Ethers-buliding-blocks

Synthetic Route of 116557-46-1, A common heterocyclic compound, 116557-46-1, name is 3-Bromo-2-methoxyaniline, molecular formula is C7H8BrNO, 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.

Preparation 10 To a reaction vial charged with 3-bromo-2-methoxyaniline (from Step 4 of Preparation 9, 1.12 g, 5.54 mmol), l-methyl-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)-lH-pyrazole (1.499 g, 7.21 mmol) in dioxane (6 mL) was added aqueous potassium phosphate (2.0 M) (5.54 ml, 11.09 mmol). The resulting mixture was deoxygenated by bubbling argon through the mixture for ~5 min. PdCl2(dppf) (0.122 g, 0.166 mmol) was then added and the mixture was heated at 110 C for 2h. The reaction was cooled, diluted with EtOAc (200 mL), washed with water, brine, dried over anhyd sodium sulfate, filtered and concentrated to afford tan oil as the crude product mixture. This material was purified by silica gel flash chromatography using hexanes/ethyl acetate mixtures as the eluant. Fractions containing the desired product were collected, combined, and concentrated under vacuum to afford 0.87 g (77%) of the desired product (Preparation 10) as an oil which solidified upon standing. HPLC (method N) = 0.89 min. LCMS MH+ 204.1.

The synthetic route of 116557-46-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; MOSLIN, Ryan M.; WEINSTEIN, David S.; WROBLESKI, Stephen T.; ZHANG, Yanlei; TOKARSKI, John S.; MERTZMAN, Michael E.; LIU, Chunjian; WO2015/69310; (2015); 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. 112970-44-2, name is 2-Bromo-3-methoxyaniline, A new synthetic method of this compound is introduced below., category: ethers-buliding-blocks

A mixture of compound 58-1 (200 mg, 989.86 umol, 1 eq.), compound 58-1 (243.76 mg, 1.19 mmol, 1.2 eq.) and EDCI (284.64 mg, 1.48 mmol, 1.5 eq.) in pyridine (3 mL) was stirred at 20 C for 12 hours. The mixture was diluted with EtOAc (30 mL), washed with 1 N hydrochloric acid solution (20 mL*3) dried with sodium sulfate, filtered and concentrated. The residue was purified by prepTLC (PE:EA = 3:1) to give compound 58-2 (150 mg,, yield: 38 %) as brown oil. LCMS: 391.1 [M+ 11

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; TREVENA, INC.; PITIS, Philip Michael; BOYD, Robert Eugene; DAUBERT, Tamara Ann Miskowski; HAWKINS, Michael John; LIU, Guodong; SPEERSCHNEIDER, Aimee Crombie; (355 pag.)WO2018/231745; (2018); 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. 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine, This compound has unique chemical properties. The synthetic route is as follows., category: ethers-buliding-blocks

Saturated NaHC03 (100 mL) was added to a solution of (2,4- dimethoxyphenyl)methanamine (10 mL, 66.4 mmol) in CH2CI2 (100 mL) and the mixture was stirred vigorously at 25 C for 15 min. Then thiophosgene (10 mL, 131 mmol) was added via syringe to the bottom layer. The mixture was stirred at 25 C for 1.5 h. The aqueous layer was separated and the organic layer was washed with brine (100 mL), dried over NaSC>4, filtered, and concentrated in vacuo to afford l-(isothiocyanatomethyl)-2,4-dimethoxy benzene. HNMR (400 MHz, CDCI3): delta 7.19 (d, J = 7.6 Hz, 1H), 6.47-6.50 (m, 2H), 4.61 (s, 2H), 3.84 (s, 3H), 3.82 (s, 3H).

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; MERCK SHARP & DOHME CORP.; THE WALTER AND ELIZA HALL INSTITUTE OF MEDICAL RESEARCH; KHAN, Tanweer, A.; CUMMING, Jared, N.; OLSEN, David, B.; BODDEY, Justin, A.; COWMAN, Alan, F.; SLEEBS, Brad, E.; (86 pag.)WO2017/142825; (2017); A2;,
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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 14869-41-1 as follows. Computed Properties of C4H7ClO3

2-(2-Chloroethoxy)acetic acid (1.0 g, 7.2 mmol) was dissolved in dichloromethane (10.0 mL)Then oxalyl chloride (1.2 mL, 14 mmol) was added and stirred at room temperature for 4 hours.Evaporate the solvent under reduced pressure.The crude product was used directly in the next reaction.

