Author: Jessica.F

Reference of 332-48-9,Some common heterocyclic compound, 332-48-9, name is 1-(2-Bromoethoxy)-4-fluorobenzene, molecular formula is C8H8BrFO, 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.

To a solution of diethyl but-3-en-1-ylmalonate (2.00 g, 9.3 mmol) in DMF was added NaH (448.0 mg, 11.2 mmol) at 0 C. The mixture was stirred at 0 C for 30 min. Then 1- (2- bromoethoxy) -4-fluorobenzene was added and the mixture was stirred at room temperature for 10.5 hr. The reaction mixture was quenched with water and the mixture was extracted with AcOEt. The organic layer was dried over Na2S04, filtered and evaporated. The crude product was purified by silica gel column chromatography (hexane: AcOEt = 200: 1 to 20: 1) to give the titled compound (2.2 g). ‘H NMR (CDC13) 8 : 7.00-6. 90 (m, 2H), 6.80-6. 76 (m, 2H), 5. 85-5. 67 (m, 1H), 5.07-4. 96 (m, 2H), 4.30-4. 20 (m, 4H), 4.05-3. 95 (m, 2H), 2.45-2. 40 (m, 2H), 2.15-1. 92 (m, 4H), 1.29-1. 15 (m, 6H) ppm.

The synthetic route of 332-48-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER JAPAN, INC.; PFIZER INC.; WO2005/80317; (2005); A2;,
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Synthetic Route of 54149-17-6, 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. 54149-17-6, name is 1-Bromo-2-(2-methoxyethoxy)ethane belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

According to the literature [39], we followed the N-alkylation reaction to carry out the synthesis of compound 3. A 100mL round bottom flask was charged with intermediate 2 (1mmol), 1-bromo-2-(2-methoxyethoxy)ethane (2.2mmol) and sodium hydroxide (4mmol) in acetonitrile (15mL). The reaction mixture was stirred at 80C overnight. After removing the solvent, the residue was dissolved in dichloromethane. The organic solution was washed with water three times and then dried over anhydrous magnesium sulfate. Purified by column chromatography on silica gel with gradient eluents of petroleum ether and ethyl acetate, the pure target compound 3 was afforded.

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-2-(2-methoxyethoxy)ethane, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Jiang, Kai; Chen, Si-Hong; Luo, Shi-He; Pang, Chu-Ming; Wu, Xin-Yan; Wang, Zhao-Yang; Dyes and Pigments; vol. 167; (2019); p. 164 – 173;,
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Application of 89282-70-2,Some common heterocyclic compound, 89282-70-2, name is 2-Methoxy-2-methylpropan-1-amine, molecular formula is C5H13NO, 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 5 N-(3-{[(2-methoxy-2-methylpropyl)amino]methyl}-8-methylquinolin-7-yl)-4-(tetrahydrofuran-2-ylmethoxy)benzamide monohydrochloride [Show Image] N-(3-Formyl-8-methylquinolin-7-yl)-4-(tetrahydrofuran-2-ylmethoxy)benzamide (1.0 g) obtained in Reference Example 2 and 2-methoxy-2-methylpropan-1-amine 0.5 oxalate (600 mg) were suspended in 1-methyl-2-pyrrolidone (10 mL) and acetic acid (5.0 mL) and the mixture was stirred at room temperature for 3 hr. Sodium triacetoxyborohydride (2.35 g) was added and the mixture was stirred at room temperature for 3 hr. 1N Aqueous sodium hydroxide solution was added to quench the reaction and basify the mixture. The mixture was partitioned and extracted with ethyl acetate, the organic layer was added to a solution of citric acid (4.0 g) in water (40 mL)-dimethyl sulfoxide (20 mL), and the mixture was washed with ethyl acetate. 1N Aqueous sodium hydroxide solution was added to the aqueous layer, and the mixture was partitioned and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained amorphous product was dissolved in ethyl acetate, and 4N hydrogen chloride-ethyl acetate solution (0.15 mL) was added. The obtained solid was recrystallized from ethyl acetate-methanol to give the title compound (101 mg, yield 8%) as a colorless solid. 1H NMR (300 MHz, DMSO-d6) delta: 1.20 (6 H, s), 1.68 – 1.72 (1 H, m), 1.87 – 1.90 (2 H, m), 1.96 – 2.00 (2 H, m), 2.68 (3 H, s), 2.97 – 3.00 (1 H, m), 3.11 (3 H, s), 3.68 – 3.81 (2 H, m), 4.02 – 4.06 (2 H, m), 4.16 – 4.20 (1 H, m), 4.42 (2 H, s), 7.09 (2 H, d, J=8.7 Hz), 7.75 (1 H, d, J=8.7 Hz), 7.90 (1 H, d, J=8.7 Hz), 8.04 (2 H, d, J=8.7 Hz), 8.72 (1 H, s), 9.20 (1 H, s), 9.27 (2 H, br), 10.25 (1 H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Methoxy-2-methylpropan-1-amine, its application will become more common.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2392573; (2011); 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. 5467-58-3, name is 1-Bromo-4-methoxynaphthalene, A new synthetic method of this compound is introduced below., SDS of cas: 5467-58-3

5-a. Synthesis of 1-methoxy-4-{3,5-(diphenyl)phenyl}naphthalene 1-Methoxy-4-{3,5-(diphenyl)phenyl}naphthalene was synthesized as follows. 1-Bromo-4-methoxynaphthalene (25 g, 0.105 mol), 3,5-diphenylphenylboronic acid 37.6 g (0.137 mol), potassium carbonate (21.9 g, 0.16 mol), tetrakis(triphenylphosphine)palladium(0) (2.4 g, 0.01 mol), water (25 mL), tetrahydrofuran (75 mL) and toluene (75 mL) were stirred in a 250 mL round-bottom flask for 12 hours under reflux. After completion of the reaction, the reaction mixture was cooled to room temperature and extracted with ethyl acetate (500 mL) and water (600 mL). The organic layer was dried with magnesium sulfate and concentrated under reduced pressure. The resulting solid was dissolved in hot toluene (1000 mL) and filtered. The filtrate was concentrated and recrystallized in methanol (800 mL). The resulting solid was filtered and washed with hexane (300 mL) to obtain a product (23.5 g, 0.061 mol, 57.6%).

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; SFC CO., LTD.; US2011/108827; (2011); A1;,
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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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