Month: September 2021

Electric Literature of 3401-47-6, A common heterocyclic compound, 3401-47-6, name is 1-Bromo-2-methoxynaphthalene, molecular formula is C11H9BrO, 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.

[Step 1] Synthesis of 1-(2-Fluorophenyl)-2-methoxynaphthalene Into a 500 mL three-neck flask were placed 8.7 g (35 mmol) of 1-bromo-2-methoxynaphthalene, and 5.0 g (35 mmol) of 2-fluorophenylboronic acid. The air in the flask was replaced with nitrogen. To this mixture were added 120 mL of toluene, 60 mL of ethanol, and 40 mL of an aqueous solution of sodium carbonate (2.0 mol/L). While the pressure was reduced, this mixture was stirred to be degassed. To this mixture was added 2.0 g (1.7 mmol) of tetrakis(triphenylphosphine)palladium(0), and the mixture was stirred at 80 C. for 8 hours under a nitrogen stream. The aqueous layer of the obtained mixture was subjected to extraction with toluene, and the obtained solution of the extract and the organic layer were combined and washed with saturated brine. The organic layer was dried with magnesium sulfate, and this mixture was gravity-filtered. An oily substance obtained by concentration of the obtained filtrate was dissolved in about 30 mL of toluene. This solution was suction-filtered through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), alumina, and Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135). An oily substance obtained by concentration of the obtained filtrate was dried under reduced pressure, so that 5.3 g of a pale yellow oily substance of the object of the synthesis was obtained in 60% yield. The reaction scheme of Step 1 is illustrated in (E2-1).

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; Semiconductor Energy Laboratory Co., Ltd.; US2012/165550; (2012); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

588-96-5, A common heterocyclic compound, 588-96-5, name is p-Bromophenetole, molecular formula is C8H9BrO, 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.

General procedure: b.Cyanation of aryl bromides. To a solution of arylbromide (0.5 mmol) in EtOH (5.0 mL) was added NCTS (272 mg, 1.0 mmol), PdCl2 (13.3 mg, 0.075 mmol), and Ag2O (57.75 mg, 0.5 mmol). The mixture was stirred at 70 for 24 hunder air atmosphere. Then the reaction mixture was cooled to room temperature and filtered through a pad of celite (1.0 g) and rinsed with CH2Cl2 (10.0 mL). The resulting organic solution was concentrated under reduced pressure and further purified by flash chromatography (SiO2,petroleum ether/EtOAc gradient), yielding the corresponding aryl nitriles.

The synthetic route of p-Bromophenetole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Li, Jizhen; Xu, Wenbin; Ding, Junshuai; Lee, Kuo-Hsiung; Tetrahedron Letters; vol. 57; 11; (2016); p. 1205 – 1209;,
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Application of 39021-83-5, These common heterocyclic compound, 39021-83-5, name is 1,4-Dimethoxy-2,3-dimethylbenzene, 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.

2-(bromomethyl)-1,4-dimethoxy-3-methylbenzeneInto a 50-mL round-bottom flask, was placed a mixture of 1,4-dimethoxy-2,3-dimethylbenzene (1.00 g, 6.02 mmol, 1.00 equiv)(Example 128), CCl4 (20 mL), NBS (1.20 g, 6.74 mmol, 1.10 equiv) and BPO (145 mg, 0.57 mmol, 0.10 equiv). The solution was stirred for 16 h at 80 C. After concentration, the residue was diluted with 50 mL of TBME and washed with 3×20 mL of brine. The organic phase was dried over anhydrous Na2SO4 and concentrated under reduced pressure. This resulted in 1.20 g (81%) of 2-(bromomethyl)-1,4-dimethoxy-3-methylbenzene as a brown crude solid.

Statistics shows that 1,4-Dimethoxy-2,3-dimethylbenzene is playing an increasingly important role. we look forward to future research findings about 39021-83-5.

Reference:
Patent; Global Blood Therapeutics, Inc.; Li, Zhe; Xu, Qing; Yu, Chul; Yee, Calvin; Gwaltney,, II, Stephen L.; Metcalf, Brian W.; Richards, Steven; Lardy, Matthew A.; Setti, Lina; Sham, Hing; US2015/315198; (2015); A1;,
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These common heterocyclic compound, 1516-96-7, name is 5-Bromo-1,3-di-tert-butyl-2-methoxybenzene, 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. Recommanded Product: 1516-96-7

A -78 C. solution of 5-bromo-1,3-di-tert-butyl-2-methoxybenzene (2.142 g; 7.158 mmol) in dry THF (15 mL) was treated with n-butyllithium (7.00 mL, 1.13M in hex, 7.88 mmol). The solution was stirred at -78 C. for 15 min, then treated with trimethylborate (976 muL; 8.59 mmol). The reaction was allowed to warm to ambient temperature and evaporated to a thick oil.

The synthetic route of 5-Bromo-1,3-di-tert-butyl-2-methoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Adams, Alan D.; Santini, Conrad; US2009/30012; (2009); A1;,
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Related Products of 171290-52-1,Some common heterocyclic compound, 171290-52-1, name is 3,5-Dimethoxyphenylacetylene, molecular formula is C10H10O2, 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 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 × 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. Following the general method for the general formula 2, 1: 1 t-BuOH / H2O (3 mL) in a compound 7e (29.5 mg, 100 mumol),1-ethynyl -3,5-dimethoxy-benzene (40.6 mg, 250 mumol), CuSO4 (3.2 mg, 20 mumol) and Na. ascorbate (20.0 mg, 100mumol) theOf the desired compound was prepared using. After stirring at room temperature the reaction mixture for 66 hours, was purified by column chromatography (5: 1 hexane / EtOAc ? 30: 1 CH2Cl2 / MeOH) Compound 2e by using as a brown solid form (23.1mg, 51%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,5-Dimethoxyphenylacetylene, its application will become more common.

