Month: October 2020

74137-36-3, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 74137-36-3 name is 1,3-Dibromo-5-methoxybenzene, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: 3-Bromo-5-methoxy-1 ,1 ‘-biphenyl was synthesised according to general procedures GP13 – from 1 ,3- dibromo-5-methoxybenzene (6.50 g, 24.4 mmol), phenylboronic acid (2.08 g, 17.0 mmol), Pd(PPh3)4 (1 .40 g, 5 molpercent), Na2C03 (6.47 g, 61 .0 mmol), toluene (70 ml_), ethanol (7.0 mL) and water (7.0 ml_); 100 ¡ãC, 16 h. Chromatographic purification (hexane) afforded a colourless oil (4.1 g, contained a small amount of impurity), which is used in the subsequent transformation as an impure mixture. H NMR of a pure chromatography fraction (400 MHz, DMSO-c/6) delta: 7.55-7.53 (m, 2H), 7.43-7.42 (m, 2H), 7.37 (d, J = 7.3 Hz, 1 H), 7.32-7.31 (m, 1 H), 7.03 (d, J = 1 .4 Hz, 2H), 3.85 (s, 3H). General procedures GP13 [00693] A mixture of bromide GP13_1 , Pd(PPh3)4, ArB(OR’)2, Na2C03, H20, EtOH and toluene was degassed with argon and then stirred at 100 ¡ãC for 16 h. After cooling to rt, the mixture was diluted with Et20 and filtered through celite. The organic solution was washed with H20, dried over Na2S04, filtered and the solvent was removed under reduced pressure. The crude was purified by chromatography to afford biaryl GP13_2.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,3-Dibromo-5-methoxybenzene, and friends who are interested can also refer to it.

Reference:
Patent; THE INSTITUTE OF CANCER RESEARCH: ROYAL CANCER HOSPITAL; SPRINGER, Caroline; MARAIS, Richard; NICULESCU-DUVAZ, Dan; LEUNG, Leo; SMITHEN, Deborah; CALLENS, Cedric; TANG, Haoran; (403 pag.)WO2017/141049; (2017); A1;,
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70627-52-0, Adding a certain compound to certain chemical reactions, such as: 70627-52-0, name is N-(4-(Benzyloxy)benzylidene)-4-fluoroaniline, 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 70627-52-0.

Example 10 Process for the Preparation of 3-[5-Benzyloxy-2-[(4-benzyloxy-phenyl)-(4-fluoro-phenylamino)-methyl]-5-(4-fluoro-phenyl)-pentanoyl]-4-phenyl-oxazolidin-2-one 18 ml of Dichloromethane was added to 2.1 ml of TiCl4 at 20-25 C. under nitrogen atmosphere Cooled the reaction mass to 0 C., 2 ml of Ti(O-ipr)4 was added and stirred for about 15 minutes. To the reaction mass 50 ml Dichloromethane, 10 gms of 1-[5-Benzyloxy-5-(4-fluoro-phenyl)-pentanoyl]-5-phenyl-pyrrolidin-2-one and 13.7 gms of Imines were added at 20-25 C. under nitrogen atmosphere. The reaction mass was cooled -30to -35 C. and 5.8 gms of Diisopropyl ethyl amine was added. Stirred the reaction mass for about 15 minutes and TiCl4 solution was added. Stirred the reaction mass for about 2-3 hours at -30to -35 C. and 60 ml of isopropyl alcohol was added followed by 50 ml of Dichloromethane and stirred the reaction mass for about 60 minutes, 6% Tartaric acid solution was added to the reaction mass at 20-25 C. and stirred for about 2 hours. Separate the organic layer and extract the reaction mass with 100 ml of dichloromethane. Combined the organic layers and washed with H2O followed by brine solution. Separated the organic layer and dried over Sodium Sulfate. Distilled the solvent completely under reducing pressure at 50-55 C. and 500 ml of methanol was added. Stirred the reaction mass for about 1-2 hours at 20-25 C., filtered the compound, washed with methanol and dried at 60-65 C. to get 8 gms of 3-[5-Benzyloxy-2-[(4-benzyloxy-phenyl)-(4-fluoro-phenylamino)-methyl]-5-(4-fluoro-phenyl)-pentanoyl]-4-phenyl-oxazolidin-2-one.

