Month: July 2021

Adding a certain compound to certain chemical reactions, such as: 22483-09-6, name is 2,2-Dimethoxyethanamine, 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 22483-09-6, Safety of 2,2-Dimethoxyethanamine

General procedure: A solution of amino acetaldehyde dimethyl acetal 2a (10. 514 g, 1.081 mL, 10 mmol), purchased from Alfa Aesa, and an aldehyde (10 mmol) in dry ethanol was placed in a round bottom flask and stirred for 12 h. To that solution, sodium borohydride powder (0.567 g, 15 mmol) was added at 0 C slowly over 5 minutes. the solution was then warmed to room temperature. After stirring for 4 h, the reaction was quenched with 3 drops of water and the mixture was filtered through a pad of celite. The solvent was evaporated under reduced pressure, the residue was extracted with 100 mL of ethyl ether and washed with100 mL of water. The organic layer was dried over MgSO4 anhydrous. Ethyl ether was then evaporated and the resulted viscous liquid was purified by flash column chromatography (SiO2; 4:1 then 3:1 and finally 1:1hexanes/ethyl acetate).

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:
Article; Luu, Quang H.; Guerra, Jorge D.; Castaneda, Cecilio M.; Martinez, Manuel A.; Saunders, Jong; Garcia, Benjamin A.; Gonzales, Brenda V.; Aidunuthula, Anushritha R.; Mito, Shizue; Tetrahedron Letters; vol. 57; 21; (2016); p. 2253 – 2256;,
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Synthetic Route of 62257-15-2,Some common heterocyclic compound, 62257-15-2, name is 2-Fluoro-5-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.

E. Preparation of N-benzyl-2-fluoro-5-methoxyaniline This procedure was patterned after that of Tietze and Grote, Chem Ber. 126(12), 2733 (1993). A solution of 2.73 g of 2-fluoro-5-methoxyaniline and 2.67 g of benzaldehyde in 48 ml of methanol was treated with 3.43 g of zinc chloride and then cooled in an ice bath. Sodium cyanoborohydride (1.58 g) was added in small poroom temperature ions over 30 minutes and the reaction was stirred for five hours at room temperature. After evaporation of the solvent, the residue was slurried in 40 ml of 1 N sodium hydroxide solution and then extracted twice with ether. The extracts were washed with water and then with brine, dried over magnesium sulfate and concentrated. The residue was recrystallized from hexane to afford 2.61 g and the mother liquors were chromatographed on silica gel using 20:1 hexane/ether to afford another 1.4 g of the subtitle compound (90%). mp. 56-58C

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Fluoro-5-methoxyaniline, its application will become more common.

Reference:
Patent; ELI LILLY AND COMPANY; EP950657; (1999); A2;,
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Some common heterocyclic compound, 104197-14-0, name is 4-Bromo-2,6-difluoroanisole, molecular formula is C7H5BrF2O, 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: 4-Bromo-2,6-difluoroanisole

The mixture of 5-bromo-l,3-difluoro-2-methoxy-benzene (2.6 g, 11.7 mmol), ethynyl (trimethyl)silane (1.145g, 11.7 mmol), N,N-Diisopropylethylamine (1.205 g, 9.33 mmol), Copper(I)Iodide (177.6 mg, 0.93 mmol) and Bis(Triphenylphosphine)palladium (II) chloride (340.4 mg, 0.47 mmol) in THF (20 mL) were heated at 60 C under a nitrogen atmosphere for 16 hours. Added water (50 mL) and extracted by EtOAc (60 mL), washed EtOAc phase with water (50 mL), brine (50 mL), dried over Na2S04, filtered and concentrated to give a residue. The residue was purified by slica gel column (pure PE) to afford the title compound as an oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 104197-14-0, its application will become more common.

Reference:
Patent; GALECTO BIOTECH AB; BRIMERT, Thomas; JOHNSSON, Richard; LEFFLER, Hakon; NILSSON, Ulf; ZETTERBERG, Fredrik; (284 pag.)WO2016/120403; (2016); 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. 2398-37-0, name is 1-Bromo-3-methoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 2398-37-0

1-Bromo-3-methoxybenzene (20 mmol), CH2Cl2 (50 mL) and CH3COCl (1.5 eq., 30 mmol) were added to a 250 mL round-bottom flask. After cooled to -20 oC, AlCl3 (3 eq., 8.0 g) was added to the mixture slowly. The reaction was stirred vigorously for 3 h at -20 oC. Ice water ( 80 mL ) was added to the flask and the mixture was extracted with CH2Cl2 (30 mL x 3), dried by anhydrous Na2SO4. Evaporation of the solvent followed by purification on silica gel provided 1-(2-bromo-4-methoxyphenyl)ethanone, yield 75%.