According to the analysis of related databases, 14869-41-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Wang Xiaojun; Zuo Yinglin; Yu Chuan; Yang Chuanwen; Wang Jiancheng; Li Jing; Cao Shengtian; Wu Fangyuan; Zhang Yingjun; S ¡¤geerdeman; (79 pag.)CN108690016; (2018); A;,
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Reference of 3616-56-6, 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. 3616-56-6, name is 2,2-Diethoxy-N,N-dimethylethanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Synthesis Example B17Synthesis of 8-bromo-12H-benzofuranyl[2,3-a]carbazole (compound 17)Under nitrogen, compound 16 (4.6 g, 1 eq) is initially charged and dissolved with acetic acid (185 ml) while heating to reflux.Then (dimethylamino)acetaldehyde diethyl acetal (95percent; 25 g, 10 eq.) is added dropwise to the reaction within 1 h and the mixture is stirred at reflux for 7 h.The mixture is cooled to room temperature and diluted with methylene chloride.In a separating funnel, the organic phase is washed with distilled water and then with saturated NaCl solution.The organic phase is dried with sodium sulfate and concentrated. LC (reverse phase, acetonitrile) gives 1.35 g of product (27.3percent yield).1H NMR (CD2Cl2; 400 MHz): delta=8.73 (s, 1H), 8.17 (s, 1H), 8.16 (d, 1H), 8.08 (d, 1H), 7.78 (d, 1H), 7.60 (d, 1H), 7.56 (m, 2H), 7.49 (dd, 1H), 7.31 (dd, 1H).

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

Reference:
Patent; BASF SE; OSRAM OPTO SEMICONDUCTORS GMBH; KONINKLIJKE PHILIPS ELECTRONICS N.V.; US2011/266528; (2011); A1;,
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Related Products of 35896-58-3, These common heterocyclic compound, 35896-58-3, name is 1,2,3,4-Tetramethoxy-5-methylbenzene, 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.

A mixture of 2,3,4,5-tetramethoxytoluene (2.12 g, 10 mmol) and 1,1-dichlorodimethyl ether (1.8 mL, 20 mmol) in DCM (200 mL) was stirred at room temperature (rt), then the solution was allowed to cool to 0 oC and was added titanium tetrachloride (2.18 mL, 20 mmol). The mixture was allowed to warm to rt and stirred for 4 hours. The ice water was added slowly to quench the reaction and extracted with DCM, washed with brine and dried over Na2SO4, filtered and evaporated in vacuo. The resulting residue was purified by flash column chromatography on silica gel (EtOAc / petroleum ether = 1 / 20) to yield the target products (2 g, 83%) as colorless oil. 1H NMR (400 MHz, CDCl3) delta 10.43 (s, 1H), 4.02 (s, 3H), 3.94 (s, 3H), 3.91 (s, 3H), 3.76 (s, 3H), 2.46 (s, 3H). MS (ESI): m/z 241.1 [M+H]+.

The synthetic route of 35896-58-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ding, Yuyang; Tang, Fei; Xue, Xiaoqian; Luo, Jinfeng; Hussain, Muzammal; Huang, Yanhui; Wang, Zhen; Jiang, Hao; Tu, Zhengchao; Zhang, Jiancun; Bioorganic Chemistry; vol. 89; (2019);,
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171290-52-1, name is 3,5-Dimethoxyphenylacetylene, 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. name: 3,5-Dimethoxyphenylacetylene

A mixture of (S)-3-(5-amino-3-bromo-4-cyano-1H-pyrazol-1-yl)pyrrolidine-1-carboxylic acid tert-butyl ester 7c (5 g, 14.1 mmol), cuprous iodide (0.6 g, 2.8 mmol), triethylamine (9 mL), [1,1′-bis(diphenylphosphino)ferrocene]palladium dichloride (2 g, 2.8 mmol) and N,N-dimethylformamide (150 mL) was heated to 80 C. under argon, and then 1-ethynyl-3,5-dimethoxybenzene (14 g, 84.5 mmol) was added in portions, next stirred for 2 hours, and then cooled to room temperature, poured the reaction solution into water, extracted with ethyl acetate (200 mL*3); next the organic phases were combined and dried over anhydrous sodium sulfate, the desiccant was removed by filtering, and the reaction system was concentrated under reduced pressure, the residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=5/1), so as to obtain the title product (S)-3-(5-amino-4-cyano-3-((3,5-dimethoxyphenyl)ethynyl)-1H-pyrazol-1-yl)pyrrolidine-1-carboxylic acid tert-butyl ester 7d (5 g, brown oil), and the yield was 81%. MS m/z (ESI): 382[M+1-56]

The synthetic route of 171290-52-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BEIJING INNOCARE PHARMA TECH CO., LTD.; Chen, Xiangyang; Gao, Yingxiang; Kong, Norman Xianglong; (59 pag.)US2019/210997; (2019); A1;,
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Adding a certain compound to certain chemical reactions, such as: 588-96-5, name is p-Bromophenetole, 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 588-96-5, SDS of cas: 588-96-5

