis Today; vol. 224; (2014); p. 89 – 93;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 929-75-9 name is 1,11-Diamino-3,6,9-trioxaundecane, 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. 929-75-9

The compound 2-(4-(2-(4-(tert-butyl)-2-ethoxyphenyl)-4,5-bis(4-chlorophenyl)-4,5-dihydro-1H-imidazole-1-carbonyl)-2-oxo-piperazin-1-yl)acetic acid (25mg, 0.017mmol), HATU (14.45mg, 0.038mmol), DIPEA (6.1mg, 0.05mmol) was dissolved in dry DMF, the1,11-diamino-3,6,9-trioxaundecane (3.3 mg, 0.017 mmol) was slowly added dropwise to the above solution, and after reacting at room temperature for 1 h,The reaction was detected to be complete. The solvent was distilled off under reduced pressure and purified by silica gel column chromatography (eluent, dichloromethane / methanol = 100/3).18 mg of a pale yellow solid was obtained with a yield of 64.3%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,11-Diamino-3,6,9-trioxaundecane, and friends who are interested can also refer to it.

Reference:
Patent; Second Military Medical University; Sheng Chunquan; Dong Guoqiang; Ma Junhui; He Shipeng; Fang Yuxin; Wu Shanchao; Chen Shuqiang; (19 pag.)CN110563706; (2019); A;,
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A common compound: 702-24-9, name is 4-Methoxy-N-methylbenzylamine, 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. 702-24-9

A solution of amine (68 mg, 0.45 mmol) and IBX (252 mg, 0.90 mmol) in 10 mL of CHCl3 was heated at reflux with vigorous stirring for 6 h. The suspension was filtered and the filtrate was washed in sequence with 10percent NaOH (5 mL x 3), 1 M HCl (5 mL x 3), and water. The organic layer was dried with MgSO4 and concentrated in vacuo to afford the desired product (57 mg, 91percent yield). 1H NMR (400 MHz, 25 ¡ãC, CDCl3): delta = 9.89 (s, 1H), 7.85 (d, 2H, J = 8.0 Hz), 7.01 (d, 2H, J = 8.0 Hz), 3.90 (s, 3H) ppm. 13C NMR (100 MHz, 25 ¡ãC, CDCl3): delta = 190.89, 164.60, 132.01, 129.91, 114.31, 55.60 ppm. ESI?MS: M + Na+, found 159.1 (calc. 159.15).

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, 702-24-9, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Chen, Li-Xia; Huang, Yin-Hui; Cong, Hang; Tao, Zhu; Chemical Papers; vol. 72; 3; (2018); p. 661 – 667;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

22236-10-8, 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. 22236-10-8, name is 4-(Difluoromethoxy)aniline, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 51; 4-(6,7-Dimethoxy-quinazolin-4-yl)-piperidine-1-carboxylic acid (4-difluoromethoxy-phenyl)-amide; To a solution of 4-(6,7-dimethoxy-quinazolin-4-yl)-piperidine-1-carbonyl chloride (46.9 mg, 0.14 mmol), as prepared in Example 3a, in DMSO (1 mL) was added 4-(difluoromethoxy)aniline (26.6 mg, 0.17 mmol), followed by DIEA (35.9 mg, 0.28 mmol). The mixture was heated at 100 C. with stirring. After 2 h, it was cooled to room temperature and partitioned between EtOAc and water. The combined EtOAc extracts were dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (EtOAc?5% MeOH/EtOAc as eluent) to afford the title compound as a white solid (20.4 mg, 32%). 1H NMR (300 MHz, CDCl3) delta 9.09 (s, 1H), 7.40 (s, 1H), 7.38 (d, J=8.99 Hz, 2H), 7.27 (s, 1H), 7.07 (d, J=8.93 Hz, 2H), 6.48 (s, 1H), 6.45 (t, J=74.22 Hz, 1H), 4.28 (m, 2H), 4.08 (s, 3H), 4.07 (s, 3H), 3.62 (m, 1H), 3.20 (td, J=13.02 and 2.64 Hz, 2H), 2.14 (m, 2H), 2.01 (m, 2H). LC-MS (ESI) calcd mass 458.2, found 459.3 (MH+).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Baindur, Nand; Gaul, Michael David; Kreutter, Kevin Douglas; Baumann, Christian Andrew; Kim, Alexander J.; Xu, Guozhang; Tuman, Robert W.; Johnson, Dana L.; US2006/281772; (2006); A1;,
Ether – Wikipedia,
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The chemical industry reduces the impact on the environment during synthesis 366-99-4, name is 3-Fluoro-4-methoxyaniline, I believe this compound will play a more active role in future production and life. 366-99-4

Cyanuric chloride (1.84 g, 10 mmol) inCH3CN (20 mL) was cooled toabout-10 C was added3-fluoro-p-anisidine (1. 41 g, 10 mmol) followed by DIEA(1. 8 mL, 10 mmol). The reaction was stirred for about 45 min then at room temperature for about 45 min under an N2 atmosphere. Cycloheptylamine (1.26 mL, 10 mmol) was added followed by DIEA (1.8 mL, 10 mmol) and the reaction was stirred at room temperature overnight.N,N-dimethylethylenediamine (1. 1 mL, 10 mmol) was added followed by DIEA (1.8 mL, 10 mmol) and the mixture was heated at reflux under N2 overnight. The reaction was diluted with ethyl acetate, washed with brine, and dried over anhydrousK2C03. The material (1.178 g) was purified by silica gel column chromatography to afford a solid 150 (1.178 g,28percent), mp73-76 C ; HPLC: Inertsil ODS-3VC18, 40: 30: 30[KH2PO4 (O. 01M, pH 3.2) :CH30H :CH3CN], 264 nm,Rt 10.8 min, 95. 1percent purity ; MS (ESI):iiilz418 (M+H, 100), 373(11. 9), 322 (7.8), 277 (6.8), 162 (3.6).

The chemical industry reduces the impact on the environment during synthesis 366-99-4. I believe this compound will play a more active role in future production and life.

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

20781-20-8, 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 20781-20-8 as follows.

To a solution of 5-fluoro-2-nitrobenzoic acid (6.6g, 35.66 mmol) in dichloromethane (100 mL) were added DIPEA (9.22 g, 71.3 mmol), HOBt (6.0 g, 39.2 mmol) and EDCI (10.2 g, 53.5 mmol). After about 15 min stirring, to the reaction mixture was added a solution of 2,4-dimethoxybenzyl amine (5.96 g, 35.66 mmol) in dichloromethane (50 mL) dropwise under nitrogen atmosphere. The resulting mixture was stirred under nitrogen atmosphere at room temperature for 16 h. The reaction mixture was washed successively with IN HC1 (100 mL), sat. NaHC03 (100 mL) and brine (100 mL). The organic phase was then dried over MgS04. Filtration and solvent removal in vacuo afforded a yellowish solid, wt: 9.3g (78%). MS: [M+l] = 335.

According to the analysis of related databases, 20781-20-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AGENEBIO, INC.; MEKONNEN, Belew; BUTERA, John, A.; HUANG, Jianxing; WO2015/95783; (2015); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem