Tag: M.W=200-300

Application of 5467-58-3, 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 5467-58-3 as follows.

To a solution of 1-bromo-4-methoxynaphthalene (4.72 g, 20 mmoL) in 1, 4-dioxane /H2O (80 mL/20mL) was added 4, 4, 5, 5-tetramethyl-2- (1, 4-dioxaspiro [4.5] dec-7-en-8-yl) -1, 3, 2-dioxaborolane (5.32 g, 10 mmol), Pd (dppf) Cl2 (1462 mg, 2.0 mmol) and Cs2CO3 (9.75 g, 30 mmol) and the mixture was heated at 70 for 5 hours. Then evaporated the solvent under reduced pressure and the residue was purified by column chromatography (PE: EA=5: 1) to give product as an oil (4.1 g in 69% yield). [M+H] +=297.

According to the analysis of related databases, 5467-58-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BEIGENE, LTD.; WANG, Hexiang; GUO, Yunhang; REN, Bo; WANG, Zhiwei; ZHANG, Guoliang; ZHOU, Changyou; (353 pag.)WO2018/54365; (2018); 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. 701-07-5, name is 2-(2′-Bromophenoxy)propane, A new synthetic method of this compound is introduced below., Product Details of 701-07-5

An Et2O solution (10 mL) of I2 (1.21 g, 4.78 mmol) was added to a solid of 1 (0.72 g,0.79 mmol) to prepare the solution of diiodophenylarsine (2). Without isolation, thesolution of 2 was employed the subsequent reaction. To an Et2O solution (10 mL) of1-bromo-2-isopropoxybenzene (1.6 mL, 9.97 mmol) was added a hexane solution ofn-butyllithium (1.6 M, 6.0 mL, 9.6 mmol) at 0 C under N2 atmosphere, and the reactionmixture was stirred at the ambient temperature for 1 h. To the reaction mixture was thesolution of 2 was added at 0 C. The reaction temperature was raised to the ambienttemperature, and the reaction mixture was stirred for 5 h. The reaction was quenchedby distilled water (20 mL), and the products were extracted with EtOAc. The combinedorganic layers were dried over MgSO4, and volatiles were removed in vacuo. The residuewas subjected to recrystallization from EtOH, and washed with MeOH to obtaincolorless solids of 3c (1.52 g, 3.61 mmol, 72%). 1H NMR (CDCl3, 400 MHz) delta 7.34-7.24 (m,7H), 6.86 (t, J = 8.4 Hz, 2H), 6.83-6.77 (m, 4H), 4.50 (sep, J = 6.0 Hz, 2H), 1.18 (d, J = 6.0Hz, 6H), 1.08 (d, J = 6.4 Hz, 6H) ppm; 13C NMR (CDCl3, 100 MHz) delta 159.6, 139.9, 134.4,129.5, 129.4, 128.2, 127.9, 120.7, 112.1, 70.2, 21.9, 21.7 ppm. HR FAB-MS (m/z):calculated for C24H27O2As [M]+; 422.1227, observed; 422.1211.

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; Imoto, Hiroaki; Yamazawa, Chieko; Tanaka, Susumu; Kato, Takuji; Naka, Kensuke; Chemistry Letters; vol. 46; 6; (2017); p. 821 – 823;,
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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.

To anhydrous copper [(II)] chloride (6.3g, 47mmol) in acetonitrile (lOOmL) was added tert-butyl nitrite (6.85mL, [58MMOL),] followed dropwise by a solution of [2-BROMO-4- (TRIFLUOROMETHOXY)] aniline (lOg, 39mmol) in acetonitrile [(15ML).] The solution was stirred at ambient temperature for 1 hour then poured into hydrochloric acid (250mL, 2M). The suspension formed was extracted with diethyl ether [(2X250ML)] and the extracts were dried [(MGS04).] Concentration yielded the title compound as an oil (7.82g, [28MMOL).] [ON] (360 MHz, [CDCL3)] : 7.51 [(1H,] d, J 3.2Hz), 7.48 [(1H,] d, J 8.8Hz), 7.15 [(1H,] dd, J 3.2 and 8.8Hz).

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; MERCK SHARP & DOHME LIMITED; WO2004/31190; (2004); A1;,
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Some common heterocyclic compound, 17061-62-0, name is Bis(4-methoxybenzyl)amine, molecular formula is C16H19NO2, 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. COA of Formula: C16H19NO2

