Month: March 2021

Synthetic Route of 207226-31-1, These common heterocyclic compound, 207226-31-1, name is 1,3-Dibromo-5-(trifluoromethoxy)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.

EXAMPLE 57 6-(3-Bromo-5-trifluoromethoxy-Phenyl)-4,4-dimethyl-1,4-dihydrobenzo[d][1,3]-oxazin-2-one Prepared from (4,4-dimethyl-1,4-dihydro-2-oxo-2H-3,1-benzoxazin-6-yl)boronic acid and 1,3-dibromo-5-trifluoromethoxybenzene according to Procedure B. White solid: mp 214-216 C.; 1H-NMR (DMSO-d6) delta10.4 (s, 1H), 7.99 (s, 1H), 7.73 (s, 1H), 7.68-7.62 (m, 3H), 6.97 (d, 1H, J=8.0 Hz), 1.68 (s, 6H); MS (ESI) m/z 414 ([M’H]-, 100%); Anal. Calc. For C17H13BrF3NO3: C, 49.06, H, 3.15, N, 3.37. Found: C, 49.16, H, 3.05, N, 3.30.

The synthetic route of 207226-31-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wyeth; Ligand Pharmaceuticals, Inc.; US6444668; (2002); B1;,
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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. 886762-08-9, name is 5-Bromo-2-(trifluoromethoxy)aniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 5-Bromo-2-(trifluoromethoxy)aniline

240 g (0.937 mol) of 5-bromo-2-(trifluoromethoxy)aniline were dissolved in 2400 mL of anh toluene. 112 mL (1.406 mol) of chloroacetyl chloride were added. It was stirred for 2 h at 100 C. The reaction mixture was concentrated on the rotavap. The residue was treated with 600 mL of cyclopentyl methyl ether and concentrated again. This procedure was performed twice yielding 324 g of the title compound. 1H-NM (400MHz, DMSO-d6): delta [ppm]= 4.39 (s, 2H), 7.40 – 7.44 (m, 1H), 7.49 (dd, 1H), 8.20 (d, 1H), 10.23 (s, 1H). LC-MS (Method 4): Rt = 1.27 min; MS (ESIpos): m/z = 332 [M+H]+.

The synthetic route of 886762-08-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; THEDE, Kai; BENDER, Eckhard; SCOTT, William J.; RICHTER, Anja; ZORN, Ludwig; LIU, Ningshu; MOeNNING, Ursula; SIEGEL, Franziska; GOLZ, Stefan; HAeGEBARTH, Andrea; LIENAU, Philip; PUEHLER, Florian; BASTING, Daniel; SCHNEIDER, Dirk; MOeWES, Manfred; GEISLER, Jens; WO2015/140196; (2015); 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. 1462-37-9, name is ((2-Bromoethoxy)methyl)benzene, This compound has unique chemical properties. The synthetic route is as follows., Formula: C9H11BrO

General procedure: To a stirred solution of 1-(2-pyridyl)-b-carboline (0.245 g,1 mmol) in 10 mL DMF, sodium hydride (50% in mineral oil, 0.048 g,1 mmol) and bromo-hydrocarbon (1 mmol) was added. The reactionmixturewas stirred at room temperature for 1 h. After reactionwas finished, the mixture was poured into ice water and extractedwith ethyl acetate. The organic layer was washed with water anddried. Removal of the solvent gave the crude product that waspurified by silica gel column (dichloromethane: methanol 100:1 as the eluent). The solvent was removed and the product wasobtained.

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 1462-37-9.

Reference:
Article; Lu, Xing; Liu, Yan-Cheng; Orvig; Liang, Hong; Chen, Zhen-Feng; European Journal of Medicinal Chemistry; vol. 181; (2019);,
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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. 5905-69-1, name is 1-Bromo-4-(difluoromethoxy)benzene, A new synthetic method of this compound is introduced below., Product Details of 5905-69-1

