Month: February 2021

Reference of 59557-91-4, 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. 59557-91-4, name is 4-Bromo-2-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 99 7-[(cyclopropylmethyl)amino]-5-{ [2-methoxy-4-(piperidin-4-yl)phenyl]amino}pyrido[3,4- d]pyridazin-4-ol EXAMPLE 99A itri-buty l 4-(4-amino-3-methoxyphenyl)-5,6-dihvdropyridine- l (2/J)-carbox late A mixture of 4-bromo-2-methoxybenzenamine ( 1.21 g, 6.0 mmol), tert-butyl 4- (3,3,4,4-tetramethylborolan-l-yl)-5,6-dihydropyridine- l (2/ )-carboxylate ( 1 .95 g. 6.3 mmol), sodium carbonate (1.91 g, 18 mmol) and 1, 1 ‘- bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.22 g, 0.3 mmol) in dioxane (25 mL) and water (5 mL) was degassed with nitrogen and heated at 90C for 1 hours. After coohng to ambient temperature, the mixture was filtered, concentrated and purified by flash” chromatography eluting with 200: 1 dichloromethane/methanol to give the title compound.MS: 305 (M+rf).

The chemical industry reduces the impact on the environment during synthesis 4-Bromo-2-methoxyaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ABBOTT LABORATORIES; ABBOTT LABORATORIES TRADING (SHANGHAI) COMPANY, LTD.; VASUDEVAN, Anil; PENNING, Thomas Dale; CHEN, Huanming; LIANG, Bo; WANG, Shaohui; ZHAO, Zhongqiang; CHAI, Dikun; YANG, Leifu; GAO, Yingxiang; WO2012/97682; (2012); A1;,
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Reference of 64115-88-4,Some common heterocyclic compound, 64115-88-4, name is 1-Bromo-2-(trifluoromethoxy)benzene, molecular formula is C7H4BrF3O, 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.

n-Butyllithium (5.9 ml, 9.5 mmol) was added to a solution of 1-BROM-2- (trifluoromethoxy) benzene (2 g, 8.2 mmol) in tetrahydrofuran (28 ML) at-78C and stirred for 45 minutes. Triisopropyl borate (2. 58 ml, 11.1 mmol) was added dropwise to the reaction mixture and the solution was slowly brought to room temperature over 16 hours. The reaction mixture was quenched with water, made basic with 2N NAOH and extracted with ethyl acetate. The aqueous solution was acidified with 2N HCI, stirred for 1 hour at room temperature and extracted into ethyl acetate. The organic layer was washed with water, brine solution and dried over sodium sulfate. It was filtered and concentrated to give the product (1.10 g, 65%) as a white solid. &No.x0;HNMR (CDCL3) ( 8, ppm): 7.96 (dd, J= 7.2, 1.6 Hz, 1 H), 7.53 (ddd, J = 9.1, 7.3, 1. 8 HZ, 1 H), 7.38 (td, J = 7.3, 0.7 Hz, 1 H), 7.28 (d, J = 8.2 Hz, 1 H), 5.25 (br s, 2H). MS: m/e 206.9 (M+1) +.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-2-(trifluoromethoxy)benzene, its application will become more common.

Reference:
Patent; MERCK & CO., INC.; WO2004/92140; (2004); 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 768-70-7 as follows. Recommanded Product: 768-70-7

To a 35 mL microwave reaction tube were added Int-30f (500 mg, 1.36 mmol), bis(triphenylphosphine)palladium (II) dichloride (95 mg, 0.135 mmol), copper iodide (258 mg, 1.355 mmol), and DMF (10 mL). The resulting suspension was degassed and heated to 100 C, and then Int-31a was then added in portions via a syringe. The resulting mixture was allowed to stir at 100 C for additional 6 hours under nitrogen. After cooling, the solution was diluted with 10 mL of ethyl acetate, filtered, and concentrated in vacuo. The residue was purified using a 40 g silica column/Combi-Flask Rf system (0-15% ethyl acetate in hexanes eluent) to provide Int-31b as a wax (370 mg, 65%).