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, N-(4-(Benzyloxy)benzylidene)-4-fluoroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Mylan Laboratories Limited; Husain, Mofazzal; G.S.C., Srikanth; Thorpunuri, Swapna; Datta, Debashish; (11 pag.)US2016/280642; (2016); A1;,
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A common compound: 1484-26-0, name is 3-Benzyloxyaniline, belongs to ethers-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 1484-26-0

General procedure: BSB-Cl 2 (314 mg, 1.2 mmol) and aniline 1 (1mmol) were premixed in THF (10 ml) at0 C to which was added LiHMDS (2 ml, 2 mmol). The resulting mixture was stirred for2 h at this temperature. Upon reaction completion, the solution was concentrated. Theresidue was purified with basic alumina flash chromatography to afford pure product

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, 1484-26-0, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Lu, Erhu; Yadav, Arun; Weaver, Donald F.; Reed, Mark A.; Synlett; vol. 24; 17; (2013); p. 2259 – 2262;,
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Some common heterocyclic compound, 1484-26-0, name is 3-Benzyloxyaniline, molecular formula is C13H13NO, 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. 1484-26-0

A mixture of triethyl orthoformate (92 milliliters (mL), 0.55 mole (mol)) and 2,2-dimethyl-[1,3]-dioxane-4,6-dione (75.3 g, 0.522 mol) (Meldrum’s acid) was heated at 55¡ã C. for 90 minutes and then cooled to 45¡ã C. A solution of 3-benzyloxyaniline (100.2 g, 0.5029 mol) in methanol (200 mL) was slowly added to the reaction over a period of 45 minutes while maintaining the reaction temperature below 50¡ã C. The reaction was then heated at 45¡ã C. for one hour, allowed to cool to room temperature, and stirred overnight. The reaction mixture was cooled to 1¡ã C., and the product was isolated by filtration and washed with cold ethanol (400 mL) until the filtrate was colorless. 5-{[(3-benzyloxy)phenylimino]methyl}-2,2-dimethyl-[1,3]-dioxane-4,6-dione (170.65 g) was isolated as a tan, powdery solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1484-26-0, its application will become more common.

Reference:
Patent; Zarraga, Isidro Angelo E.; US2007/166384; (2007); A1;,
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29578-83-4, A common compound: 29578-83-4, name is 1-Bromo-3-methoxy-5-methylbenzene, belongs to ethers-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

). 1-Bromo-3-methoxy-5-methylbenzene (1.00 g, 5.0mmol) and pyridine/H2O (2:5, 30 mL) were added to a round-bottomflask, followed by KMnO4 (3.14 g, 20 mmol). The resulting mixturewas then heated while refluxing for 48 hr. After the removal of the precipitateby filtration, 2 M HCl was added to the reaction mixture to acidify it (pH 2).The aqueous phase was extracted with ethyl acetate. The organic phase waswashed with brine and dried over anhydrous Na2SO4. Thesolvent was removed under reduced pressure and the residue was purified usingsilica gel column chromatography. The white solid (385 mg, 34% yield) wasidentified as 3-bromo-5-methoxybenzoic acid (3a) on the basis of 1H-NMR spectra. 1H-NMR(400 MHz, CDCl3): d3.86(s, -OCH3, 3H), 7.29 (t, J=2.0Hz, Ar H, 1H), 7.54 (t, J=2.0 Hz, ArH, 1H), 7.83 (t, J=2.0 Hz, Ar H, 1H).