Step 4) 1-difluoromethoxy-4-{3-[3-(2-fluoro-ethyl)-cyclobutyl]phenyl-ethynyl}benzene {3-[3-(2-Fluoro-ethyl)-cyclobutyl]-phenylethynyl}-triisopropyl-silane (349 mg, 0.973 mmol) was dissolved in THF (2 ml) and treated with a 1M solution of tetrabutylammonium fluoride (TBAF) in THF (2 ml) at room temperature. The crude product obtained from aqueous work-up was placed in a CEM snap top microwave vial and combined with 1-Bromo-4-Difluoromethoxybenzene (300 mg 1.30 mmol), copper iodide (35 mg, 0.131 mmol), tetrakis(triphenylphosphine)palladium (70 mg, 0.060 mmol) and triethylamine (4.3 g, 42.5 mmol). The vial was quickly agitated then irradiated in a CEM Explorer microwave instrument for 30 minutes at 80 C. Purification by column chromatography (gradient; 0%, then 5% EtOAc in hexanes) afforded an oil 178 mg (53%). 1H NMR (400 MHz, DMSO-d6) delta ppm 1.68-1.80 (m, 2H) 1.85-2.11 (m, 2H) 2.17-2.36 (m, 2H) 2.38-2.43 (m, 1H) 3.28-3.65 (m, 1H) 4.24-4.52 (m, 2H) 7.01-7.47 (m, 5H) 7.18 (d, J=8.8 Hz, 2H) 7.58 (d, J=8.8 Hz, 2H).

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; WYETH; US2009/48320; (2009); A1;,
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Synthetic Route of 22094-18-4, These common heterocyclic compound, 22094-18-4, name is 1,3-Dibromo-2,2-dimethoxypropane, 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.

Intermediate 314A: 1-(4-Bromophenyl)-3,3-dimethoxycyclobutanecarbonitrile To a suspension of NaH (0.733 g, 18.32 mmol, 60% in mineral oil) in DMF (14 mL) was added 2-(4-bromophenyl)acetonitrile (1.796 g, 9.16 mmol) followed by 1,3-dibromo-2,2-dimethoxypropane (2.0 g, 7.64 mmol) and the reaction mixture was heated to 60 C. and stirred for 12 h. The reaction mixture was cooled to RT, poured into water (150 mL) and extracted with EtOAc (3*40 mL). The combined organic layer was washed with brine, dried over Na2SO4, filtered and the filtrate concentrated. The crude product was purified by silica gel chromatography (24 g REDISEP column, eluting with 5% EtOAc in hexane). Fractions containing the product were combined and evaporated to afford Intermediate 314A as a white solid (2 g, 88%). 1H NMR (300 MHz, DMSO-d6) delta ppm 7.68-7.57 (m, 2H), 7.46-7.40 (m, 2H), 3.18 (s, 3H), 3.08 (s, 1H), 3.07 (s, 3H), 3.05-3.02 (m, 1H), 2.74-2.71 (m, 1H), 2.70-2.67 (m, 1H).

Statistics shows that 1,3-Dibromo-2,2-dimethoxypropane is playing an increasingly important role. we look forward to future research findings about 22094-18-4.

Reference:
Patent; Bristol-Myers Squibb Company; Velaparthi, Upender; Darne, Chetan Padmakar; Liu, Peiying; Wittman, Mark D.; Pearce, Bradley C.; Araujo, Erika M. V.; Dasgupta, Bireshwar; Nair, Jalathi Surendran; Janakiraman, Sakthi Kumaran; Rachamreddy, Chandrasekhar Reddy; Rao, Mettu Mallikarjuna; Karuppiah, Arul Mozhi Selvan Subbiah; Reddy, Bandreddy Subba; Nagalakshmi, Pulicharla; Bora, Rajesh Onkardas; Maheshwarappa, Shilpa Holehatti; Kumaravel, Selvakumar; Mullick, Dibakar; Sistla, Ramesh; (353 pag.)US9273058; (2016); B2;,
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Adding a certain compound to certain chemical reactions, such as: 645-36-3, name is 2,2-Diethoxyethanamine, 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 645-36-3, Computed Properties of C6H15NO2

N-(3-Bromo-4-chlorobenzyl)-2,2-diethoxyethanamine To a solution of 3-bromo-4-chlorobenzaldehyde (10.0 g, 45 mmol) and 2,2-diethoxyethanamine (6.68 g,50 mmol) in 200 mL of DCM at RT, 0.5 mL of AcOH was added and the resulting mixture was stirred at RT for 30 min. To this mixture, NaCNBH3 (8.1 g, 135 mmol) was added in portions and then stirred at RT overnight. The reaction mixture was portioned between water and DCM. The organic layer was washed with water (80 mL x 2) and brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo to afford the desired product (11 g, 72% yield) as an oil. The crude product obtained was used directly in the next step without further purification

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,2-Diethoxyethanamine, and friends who are interested can also refer to it.