According to the analysis of related databases, 768-70-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KOZLOWSKI, Joseph A.; ROSENBLUM, Stuart B.; COBURN, Craig A.; SHANKAR, Bandarpalle, B.; ANILKUMAR, G., Nair; CHEN, Lei; DWYER, Michael, P.; JIANG, Yueheng; KEERTIKAR, Kartik, M.; LAVEY, Brian, J.; SELYUTIN, Oleg, B.; TONG, Ling; WONG, Michael; YANG, De-Yi; YU, Wensheng; ZHOU, Guowei; WU, Hao; HU, Bin; ZHONG, Bin; SUN, Fei; JI, Tao; SHEN, Changmao; RIZVI, Razia; ZENG, Qingbei; WO2012/41014; (2012); A1;,
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Reference of 32338-02-6,Some common heterocyclic compound, 32338-02-6, name is 2-Bromo-4-methoxyaniline, molecular formula is C7H8BrNO, 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 4 4-Methoxy-2-((trimethylsilyl)ethynyl)aniline (Compound 7) Compound 6 (1.40 g, 6.97 mmol), triphenylphosphine (55 mg, 3 mol percent) and copper (I) iodide (13 mg, 1 mol percent) were added to an oven-dried reaction flask containing toluene (27 mL) and Et3N (7 mL). The reaction mixture was stirred at room temperature for 5 min with N2 (g) bubbling. Bis(triphenylphosphine)palladium (II) dichloride (48 mg, 1 mol percent) and a solution of trimethylsilylacetylene (1.49 mL, 10.46 mmol) in Et3N (3 mL) were added. The reaction mixture was stirred at 100¡ã C. for 24 h. The reaction was cooled to room temperature, then diluted with EtOAc (300 mL) and washed with brine (3*70 mL). The organic layer was collected, dried over anhydrous Na2SO4, filtered, concentrated and purified by silica column chromatography (8percent EtOAc in hexanes) to afford compound 7 in 70.0percent (1.07 g) yield as a brown oil. 1H-NMR (CDCl3, 400 MHz) delta 6.81 (1H, s, Ar), 6.74 (1H, d, J=8.8 Hz, Ar), 6.63 (1H, d, J=8.8 Hz, Ar), 3.70 (3H, s, OCH3), 3.50 (2H, bs, NH2), 0.24 (9H, s, Si(CH3)3); 13C-NMR (CDCl3, 100 MHz) delta 151.7, 142.4, 117.7, 115.8, 115.6, 108.3, 101.7, 99.7, 55.7, 0.08; MS (ESI) m/z Calcd for C12H17NOSi (M+): 219.1, Found: 220.1 (M+H+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-4-methoxyaniline, its application will become more common.

Reference:
Patent; UNIVERSITY OF MARYLAND, BALTIMORE; FLETCHER, Steven; US2014/256817; (2014); A1;,
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Adding a certain compound to certain chemical reactions, such as: 450-88-4, name is 1-Bromo-4-fluoro-2-methoxybenzene, 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 450-88-4, Recommanded Product: 1-Bromo-4-fluoro-2-methoxybenzene

1-Bromo-4-fluoro-3-methoxybenzene (773 mg, 3.77 mmol) and bis(pinacolato)diboron (1.24 mg, 4.90 mmol) were dissolved in dioxane (10 mL), and anhydrous potassium acetate (1.11 mg, 11.31 mmol) and [1,1′-bis (diphenylphosphino)ferrocene]dichloropalladium.dichloromethane (276 mg, 0.377 mmol) were added. Under nitrogen gas atmosphere, the mixture was heated to 80 C. and stirred for 16 hours. After cooling to room temperature, the mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel TLC preparative plate (petroleum ether: ethyl acetate=1:1) to give compound 27-a (600 mg, yield 63%). 1H-NMR (400 MHz, CDCl3) delta: 7.65 (t, J=8.0 Hz, 1H), 6.55-6.66 (m, 2H), 3.82 (s, 3H), 1.34 (s, 12H) ppm

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, 1-Bromo-4-fluoro-2-methoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GUANGZHOU MAXINOVEL PHARMACEUTICALS CO., LTD.; XU, Zusheng; ZHANG, Nong; WANG, Tinghan; SUN, Qingrui; WANG, Yuguang; (90 pag.)US2018/208604; (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. 67191-35-9, name is 1-Isopropoxy-2-vinylbenzene, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 67191-35-9