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-3-methoxy-5-methylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Ohe, Tomoyuki; Umezawa, Ryutaro; Kitagawara, Yumina; Yasuda, Daisuke; Takahashi, Kyoko; Nakamura, Shigeo; Abe, Akiko; Sekine, Shuichi; Ito, Kousei; Okunushi, Kentaro; Morio, Hanae; Furihata, Tomomi; Anzai, Naohiko; Mashino, Tadahiko; Bioorganic and Medicinal Chemistry Letters; vol. 28; 23-24; (2018); p. 3708 – 3711;,
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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. 3616-56-6, name is 2,2-Diethoxy-N,N-dimethylethanamine, A new synthetic method of this compound is introduced below., 3616-56-6

Synthesis example B17: Synthesis of 8-bromo-12H-benzofuranyl[2,3-a]carbazole (compound 17); (1 7); Under nitrogen, compound 16 (4.6 g, 1 eq) is initially charged and dissolved with acetic acid (185 ml) while heating to reflux. Then (dimethylamino)acetaldehyde diethyl acetal (95percent; 25 g, 10 eq.) is added dropwise to the reaction within 1 h and the mixture is stirred at reflux for 7 h. The mixture is cooled to room temperature and diluted with methylene chloride. In a separating funnel, the organic phase is washed with distilled water and then with saturated NaCI solution. The organic phase is dried with sodium sulfate and concentrated. LC (reverse phase, acetonitrile) gives 1 .35 g of product (27.3percent yield).1 H N MR (CD2CI2; 400 MHz): “5 = 8.73 (s, 1 H), 8.17 (s, 1 H), 8.16 (d, 1 H), 8.08 (d, 1 H), 7.78 (d, 1 H), 7.60 (d, 1 H), 7.56 (m, 2H), 7.49 (dd, 1 H), 7.31 (dd, 1 H).

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; BASF SE; BASF (CHINA) COMPANY LIMITED; KONINKLIJKE PHILIPS ELECTRONICS N.V.; OSRAM OPTO SEMICONDUCTORS GMBH; PHILIPS INTELLECTUAL PROPERTY & STANDARDS GMBH; LANGER, Nicolle; SCHILDKNECHT, Christian; WATANABE, Soichi; FUCHS, Evelyn; WAGENBLAST, Gerhard; LENNARTZ, Christian; MOLT, Oliver; DORMANN, Korinna; HUNZE, Arvid; KRAUSE, Ralf; SCHMID, Guenter; HEUSER, Karsten; VAN ELSBERGEN, Volker; BOERNER, Herbert Friedrich; WO2011/125020; (2011); A1;,
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Some common heterocyclic compound, 929-75-9, name is 1,11-Diamino-3,6,9-trioxaundecane, molecular formula is C8H20N2O3, 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. 929-75-9

General procedure: A mixture of cinnamic acid (6.30 mmol), EDCI (7.50 mmol), DMAP (0.60 mmol), and anhydrous dichloromethane (20 mL) was stirred to dissolve, then diamino-ether (3 mmol) was added and stirred at room temperature for 12 h. Then, the solid was filtered off, the filtrate was added with H2O (50 mL) and extracted by dichloromethane three times. The combined organic layers were washed with H2O and brine, dried with anhydrous sodium sulfate for 8 h, filtered, and evaporated. The resulting residue was purified by preparative TLC with petroleum ether/ethyl acetate = 2:1-1:1 to give pale white solid or light yellow oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 929-75-9, its application will become more common.

Reference:
Article; Wang, Jiawen; Hong, Ge; Li, Guoliang; Wang, Wenzhi; Liu, Tianjun; Molecules; vol. 24; 24; (2019);,
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946-80-5, 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. 946-80-5, name is Benzyl Phenyl Ether belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To 45 mL of the reaction tube were added 0.5 mmol of benzyl phenyl ether, 0.25 mmol of I2, 1.5 mL of acetonitrile solution of nitrosonium tetrafluoroborate (1.5 mL of solution containing 0.1 mmol of nitrosonium tetrafluoroborate), a sealed reaction tube , The temperature was controlled at 30 C, and the reaction was carried out under magnetic stirring for 5 hours, followed by cooling the reaction system to room temperature. The reaction mixture was purified by column chromatography to give 4-benzyloxyiodobenzene with an isolation yield of 60%. The structure of the product was determined using 1H-NMR, 13C-NMR, and GC-MS, see Figures 15-17

The synthetic route of 946-80-5 has been constantly updated, and we look forward to future research findings.