Preparation Example 6 Synthesis of 1-(benzyloxy)-2-bromo-4-(4-ethoxybenzyl)benzene; Benzyl bromide (3.1 mL, 0.026 mol) was added to a mixture of 3-bromo-4-hydroxybenzaldehyde (5.0 g, 0.025 mol), tetrabutylammonium iodide (0.92 g, 2.5 mmol), potassium carbonate (6.9 g, 0.050 mol) and N,N-dimethylformamide (70 mL) at room temperature and stirred for 2.5 hours. An ice-water mixture (100 mL) was poured to the reaction mixture and the resultant solution was stirred for one hour. A resulting precipitate was filtered and dried to obtain 4-benzyloxy-3-bromobenzaldehyde (7.1 g, 98%) as a pale yellow powder. Then, 1.6 M n-butyllithium hexane solution (22.9 mL) was added to a mixture of 4-bromophenetole (7.3 g, 0.037 mol) and tetrahydrofuran (70 mL) at -78C. After stirred for 0.5 hours, 4-benzyloxy-3-bromobenzaldehyde (7.0 g, 0.024 mol) in a tetrahydrofuran (70 mL) solution was added and further stirred for 15 minutes, and the reaction mixture was warmed to room temperature. After the reaction mixture was added with a saturated ammonium chloride aqueous solution and extracted with ethyl acetate, the organic phase was washed with brine and dried with anhydrous magnesium sulfate. After the desiccant was filtered off, the residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to obtain colorless oily [4-(benzyloxy)-3-bromophenyl](4-ethoxyphenyl)methanol (8.7 g, 86%). Then, Et3SiH (6.7 mL, 0.042 mol) and BF3¡¤Et2O (2.7 mL, 0.021 mol) were added sequentially to a chloroform (90 mL) solution of [4-(benzyloxy)-3-bromophenyl](4-ethoxyphenyl)methanol (8.7 g, 0.021 mol) at -15C. After stirred for one hour, the reaction mixture was warmed to room temperature. After the reaction mixture was added with a saturated sodium carbonate aqueous solution and extracted with chloroform, the organic layer was washed with brine and dried with anhydrous magnesium sulfate. After the desiccant was filtered off, the residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to obtain a colorless oily title compound (8.8 g, quant). 1H NMR (300 MHz, CHLOROFORM-d) delta ppm 1.40 (t, J=7.0 Hz, 3 H) 3.82 (s, 2 H) 4.00 (q, J=7.0 Hz, 2 H) 5.12 (s, 2 H) 6.78 – 6.87 (m, 3 H) 6.98 – 7.10 (m, 3 H) 7.27 – 7.50 (m, 6 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, p-Bromophenetole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD; EP1845095; (2007); 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 59557-91-4 as follows. name: 4-Bromo-2-methoxyaniline

Step 1: To a solution of 4-bromo-2-methoxyaniline (2.0 g, 9.9 mmol) in MeCN (50 mL) was added para-toluenesulfonic acid (5.1 g, 27 mmol). The resulting mixture was cooled in an ice water bath. A solution of NaNO2 (1.36 g, 19.7 mmol) and KI (4.11 g, 24.8 mmol) in water (50 mL) was then added, and the resulting mixture was stirred for 5 min. The mixture was then removed from the ice water bath. Once consumption of starting material was observed, the reaction mixture was partitioned between water and EtOAc. The organic phase was concentrated and the resulting crude residue was purified by silica gel chromatography to afford 4-bromo-1-iodo-2-methoxybenzene

According to the analysis of related databases, 59557-91-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Gilead Scientific Systems, Inc.; Cory, Kevin S; Doo, Jimin; Farrand, Julie; Guerrero, Juan A; Katana, Ashley A; Cato, Daryl; Laisaweed, Scott I; Lee, Jiayao; Lingco, John O; Nicolaus, May; Notte, Gregory; Phyen, Hyeoung-Jung; Sangy, Michael; Sumit, Arun C; Adam J, Surayyah; Stephens, Cork L; Venkatraman, Chandrasekar; Watkins, William J; Yang, Jong Yu; Jabloki, Jeff; Jifel, Shiela; Ro, Jennifer; Lee, Sung H; Jao, Chung Dong; Grove, Jeffery; Su, Jianjun; Blomgren, Peter; Mitchell, Scott A; Shyung, Jin Ming; Chandrasekar, Jayaraman; (460 pag.)KR2016/37198; (2016); A;,
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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. 109-85-3, name is 2-Methoxyethylamine, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2-Methoxyethylamine

[00580] To a solution of Example 116a (528 mg, 3.0 mmol) and Example 116b (450 mg, 6.0 mmol) in DMSO (4 mL) was added NN-diisopropylethylamine (780 mg, 6.0 mmol). The mixture was heated at 135C for 4 h. The reaction mixture was cooled to r.t., diluted with H20 (20 mL), and then extracted with EtOAc (100 mL). The organic layer was dried over Na2S04, filtered and concentrated under reduced pressure to give the desired product Example 116c (620 mg, yield 90%) as a white solid. LCMS [M+l] + = 230.9/232.9.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 109-85-3.

Reference:
Patent; FRONTHERA U.S. PHARMACEUTICALS LLC; JIN, Bohan; DONG, Qing; HUNG, Gene; (214 pag.)WO2019/51265; (2019); A1;,
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