The ruthenium complex of formula 1.2 (0.309 g; 0.344 mmol; 1 eq.) (also called [(5-cyclopentyl-2-mesityl)-imidazo-1-lidene]dichloro(3-phenyl-1H-inden-1-ylidene)(tricyclohexylphospine)ruthenium) was reacted with the styrenyl ether of formula 2H (65 mg; 0.37 mmol; 1.1 eq.). The reaction is carried out in the presence of dichloromethane (DCM; 3.5 mL) and copper(l) chloride (CuCl; 36.8 mg; 0.37 mmol; 1.1 eq.), at 35 C. for 5 hours.After purification on a silica gel column, the alkylidene ruthenium complex of formula 1.5 is obtained (89 mg; 0.158 mmol; 45%):in which Mes represents the mesityl group.The reaction scheme is shown below:In this reaction scheme, Cy3P represents tricyclohexylphosphine, Mes represents the mesityl group, and Ph represents a phenyl group.The scheme shows that the product obtained, at a yield of 45%, is the alkylidene ruthenium complex of formula 1.5.NMR1H (400 MHz, CDCl3): 16.42 (s, 1H); 7.50 (m, 1H); 7.27 (m, 1H); 7.10 (s, 2H); 7.01 (m, 1H); 6.95 (m, 2H); 6.88 (d, J=2 Hz, 1H); 5.96, (q, J=7.5 Hz, 1H); 5.18 (sept., J=6.21 Hz, 1H);13C (100 MHz, CDCl3): 172.2; 152.7; 144.5; 139.6; 137.6; 137.4; 129.3; 129.0; 125.0; 122.7; 122.4; 118.5; 113.0; 75.1; 64.2; 34.4; 24.7; 22.0; 21.4; 18.2.The alkylidene ruthenium complex of formula 1.5 was isolated and was submitted to various studies.

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 67191-35-9.

Reference:
Patent; ECOLE NATIONALE SUPERIEURE DE CHIMIE DE RENNES; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE CNRS; Mauduit, Marc; Rouen, Mathieu; US2015/315223; (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. 171290-52-1, name is 3,5-Dimethoxyphenylacetylene, A new synthetic method of this compound is introduced below., Quality Control of 3,5-Dimethoxyphenylacetylene

Formula 7 of the azide compound (300 mumol), alkynyl (750 mumol), CuSO4 (9.6 mg, 60 mumol) and Na. An ascorbate (60.0 mg, 300 mumol) 1: was dissolved in 1 t-BuOH / H2O (3 mL). The mixture was stirred at room temperature for 2 hours. After the reaction was completed, the mixture was filtered of and washed using H2O (70 mL) (solid A). The filtrate was extracted with EtOAc (3 ¡Á 70 mL). The combined organic extracts were then dried using anhydrous MgSO4, filtered and concentrated by rotaryevaporation (residue B). It was combined and the solid residue A and B, was purified by column chromatography to give the compound of formula 2 and 3. Formula 2 for the general method in accordance with, 1:1 t-BuOH/H2O (3 mL) in a compound 7a (95.8 mg, 300 mumol), 1-ethynyl -3,5-dimethoxybenzene (121 mg, 750 mumol), CuSO4 (9.6 mg, 60 mumol) and Na. Using ascorbate (60.0 mg, 300 mumol) was prepared in the desired compound. After stirring at room temperature the reaction mixture for 2 hours, was purified by column chromatography (5: 1 hexane / EtOAc ? 40: 1 CH2Cl2 / MeOH) to compound 2a using a was obtained as a brown solid (138 mg, 98%).