Reference:
Patent; ARAXES PHARMA LLC; LI, Liansheng; FENG, Jun; WU, Tao; REN, Pingda; LIU, Yi; LIU, Yuan; LONG, Yun, Oliver; WO2015/54572; (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. 33311-29-4, name is 4-(2-Methoxyethoxy)aniline, A new synthetic method of this compound is introduced below., Safety of 4-(2-Methoxyethoxy)aniline

4-(2-Methoxyethoxy)aniline (500mg) was added to acetic anhydride (2.38g) and the mixture was cooled down to 10C. HN03 (65% in water, 0.62ml) was added slowly in order to keep the temperature of the reaction mixture below 15C. After the end of the addition, the reaction mixture was allowed to warm to RT over 1 h, was quenched with ice-cold water and stirred for 10min. The resulting suspension was filtered off and dried in high vacuo. The resulting yellow powder was dissolved in dioxane (1.4ml) , treated with 6N HCl (1 .4ml_) and the reaction mixture was stirred at 70C for 3h. After cooling down to RT, water was added and the pH was adjusted to 10 with 1 M NaOH. The layers were separated and the aq. phase was extracted with EA. The combined org. layers were washed with brine, dried (Na2SO4) and evaporated in vacuo to afford 303mg of yellow solid. LC-MS (B): tR = 0.99min; [M+H]+: 213.05.

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; ACTELION PHARMACEUTICALS LTD; CAROFF, Eva; KELLER, Marcel; KIMMERLIN, Thierry; MEYER, Emmanuel; WO2013/114332; (2013); A1;,
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Application of 52189-63-6, These common heterocyclic compound, 52189-63-6, name is 1-Fluoro-3,5-dimethoxybenzene, 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.

Weigh 1.5g of 1-fluoro-3,5-dimethoxybenzene and dissolve it with CH2Cl2.40 ml of BBr3/CH2Cl2 solution was added dropwise under ice bath, and reacted at room temperature overnight.After the end, the excess boron tribromide is quenched with methanol.Add ice water, stir, distill off most of the CH2Cl2 under reduced pressure, and extract the aqueous phase three times with ethyl acetate.The ethyl acetate layer was combined, dried with saturated brine, and EtOAc evaporated.The product was obtained in an amount of 1.2 g, which was used without further purification.

Statistics shows that 1-Fluoro-3,5-dimethoxybenzene is playing an increasingly important role. we look forward to future research findings about 52189-63-6.

Reference:
Patent; Cai Pei; Xiao Zuoqi; Ouyang Bo; Pan Tao; Zheng Yi; (7 pag.)CN109678915; (2019); A;,
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Related Products of 51344-14-0, 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. 51344-14-0, name is N,N-Dimethyl-2-(p-tolyloxy)ethanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

58.9 g (0.495 mol) of potassium bromide,Hydrogen peroxide 60 ml,Water 60 ml and 150 ml of chloroform were added to a liter of three bottles,Drop under ice bath32 ml concentrated sulfuric acid,Drop finished, remove the ice bath,Add 4- (2-dimethylaminoethoxy) toluene134 g (0.75 mol),The reaction solution was refluxed under light for 2 h,After completion of the reaction, the organic layer was separated, dried over anhydrous sodium sulfate, And the crude product was distilled under reduced pressure to give 185 g of a pale yellow liquid in a yield of 96%.

The synthetic route of N,N-Dimethyl-2-(p-tolyloxy)ethanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Anhui Cheng Lian Pharmaceutical Technology Co., Ltd.; Liu Hui; (5 pag.)CN106748821; (2017); 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. 768-70-7, name is 3-Ethynylanisole, This compound has unique chemical properties. The synthetic route is as follows., name: 3-Ethynylanisole

General procedure: To a stirred solution of alkyne (12mmol, 1.2equiv) in 50mL DCM was added copper(I)-thiophene-2-carboxylate (CuTc, 95mg, 0.5mmol, 0.05equiv). The solution was cooled to 0C and treated dropwise with a solution of 10mmol sulfonyl azide in 10mL DCM. Then, the reaction mixture was stirred a further 12h, monitored by TLC. After reaction, it was diluted with 30mL saturated NH4Cl and extracted with DCM (30mL¡Á3). The combined organics were washed with brine, dried with Na2SO4 and concentrated in vacuo. The crude product was then purified by flash chromatography (Petroleum ether/EtOAc=5:1-1:1). Subsequent recrystallization from EtOAc/Petroleum ether provided the title triazoles substrates.

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 768-70-7.

Reference:
Article; Meng, Jiang; Ding, Xiangfeng; Yu, Xingxin; Deng, Wei-Ping; Tetrahedron; vol. 72; 1; (2016); p. 176 – 183;,
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