Reference:
Ether – Wikipedia,
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54149-17-6, name is 1-Bromo-2-(2-methoxyethoxy)ethane, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. 54149-17-6

(2S,6R, I lR)-6,l l -dimethyl-l-oxo- l ,2,3,4,5,6-hexahydro-2,6-methanobenzo[d]azocin-8-y trifluoromethanesulfonate hydrochloride (120 mg, 0.33 mmol), Cs2C03 (214.9 mg, 0.6494 mmol) and mPEG2-Br (78.45 mg, 0.4286 mmol) were dissolved in acetonitrile. The mixture was heated to 75 C for 16 h and cooled to room temperature. The mixture was concentrated under vacuum and purified by flash chromatography to yield (2S,6R,l lR)-8-hydroxy-3-(2- (2-methoxyethoxy) ethyl)-6,l l-dimethyl-3,4,5,6-tetrahydro-2,6-methanobenzo[d]azocin- l(2H)-one (14) (51.5 mg, 47% yield). NMR (500 MHz, CDC13): delta 8.02 (d, 1 H), 6.85 (m, 2H), 4.21-4.23 (m, 2H), 3.89 (t, 2H), 3.57-3.59 (m, 2H), 3.39 (s, 3H), 3.27 (d, 1H), 2.72-2.75 (m, 1 H), 2.55-2.61 (m, 1 H), 2.08-2.13 (m, 1H), 1.87-1.94 (m, 1H), 1.45-1.48 (m, 1H), 1.41 (s, 3H), 0.85 (d, 3H); MS (ESI) for C19H27N04: 334.1965 (MH+). The free base was dissolved in 4M hydrochloride in 2-propanol. The mixture was concentrated to afford product as hydrochloride salt.

Statistics shows that 54149-17-6 is playing an increasingly important role. we look forward to future research findings about 1-Bromo-2-(2-methoxyethoxy)ethane.

Reference:
Patent; NEKTAR THERAPEUTICS (INDIA) PVT.LTD.; NEKTAR THERAPEUTICS (Incorporated under the Laws of Delaware and domiclled in the State of California); DUARTE, FRANCO; ANAND, NEEL; SHARMA, PANKAJ; SINGH, DEVENDRAPRATAP U.; WO2015/79459; (2015); A1;,
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75148-49-1, These common heterocyclic compound, 75148-49-1, name is 3-Bromobenzaldehyde Diethyl Acetal, 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.

To a mixture of 3-bromobenzaldehyde diethylacetal (1.495 g, 5.77 mmol) and bis(triphenylphoshine)palladium(II) dichloride (206 mg, 0.29 mmol) in dimethoxyethane (30 mL) at room temperature under nitrogen, 2-thiopheneboronic acid (1.189 g, 9.29 mmol) and aquesou sodium bicarbonate (1M, 29 mL) were added. The mixture was heated to reflux overnight, cooled to room temperature, and diluted with ethyl acetate. The organic layer was washed with water and brine, dried over magnesium sulfate, filtered, and concentrated. The residue was purified by silica gel chromatography to give a mixture of 2-(3-(diethoxymethyl)phenyl)thiophene and 14-1. This material was taken up in 1:1 methanol:water (30 mL) and concentrated sulfuric acid (1 mL) was added. The mixture was heated to reflux for 2 hours, cooled to room temperature and concentrated. The residue was taken up in ethyl acetate, washed with saturated aqueous sodium bicarbonate, water and brine, dried over magnesium sulfate, filtered and concentrated.

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 75148-49-1.

Reference:
Patent; Aviara Pharmaceuticals, Inc.; Biediger, Ronald J.; Benish, Michele A.; Hardy, Lindsay Bonner; Boyd, Vincent A.; Market, Robert V.; Thrash, Thomas P.; Young, Brandon M.; (83 pag.)US2018/312523; (2018); A1;,
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