Author: Jessica.F

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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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. 2050-46-6, name is 1,2-Diethoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 1,2-Diethoxybenzene

G. 2-(3,4-Diethoxybenzoyl)[cis]cyclohexanecarboxylic Acid Prepared from 1,2-diethoxybenzene and cis-hexahydrophthalic anhydride as described for compound A. M.p.: low melting solid. 1 H-NMR(CDCl3): 1.28-2.27(m, 14H, 833 cyclohexane H, 2*C–CH3); 2.66(quintet, J=4.8 Hz, 1H, cyclohexane H); 3.91-3.97(m, 1H, C–CH(C)–C); 4.01-4.25(m, 4H, 2*O–CH2); 6.89(d, J=8.2 Hz, 1H, arom. H); 7.48-7.53 (m, 2H, arom. H)

According to the analysis of related databases, 2050-46-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Byk Gulden Lomberg Chemische Fabrik GmbH; US6103718; (2000); A;,
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Some common heterocyclic compound, 13321-74-9, name is 4-Bromo-2,5-dimethoxytoluene, molecular formula is C9H11BrO2, 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-2,5-dimethoxytoluene

General procedure: NaOt-Bu (0.240 g, 2.5 mmol), Pd(OAc)2 (0.006 g, 0.025 mmol) and [HPt-Bu3][BF4] (0.010 g, 0.035 mmol) were suspended in toluene (3 ml) in a 5 ml microwave vial. The appropriate 2-chloroaniline (0.50 mmol) and aryl bromide (0.50 mmol) were then added and the vial sealed. The reaction was then heated in the microwave reactor at 160 C for 3 h, allowed to cool, and then quenched by addition of aqueous HCl (2 M, 3 ml). The organic phase was extracted with CH2Cl2 (2×20 ml), dried (MgSO4), then filtered and the solvent removed under reduced pressure. The crude product mixture was then subjected to column chromatography (SiO2).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 13321-74-9, its application will become more common.

Reference:
Article; Bedford, Robin B.; Bowen, John G.; Weeks, Amanda L.; Tetrahedron; vol. 69; 22; (2013); p. 4389 – 4394;,
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4393-09-3, name is (2,3-Dimethoxyphenyl)methanamine, 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. category: ethers-buliding-blocks

To a solution of 2, 3-dimethoxybenzylamine (2.2 mL, 15.0 mmol) in 2-butanone (20 mL) was added 1,3-propane sultone (1.97 g, 15.8 mmol). The mixture was stirred at reflux for 2 hours. The reaction mixture was cooled to room temperature. The solid was collected by filtration, washed with acetone (2 x 25 mL) and dried in vacuo. The crude product was suspended in 90% Acetone/MeOH (75 mL). The suspension was stirred at reflux for 30 seconds, the solid was collected by filtration, and dried in vacuo ; affording compound AZ, 1.95 g (45%).

The synthetic route of 4393-09-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NEUROCHEM (INTERNATIONAL) LIMITED; WO2004/113275; (2004); A2;,
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Related Products of 59557-91-4, The chemical industry reduces the impact on the environment during synthesis 59557-91-4, name is 4-Bromo-2-methoxyaniline, I believe this compound will play a more active role in future production and life.

A stirred solution of NaNO2 (5.63 g, 81.7 mmol) in conc. HCl (6.2 ml) was cooled to 10 C. 4-bromo-2-methoxy-phenylamine (15 g, 74 mmol) in HOAc (100 ml) was added at such a rate that the temperature of the r.m. was maintained below 10 C. After addition was completed, the mixture was stirred at r.t. for 30 min. This solution was added dropwise, to a stirring solution of KI (37 g, 223 mmol) in 48% HBr (200 ml) at r.t. This mixture was stirred for 1 h and was then diluted with ice water (1000 ml). The resulting white precipitate was collected by filtration and washed with H2O, yielding a solid (a) and the mother liquor (b).The solid (a) was suspended in a mixture of DCM and a sat. aq. Na2CO3 solution. The resulting slurry was filtered over diatomaceous earth. The organic layer of the filtrate was washed with a diluted NH4OH solution until the disappearance of blue colour. The organic phase was dried (MgSO4), filtered and evaporated to yield a brown solid. The mother liquor (b) was basified by the addition of solid Na2CO3 and was then extracted with DCM. The combined organic extracts were washed with a diluted NH4OH solution until the disappearance of blue colour. The organic phase was dried (MgSO4), filtered and evaporated to give a brown solid.The 2 brown solids were combined, yielding 24.0 g of intermediate 54 (91%).

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

Reference:
Patent; Van Brandt, Sven Franciscus Anna; De Cleyn, Michel Anna Jozef; Gijsen, Henricus Jacobus Maria; Berthelot, Didier Jean-Claude; Surkyn, Michel; US2012/295891; (2012); A1;,
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