The synthetic route of 2398-37-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lou, Zhen-Bang; Pang, Xin-Long; Chen, Chao; Wen, Li-Rong; Li, Ming; Chinese Chemical Letters; vol. 26; 10; (2015); p. 1231 – 1235;,
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Adding a certain compound to certain chemical reactions, such as: 6298-96-0, name is 1-(4-Methoxyphenyl)ethylamine, 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 6298-96-0, name: 1-(4-Methoxyphenyl)ethylamine

General procedure: To a solution of compound 93 (0.12 g, 0.41 mmol), sodium tert-butoxide (0.145 g, 1.51 mmol), phenylmethanamine (0.13 mL, 1.16 mmol) in toluene (5 mL) at room temperature were added palladium acetate (6 mg, 0.025 mmol) and tBu3P (0.017 mL, 0.07 mmol). The mixture was sealed in a microwave tube and heated to 85 C overnight. The reaction was monitored by TLC. Upon completion, the mixture was extracted with EtOAc (3 * 20 mL). The combined organic fractions were washed with brine, dried with Na2SO4, then concentrated by evaporation under reduced pressure. Purification by silica gel column chromatography (gradient elution, gradient 0-25% EtOAc/60-90 C petroleum ether) gave compound 32 as a yellow soild (0.077 g, 0.24 mmol, 59% yield).

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:
Article; Hu, Jianping; Wang, Yingqing; Li, Yanlian; Xu, Lin; Cao, Danyan; Song, ShanShan; Damaneh, Mohammadali Soleimani; Wang, Xin; Meng, Tao; Chen, Yue-Lei; Shen, Jingkang; Miao, Zehong; Xiong, Bing; European Journal of Medicinal Chemistry; vol. 137; (2017); p. 176 – 195;,
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Application of 1535-75-7, 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 1535-75-7 as follows.

(Formula 1-2: methyl 4-(((2-(trifluoromethoxy)phenyl)amino)methyl)benzoate)[1695][1696]Compound ofFormula 1-1(2-(trifluoromethoxy)aniline; 0.385 mL, 4.625 mmol), methyl 4-(bromomethyl)benzoate (1.271 g, 5.550 mmol) and DIPEA (1.228 mL, 6.937 mmol) were dissolved in acetonitrile (5 mL) at room temperature and stirred at the same temperature for 16 hours. Water was poured into the reaction mixture, and the organic layer was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride aqueous solution, dehydrated with anhydrous magnesium sulfate, filtered, and then concentrated under reduced pressure. The concentrate was purified and concentrated by column chromatography (silica; ethyl acetate/hexane=20%) to give the desired compound ofFormula 1-2(0.806 g, 53.6%) in the form of a colorless liquid.

According to the analysis of related databases, 1535-75-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHONG KUN DANG PHARMACEUTICAL CORP.; LEE, Changsik; YANG, Hyun-Mo; CHOI, Hojin; KIM, Dohoon; KIM, Soyoung; HA, Nina; LIM, Hyojin; KO, Eunhee; YOON, Seongae; BAE, Daekwon; WO2014/178606; (2014); 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. 171290-52-1, name is 3,5-Dimethoxyphenylacetylene, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 171290-52-1

General procedure: 2-Iodo-N-phenyl-N-(trimethylsilylethynyl)benzenesulfonamide 18 (100 mg, 0.22 mmol), CuI (4.2 mg, 0.022 mmol), and PdCl2(PPh3)2 (7.7 mg, 0.011 mmol) were placed successively in a two-necked 100 mL flask containing a bar magnet and capped by a three-way stopcock. The reactor was purged of air (three vacuum-nitrogen cycles) before 5 mL of dry and degassed triethylamine and 3 mL of dry and degassed THF were added. 0.5 h later, the desired alkyne 19 (0.24 mmol) was added. The resulting mixture was stirred at room temperature and the reaction was followed by thin layer chromatography. When the reaction was complete, the solvents were removed under reduced pressure and the crude product was purified by column chromatography.

According to the analysis of related databases, 171290-52-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Etse, Koffi Senam; Dassonneville, Benjamin; Zaragoza, Guillermo; Demonceau, Albert; Tetrahedron Letters; vol. 58; 8; (2017); p. 789 – 793;,
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Reference of 5111-65-9, The chemical industry reduces the impact on the environment during synthesis 5111-65-9, name is 2-Bromo-6-methoxynaphthalene, I believe this compound will play a more active role in future production and life.

A solution of 6-methoxy-2-bromonaphthalene (25 g) in tetrahydrofuran (300 ml) was cooled at -78C under a nitrogen atmosphere. n-Butyllithium (2.66 M solution in hexane) (42 ml) was added dropwise thereto over 1.5 hours, and the solution was stirred for 30 minutes. Triisopropyl borate (26.5 ml) was added dropwise thereto for 30 minutes, then the solution was stirred for 40 minutes while warming from -78C to 0C. 1N hydrochloric acid (200 ml) and ethyl acetate (200 ml) were sequentially added thereto, the solution was stirred, extracted with ethyl acetate, then washed with brine, dried over anhydrous magnesium sulfate, then the solvent was evaporated in vacuo, the resulting solid was washed with a hexane-diethyl ether system to provide the title compound (18 g).1H-NMR (400MHz, DMSO-d6); delta (ppm): 3.86 (s, 3H), 7.12 (d, 1H), 7.26 (s, 1H), 7.72 (d, 1H), 7.76-7.84 (m, 2H), 8.07 (brs, 2H), 8.27 (s, 1H).

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, 2-Bromo-6-methoxynaphthalene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Eisai Co., Ltd.; EP1577288; (2005); A1;,
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Reference of 20469-65-2, 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. 20469-65-2, name is 1-Bromo-3,5-dimethoxybenzene, This compound has unique chemical properties. The synthetic route is as follows.

Under a nitrogen atmosphere,2.92 g, 13.82 mmol of 1-bromo-3,5-dimethoxybenzene was dissolved in 80 ml of dry DMF,Continuous addition of 3.86g,15.20 mmol of pinacol diboron,2.10 g, 20.73 mmol KOAc,1.56 g, 1.91 mmol PdCl2 (dppf) · CH2Cl2,The mixture was stirred at 80 C for 39 hours,The resulting solution was distilled under reduced pressure to remove DMF,CH2Cl2 extraction of organic phase,Na2SO4 dehydration,After distillation under reduced pressure by column chromatography.The stationary phase was a spherical silica gel of 63 to 210 m,The EtOAc / CH3 (CH2) 4CH3 solution with a fixed phase diameter of 7.5 cm in height of 8 cm and a mobile phase of 40/60,The purified white material was purified by column chromatography with 2.18 g of 5.22 mmol of 4-bromo-2,6-bis [2- (1-methyl) benzimidazolyl] pyridine in 60 ml of anhydrous DMF,2.79 g, 28.46 mmol KOAc,0.87 g, 1.06 mmol PdCl2 (dppf) · CH2Cl2,The mixture was stirred at 80 C for 60 hours,The resulting solution was distilled under reduced pressure to remove DMF,CH2Cl2 extraction of organic phase,Dehydration of Na2SO4, distillation under reduced pressure by column chromatography,The stationary phase was a spherical silica gel of 63 to 210 m,Fixed phase diameter of 7.5cm height of 8cm,The mobile phase consisted of 60/40 EtOAc / CH3 (CH2) 4CH3 solution,The white intermediate 1 purified by column chromatography was dissolved in 50 ml of anhydrous CH2Cl2,In the ice bath slowly drip 1.0M, 15ml, 15mmol of BBr3 (dropping time 30min)After completion of the dropwise addition, the temperature was gradually raised to room temperature for 12 hours,The resulting solution was quenched by the dropwise addition of 20 ml of water in an ice-water bath,The aqueous phase was adjusted to pH to neutral and the organic phase was extracted with EtOAc.After washing with water, Na2SO4 was dehydrated, distilled under reduced pressure and washed with Hex. After filtration, the white intermediate 2 was recrystallized from DMSO / H2O and dissolved with 1.50 g of 4.45 mmol of 1- (4-bromobutyl) -pyrene 60 ml of DMF solution,1.52 g, 11.05 mmol of K2CO3 was added and stirred at 80 C for 90 h. The organic phase was extracted by distillation under reduced pressure. The organic phase was extracted with CH2Cl2 and dehydrated with Na2SO4. After distillation under reduced pressure, the column was purified by column chromatography using a spherical silica gel of 63 to 210 m A mixed solution of 30/70 EtOAc / CH2Cl2 with a diameter of 7.5 cm and a mobile phase of 30 cm and a mobile phase was purified by column chromatography to give the product Py2G1MeBip as a white product.

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-3,5-dimethoxybenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; KUNMING UNIVERSITY OF SCIENCE AND TECHNOLOGY; WANG, HUA; YANG, LI; LI, KONGZHAI; WEI, YONGGANG; ZHU, XING; (27 pag.)CN104231007; (2017); B;,
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Some common heterocyclic compound, 7252-83-7, name is 2-Bromo-1,1-dimethoxyethane, molecular formula is C4H9BrO2, 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. Application In Synthesis of 2-Bromo-1,1-dimethoxyethane

To a mixture of 4-hydroxybenzothioamide (30.64 g, 0.20 mol) and 2-bromo-l,l-dimethoxyethane (31.00 g, 0.20 mol) in EtOH (600 mL) was added 4-methylbenzenesulfonic acid (34.44 g, 0.20 mol) with stirring at rt. The reaction mixture was heated at 90 C for 24 h, then cooled to rt and concentrated in vacuo. The mixture was diluted with H20 (200 mL), adjusted to pH 10 with saturated NaHC03aqueous solution and extracted with DCM (200 mL x 3). The combined organic phases were concentrated in vacuo to give the title compound as s yellow solid (21.3 g, 60%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7252-83-7, its application will become more common.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; ZHANG, Jiancun; WANG, Xiaojun; LIN, Runfeng; CAO, Shengtian; WANG, Zhaohe; LI, Jing; WO2014/12360; (2014); A1;,
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