To a cooled (-35 C) solution of 4-Fluoro-3-nitrobenzenesulfonyl chloride (4.89 g, 20.42 mmol) in THF (50 mL) was added Triethylamine (3.13 mL, 22.46 mmol), followed by addition of Bis-(4-methoxybenzyl)amine (4.97 mL, 20.7 mmol) in THF (50 mL) solution over 30 min. while the temperature was kept at -35 C. After completion of the addition, the temperature was allowed slowly to warm to 0 C over 1 h., and the mixture was stirred at 0 C for an additional hour. The mixture was neutralized with 1 N HC1 to pH about 4-5 and diluted with EtOAc (100 mL). The organic layer was separated, washed with 1 N HC1 (10 mL), 7.5% NaHC03 aqueous solution (20 mL), and brine, dried over Na2S04, filtered, and concentrated under reduced pressure. The residue was treated with DCM (30 mL), and hexane was added to the suspension until it became cloudy. The resulting suspension was sonicated for 2 min. and left at r.t. for 1 h. The mixture was filtered and washed with hexane to afford the desired title product (6.85 g) without further purification. The mother liquid was concentrated under reduced pressure. The residue was treated with DCM (5 mL) and hexane was added as the procedures mentioned above to afford the additional 0.51 g of the title product. Total product 4-fluoro-N,N-bis[(4-methoxyphenyl)methyl]-3-nitro-benzenesulfonamide obtained is 7.36 g (78%). NMR (400 MHz, DMSO-de): d 8.18-8.23 (m, 2 H), 7.75-7.79 (q, 1 H), 7.08 (d, 4 H), 6.81 (d, 4 H), 4.31 (s, 4 H), 3.71 (s, 6 H). 19F NMR (376 MHz, DMSO-d6): d -112.54 (s, 1 F). LCMS calculated for C22H22FN2O6S (M+H)+: m/z = 461.11; found: 461.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 17061-62-0, its application will become more common.

Reference:
Patent; PRELUDE THERAPEUTICS, INCORPORATED; ZHUO, Jincong; LEAL, Raul; SHETTY, Rupa; LUENGO, Juan; COMBS, Andrew, Paul; (525 pag.)WO2020/97577; (2020); A1;,
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Reference of 886762-08-9, The chemical industry reduces the impact on the environment during synthesis 886762-08-9, name is 5-Bromo-2-(trifluoromethoxy)aniline, I believe this compound will play a more active role in future production and life.

General Procedure: Methyl 2-{[4-(chlorosulfonyl)-2,3-dimethylphenyl]oxy}propanoate (7) (4 g, 13.0 mmol) was dissolved in pyridine (10 mL). After 5 min, 3-bromo-2-chloroaniline (3.22 g, 15.6 mmol) was added. The reaction was complete within a few hours. The reaction mixture was then extracted using diethyl ether. The combined organic phases were washed with 1N HCl and brine, dried over sodium sulfate, filtered, and concentrated in vacuo to afford the title compound which was used without further purification.

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, 5-Bromo-2-(trifluoromethoxy)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Evans, Karen A.; Shearer, Barry G.; Wisnoski, David D.; Shi, Dongchuan; Sparks, Steven M.; Sternbach, Daniel D.; Winegar, Deborah A.; Billin, Andrew N.; Britt, Christy; Way, James M.; Epperly, Andrea H.; Leesnitzer, Lisa M.; Merrihew, Raymond V.; Xu, Robert X.; Lambert, Millard H.; Jin, Jian; Bioorganic and Medicinal Chemistry Letters; vol. 21; 8; (2011); p. 2345 – 2350;,
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These common heterocyclic compound, 1663-61-2, name is (Triethoxymethyl)benzene, 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. Formula: C13H20O3

To a solution of compound 13 (57.1 mg, 0.245 mmol) in 2 mL CH3CN, triethylorthobenzotate (170 muL, 0.735 mmol) and camphorsulfonic acid (11.4 mg,0.049 mmol) were added. The mixture was refluxed at 85 C for 4 h afterwhich TLC indicated full conversion and quenched by adding Et3N. The mixture was concentrated and theresidue was re-dissolved in 1 mL pyridine and 0.5 mL Ac2O was added. The mixture was stirred at roomtemperature for 2 h after which TLC indicated full conversion. The mixture was concentrated underreduced pressure. The residue was dissolved in 2 mL CH3OH and 1 M HCl (1.5 mL) was added. Themixture was stirred for 5 min and extracted with CH2Cl2. The combined organic layers were dried overNa2SO4 and concentrated. The residue was purified by column chromatography to afford 14 as light yellowsyrup (79.1 mg, 85percent).

The synthetic route of (Triethoxymethyl)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Lihao; Fan, Fei; Wu, Haotian; Gao, Lei; Zhang, Ping; Sun, Tiantian; Yang, Chendong; Yu, Guangli; Cai, Chao; Synlett; vol. 29; 20; (2018); p. 2701 – 2706;,
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Electric Literature of 74137-36-3, A common heterocyclic compound, 74137-36-3, name is 1,3-Dibromo-5-methoxybenzene, molecular formula is C7H6Br2O, 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 1.6 M solution of n-butyllithium in hexane (5.65 mL, 9.04 mmol) was dissolved in dry toluene (50 mL) under dry argon and cooled to -5¡ã C. Then a 2M solution of n-butylmagnesium chloride (2.26 mL, 4.52 mmol) was added slowly with the temperature held below 0¡ã C. over a period of 15 min. Stirring was continued for 45 min at -5¡ã C., followed by drop wise addition of a solution of 1,3-dibromo-5-methoxy-benzene (3.00 g, 11.3 mmol) in toluene (30 mL) with the temperature held below 0¡ã C. The mixture was stirred for 45 min at -5¡ã C. A solution of iodine chloride (1.83 g, 11.3 mmol) in methylene chloride (20 mL) was added in the described manner and stirring continued for additional 20 min at -5¡ã C. The mixture was warmed to room temperature. Water (50 mL) and toluene (50 mL) were added and the layers were separated. The organic layer was washed with a saturated aqueous solution of Na2S2O3 (2.x.30 mL), water and brine (30 mL). The organic layer was dried (MgSO4) and concentrated to give the crude product which was purified by flash chromatography on silica gel (100 g, AcOEt/heptane 1:9). 1-Bromo-3-iodo-5-methoxy-benzene (2.12 g, 60percent) was obtained as a yellow oil, which crystallized quickly upon standing.