Reference:
Patent; EWHA UNIVERSITY INDUSTRY-ACADEMIC COOPERATION FOUNDATION; YOO, JAE SANG; SONG, DOO HUI; (33 pag.)KR2015/134731; (2015); A;,
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Application of 349-65-5, A common heterocyclic compound, 349-65-5, name is 2-Methoxy-5-(trifluoromethyl)aniline, molecular formula is C8H8F3NO, 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.

According to Method C4, 2-methoxy-5-(trifluoromethyl)aniline was reacted with phosgene followed by 3-(-2-(N-methylcarbamoyl)-4-pyridyloxy)aniline to afford the urea. Entry 12: 4-Chloropyridine-2-carbonyl chloride HCl salt was reacted with ammonia according to Method A2, Step 3b to form 4-chloro-2-pyridinecarboxamide.

The synthetic route of 349-65-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Riedl, Bernd; Dumas, Jacques; Khire, Uday; Lowinger, Timothy B.; Scott, William J.; Smith, Roger A.; Wood, Jill E.; Monahan, Mary-Katherine; Natero, Reina; Renick, Joel; Sibley, Robert N.; US2001/11135; (2001); A1;; ; Patent; BAYER CORPORATION; US2002/165394; (2002); A1;; ; Patent; BAYER CORPORATION; US2003/181442; (2003); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 13468-02-5, name is N,N-Dimethyl-2-phenoxyethanamine, A new synthetic method of this compound is introduced below., Recommanded Product: 13468-02-5

The N, N – dimethyl – N – [(2 – phenoxy) ethyl] amine (1.65 g, 10 . 00 mmol) dissolved in dichloromethane (10 ml) in, under ice bath slowly […] sulfonic acid (2.5 ml The system for the ice in the pouring, adding dichloromethane (50 ml), separating the organic layer, drying with anhydrous sodium sulfate, concentrated under reduced pressure to obtain the crude intermediate 6 a, directly Used for the next step reaction.

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; Chengdu Xiandao Pharmaceutical Development Co., Ltd.; Li Jin; Wang Wei; Chu Hongzhu; Lv Kaizhi; Liu Lichuan; Nong Yunhong; Chen Wei; (17 pag.)CN110256416; (2019); A;,
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Synthetic Route of 458-52-6, These common heterocyclic compound, 458-52-6, name is 2-Fluoro-4-methoxyaniline, 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.

Step A 2-Fluoro-4-methoxyphenyl isocyanate To a solution of 13.75 g (0.0967 mole) of 2-fluoro-4-methoxyaniline in 120 mL of toluene was slowly added over a period of 30 minutes a solution of 19.13 g (0.0967 mole) of trichloromethyl chloroformate in 30 mL of toluene. During the addition the temperature rose to 35° C. The reaction mixture was stirred without external heating for 30 minutes and then heated at reflux for approximately 17 hours. At the end of this time all of the solvent was removed by distillation, leaving 2-fluoro-4-methoxyphenyl isocyanate as a purple liquid, which was used immediately in Step B.

The synthetic route of 458-52-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FMC Corporation; US5344812; (1994); A;; ; Patent; Theodoridis; George; US5798316; (1998); A;,
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Ether | (C2H5)2O – PubChem

Electric Literature of 38336-04-8, 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. 38336-04-8, name is 2-(Benzyloxy)-1-ethanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To 6-(1-((tert-butoxycarbonyl)amino)-2-ethoxy-2-oxoethyl)-5-fluoronicotinic acid 0.95 g (2.78 mmol) in dichloromethane (13 mL) was added triethylamine 1.15 mL (8.33 mmol, 3 eq), N-(3- dimethylaminopropyl)-N¢-ethylcarbodiimide hydrochloride 0.59 g (3.05 mmol, 1.1 eq), 1- hydroxybenzotriazole hydrate 0.41 g (3.06 mmol, 1.1 eq), followed by 2-(benzyloxy)ethan-1-amine ) 0.5 mL (3.33 mmol, 1.2 eq) and the reaction was stirred at RT for 18 h. The mixture was diluted with dichloromethane, washed with water/brine, dried over sodium sulfate and concentrated. The product was purified by flash chromatography on silica gel (30% ethyl acetate/hexanes) to afford the title compound. ESI-MS m/z 476 (MH)+.

The synthetic route of 2-(Benzyloxy)-1-ethanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VENATORX PHARMACEUTICALS, INC.; BURNS, Christopher J.; DAIGLE, Denis; CHU, Guo-Hua; HAMRICK, Jodie; BOYD, Steven A.; ZULLI, Allison L.; MESAROS, Eugen F.; CONDON, Stephen M.; TROUT, Robert E. Lee; MYERS, Cullen L.; XU, Zhenrong; (327 pag.)WO2019/226931; (2019); A1;,
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These common heterocyclic compound, 143-24-8, name is 2,5,8,11,14-Pentaoxapentadecane, 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. Quality Control of 2,5,8,11,14-Pentaoxapentadecane

Comparative Example 1 was conducted in the same manner as in Example 1 except that 4 mmole of 3-hydroxypyridine was used as promoter instead of imidazole and except the reaction conditions. 1 mmole of Co2(CO)8 was used and 200 mmole of ethylene oxide was used. The reaction conditions of Comparative Example 1 were shown in Table 2.

The synthetic route of 2,5,8,11,14-Pentaoxapentadecane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Samsung Electronics Co. Ltd.; US6348632; (2002); B1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem