Tag: M.W=200-300

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 18800-30-1 as follows. Safety of 1-Bromo-4-(2-bromoethoxy)benzene

General procedure: HBr (aq. 40%, 0.02 mol and 2.60 mL) was dropwise added to a solution of piperazidine (0.02 mol) in EtOH (50 mL) at r.t., and then 3a-3r (0.01 mol) in EtOH (50 mL) was added. The mixture was refluxed for 48 h, filtered and concentrated. The residue was dissolved in water, acidified with 10% HCl aq. to pH = 5-6 and washed with CH2Cl2, water layer was basified by 10-50 % NaOH till pH > 9 and extracted with CH2Cl2, dried over NaSO4 and evaporated until dryness to obtain the compounds 4a-4r with colorless oil in 35.24-70.98 % yields.

According to the analysis of related databases, 18800-30-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Guo, Xiaoke; Ma, Xianglei; Yang, Qian; Xu, Jing; Huang, Lu; Jia, Jianmin; Shan, Jiaojiao; Liu, Li; Chen, Weilin; Chu, Hongxi; Wei, Jinlian; Zhang, Xiaojin; Sun, Haopeng; Tang, Yiqun; You, Qidong; European Journal of Medicinal Chemistry; vol. 81; (2014); p. 89 – 94;,
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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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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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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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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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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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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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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 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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Related Products of 38197-43-2, 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 38197-43-2 as follows.

To a solution of 2-bromo-1-methoxy-3-methylbenzene (Combi-Blocks CAS No.38197-43-2) (1.024 g, 5.09 mmol) in tetrahydrofuran (25.5 mL) was added bis(dibenzylideneacetone)palladium (0.059 g, 0.102 mmol) and Q-Phos (1,2,3,4,5-Pentaphenyl-1′-(di-tert-butylphosphino)ferrocene) (pentaphenyl(di-tert-butylphosphino)ferrocene, 0.072 g, 0.102 mmol). Nitrogen was bubbled through the solution for about 3 minutes, then a 0.4 M in tetrahydrofuran solution of (1-(methoxycarbonyl)cyclopropyl)zinc(II) bromide (25.5 mL, 10.19 mmol) was added dropwise over 5 minutes and the internal temperature rose from 23.5 C. to 24.8 C. The reaction was stirred for 15 hours at ambient temperature, at which point it was quenched with saturated aqueous ammonium chloride (30 mL), diluted with methyl tert-butyl ether (130 mL), and the layers were separated. The organic layer was filtered through a pad of silica gel. The filtrate was concentrated in vacuo to give a crude residue that was purified via flash chromatography, eluting on a 40 g silica gel cartridge with 1-40% ethyl acetate/heptanes over 40 minutes to provide the title compound. 1H NMR (400 MHz, CDCl3) delta ppm 7.15 (t, J=7.9 Hz, 1H), 6.76-6.80 (m, 1H), 6.73 (d, J=8.2 Hz, 1H), 3.80 (s, 3H), 3.60 (s, 3H), 2.32 (s, 3H), 1.71-1.75 (m, 2H), 1.54 (s, 2H)+ MS (ESI+) m/z 221 (M+H)+, 243 (M+Na)+.

According to the analysis of related databases, 38197-43-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AbbVie S.a.r.l.; Galapagos NV; Altenbach, Robert J.; Bogdan, Andrew; Couty, Sylvain; Desroy, Nicolas; Gfesser, Gregory A.; Housseman, Christopher Gaetan; Kym, Philip R.; Liu, Bo; Mai, Thi Thu Trang; Malagu, Karine Fabienne; Merayo Merayo, Nuria; Picolet, Olivier Laurent; Pizzonero, Mathieu Rafael; Searle, Xenia B.; Van der Plas, Steven Emiel; Wang, Xueqing; Yeung, Ming C.; (189 pag.)US2019/77784; (2019); A1;,
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