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; Kelly, Martha; Lee, Younghee; Liu, Bin; Fujimoto, Ted; Freundlich, Joel; Dorsey, Bruce D.; Flynn, Gary A.; Husain, Arifa; US2006/270686; (2006); 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. 589-10-6, name is (2-Bromoethoxy)benzene, A new synthetic method of this compound is introduced below., Computed Properties of C8H9BrO

To a stirred solution of (2-bromoethoxy)benzene (1 g, 5 mmol) in CH3CN (50 mL) wereadded methyl piperidine-4-carboxylate (0.715g, 5 mmol, 1 equiv) and sodium bicarbonate (1.26 g, 15 mmol, 3 equiv) at room temperature. The reaction mixture was heated atlOOand stirred for 16 h. After completion, the reaction mixture was diluted with water and extracted with EtOAc. The combined organic extract was washed with brine, filtered and dried over sodium sulphate. The solvent was removed under reduced pressure. Purificationusing silica gel column chromatography (20% EtOAc Hexanes as eluent) afforded 1 gmethyl 1-(2-phenoxyethyl) piperidine-4-carboxylate (Yield = 76%). ESI+ MS: m/z: 264.1 ([M+Hj).

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; THE BROAD INSTITUTE, INC.; MASSACHUSETTS INSTITUTE OF TECHNOLOGY; HOLSON, Edward; WAGNER, Florence, Fevrier; WEIWER, Michel; SCOLNICK, Edward; PALMER, Michelle; LEWIS, Michael; PAN, Jennifer, Q.; ZHANG, Yan-Ling; XU, Qihong; (323 pag.)WO2016/100823; (2016); A1;,
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Synthetic Route of 886762-08-9, The chemical industry reduces the impact on the environment during synthesis 886762-08-9, name is 5-Bromo-2-(trifluoromethoxy)aniline, I believe this compound will play a more active role in future production and life.

General procedure: 1,1-Cyclopropanedicarboxylic acid (5) (12.0 g, 15.4 mmol) was dissolved in anhydrous THF (50 mL). Then triethanolamine (2.0 mL,13.9 mmol) was added to the mixture and the mixture was stirred on the ice-bath for 30 min. SOCl2 (1.2 mL, 16.66 mmol) was then added. Stirring was continued for 2h, a solution of 3,5-dimethylaniline 6 (3.6 g, 15.4 mmol) in anhydrous THF (10 mL) was added and continued stirring for 2h, after that, the ice bath was removed, and the mixture was stirred at room temperature overnight. After the completion of the reaction, the mixture was filtered and concentrated in vacuo. The residues was purified by silica gel flash chromatography (PE/AcOEt = 5:1) to yield 7 as white solid (0.8 g, 30.7%).

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, 5-Bromo-2-(trifluoromethoxy)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Li, Chuansheng; Shan, Yuanyuan; Sun, Ying; Si, Ru; Liang, Liyuan; Pan, Xiaoyan; Wang, Binghe; Zhang, Jie; European Journal of Medicinal Chemistry; vol. 141; (2017); p. 506 – 518;,
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Application of 1663-61-2, A common heterocyclic compound, 1663-61-2, name is (Triethoxymethyl)benzene, molecular formula is C13H20O3, 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 intermediate 2 (4 g, 15 mmol), acetic anhydride(5.8 g, 56.9 mmol), and triethyl orthobenzoate (10.1 g, 45 mmol)in toluene (25 mL) was stirred for 5 h at 110 C. After that time,the solvent was concentrated. The precipitate was filtered off,and dried to give 3 as a yellow solid (4.56 g, 76percent). 1H NMR(400 MHz, DMSO-d6) d 8.75 (d, J = 1.3 Hz, 1H), 8.11 (d, J = 8.1 Hz,1H), 7.93 (dd, J = 8.1, 1.6 Hz, 1H), 7.61?7.55 (m, 3H), 7.51 (dd,J = 7.7, 1.8 Hz, 2H), 4.86 (s, 2H), 4.03 (m, 2H), 3.89 (s, 3H), 1.36(t, J = 7.0 Hz, 3H). ESI-MS m/z: 400.0 [M+H]+.

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

Reference:
Article; Qin, Mingze; Yan, Shuang; Wang, Lei; Zhang, Haotian; Tian, Ye; Zhao, Yanfang; Gong, Ping; Bioorganic and Medicinal Chemistry; vol. 25; 6; (2017); p. 1778 – 1786;,
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