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

Reference:
Patent; EWHA UNIVERSITY INDUSTRY-ACADEMIC COOPERATION FOUNDATION; YOO, JAE SANG; SONG, DOO HUI; (33 pag.)KR2015/134731; (2015); A;,
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Electric Literature of 60789-54-0, These common heterocyclic compound, 60789-54-0, name is ((4-Bromobutoxy)methyl)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 231 4-Amino-5-chloro-2-methoxy-N-(piperidin-4-ylmethyl)benzamide dihydrochloride (1.1 g) as starting compound, potassium carbonate (1.5 g) and 4-benzyloxybutyl bromide (1.0 g) were reacted and treated in the same manner as in Example 168 to give 0.32 g of 4-amino-5-chloro-2-methoxy-N-((1-(4-benzyloxybutyl)piperidin-4-yl)methyl)benzamide. 1 H-NMR (CDCl3,ppm) delta: 1.40-1.81(9 H,m), 2.82(2 H,t), 2.98(2 H,t), 3.20(2 H,t), 3.44(4 H,m), 3.82(3 H,s), 4.45(3 H,s), 5.93(2 H,s), 6.48(1 H,s), 7.33-7.45(5 H,m), 7.66(1 H,s), 8.00(1 H,t)

The synthetic route of 60789-54-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Yoshitomi Pharmaceutical Industries, Ltd.; US5864039; (1999); A;,
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Related Products of 5467-58-3,Some common heterocyclic compound, 5467-58-3, name is 1-Bromo-4-methoxynaphthalene, molecular formula is C11H9BrO, 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.

Under a nitrogen atmosphere, into a 250 mL three-necked flask equipped with a magnetic stirrer, a thermometer, and a condenser, 6.6 g (27.9 mmol) of 1-bromo-4-methoxynaphthalene and 12.0 g (36.3 mmol) of 4- were added. Nitrophenyl-2-amino-9,9-dimethylhydrazine,10.6g (167.4mmol) of copper powder, 23.1g (167.4mmol) of potassium carbonate, 7.4g (27.9mmol) of 18-crown-6, then add 57.2ml of o-dichlorobenzene, react at 170 C for 20h; Filtration, distillation of o-dichlorobenzene under reduced pressure, and the obtained crude product was ethanolRecrystallization with N,N-dimethylacetamide (V:V = 1:2.7),4-nitrophenyl-4′-methoxynaphthyl-2-amino-9,9-dimethylfluorene 10.2 g, yield 75%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-4-methoxynaphthalene, its application will become more common.

Reference:
Patent; Jilin University; Chen Chunhai; Su Kaixin; Wang Daming; Sun Ningwei; Zhou Hongwei; Zhao Xiaogang; (23 pag.)CN108912003; (2018); A;,
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Synthetic Route of 41365-75-7, 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. 41365-75-7, name is 1-Amino-3,3-diethoxypropane, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 4-(chloromethyl)-benzoyl chloride (1.17 g, 6.21 mmol) in DCM (10 mE) was added a solution of 3,3-diethoxypropan-1-amine (0.914 g, 6.21 mmol) and triethylamine (1.04 mE, 7.77 mmol) in DCM (10 mE). The reaction mixture was stirred at room temperature for 3 hours. The solvent was evaporated under reduced pressure and the residue dissolved in ethyl acetate. The organic phase was washed with 1 M aqueous sodium hydroxide, brine and dried over anhydrous magnesium sulfate and the filtrate was evaporated under reduced pressure to afford the title compound(1.83 g, 99%). 1H NMR (400 MHz, DMSO-d5); oe 8.45 (dd, J=5.5,5.5 Hz, 1H), 7.83 (d, J=8.4 Hz, 2H), 7.52 (d, J=8.3 Hz, 2H),4.81 (s, 2H), 4.56 (dd, J=5.5, 5.5 Hz, 1H), 3.59 (ddd, J=7.1,9.5, 14.1 Hz, 2H), 3.45 (ddd, J=7.1, 9.5, 14.1 Hz, 2H), 3.29 (dd, J=6.0, 7.4 Hz, 2H), 1.79 (dd, J=6.4, 13.6 Hz, 2H), 1.12 (dd, J=7.0, 7.0 Hz, 6H).

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

Reference:
Patent; CHIESI FARMACEUTICI S.p.A.; RANCATI, Fabio; RIZZI, Andrea; CARZANIGA, Laura; LINNEY, Ian; KNIGHT, Chris; SCHMIDT, Wolfgang; (176 pag.)US2016/235734; (2016); A1;,
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