Ethers-buliding-blocks

Synthetic Route of 454-90-0, A common heterocyclic compound, 454-90-0, name is 3-(Trifluoromethyl)anisole, molecular formula is C8H7F3O, 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 stirred solution of 1-methoxy-3-(trifluoromethyl)benzene (9.8 mL, 68 mmol) in 50 mL THF under N2 at O0C was added n-BuLi (1.6 M in hexanes, 45 mL, 68 mmol) dropwise. The reaction mixture was stirred at O0C for 2 h, then triisopropylborate (11.6 ml_, 68 mmol) was added. The reaction mixture was slowly warmed up to room temperature and stirred overnight. A solution of 10% HCI in water was added and the mixture was stirred for 1 h. The mixture was extracted with CH2CI2 (3X), The organic layers were combined, washed with brine and dried over Na2SO4 to give 8.14 g of 2-methoxy-4-(trifluoromethyl)phenylboronic acid as a viscous oil. The crude was directly used in the next step without further purification.

The synthetic route of 454-90-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2008/12623; (2008); A1;,
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Application of 5467-58-3, 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 5467-58-3 as follows.

To a solution of 1-bromo-4-methoxynaphthalene (4.72 g, 20 mmoL) in 1, 4-dioxane /H2O (80 mL/20mL) was added 4, 4, 5, 5-tetramethyl-2- (1, 4-dioxaspiro [4.5] dec-7-en-8-yl) -1, 3, 2-dioxaborolane (5.32 g, 10 mmol), Pd (dppf) Cl2 (1462 mg, 2.0 mmol) and Cs2CO3 (9.75 g, 30 mmol) and the mixture was heated at 70 for 5 hours. Then evaporated the solvent under reduced pressure and the residue was purified by column chromatography (PE: EA=5: 1) to give product as an oil (4.1 g in 69% yield). [M+H] +=297.

According to the analysis of related databases, 5467-58-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BEIGENE, LTD.; WANG, Hexiang; GUO, Yunhang; REN, Bo; WANG, Zhiwei; ZHANG, Guoliang; ZHOU, Changyou; (353 pag.)WO2018/54365; (2018); A1;,
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Synthetic Route of 402-52-8,Some common heterocyclic compound, 402-52-8, name is 1-Methoxy-4-(trifluoromethyl)benzene, molecular formula is C8H7F3O, 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-methoxy-5-(trifluoromethyl)benzoic acid (12-3). nBuLi (276 mL, 2.5 M, 0.69 mol, 1.1 equiv) and KOtBu (77 g, 0.69 mol, 1.1 equiv) were added to a THF solution (1 L) of crude 12-2 (110 g) at -78 0C. The reaction was stirred at -78 0C for 4 h. Dry CO2 was bubbled into the solution at -78 0C for 1 h. The reaction was allowed to warm to 25 0C over 0.5 h. NaOH (6N, 300 mL) and H2O were added to the resulting reaction mixture. The mixture was extracted with t-butylmethyl ether (400 mL x 2). The aqueous layer was acidified with HCl (6N) to pH 1 and extracted with EtOAc (300 mL x 4). The combined EtOAc extracts were concentrated and re- dissolved in CH2Cl2. The solution was dried (Na2SO4), filtered through a pad of Celite and concentrated. Flash chromatography on silica gel (1:1 PE/EtOAc) yielded 82 g of compound 12-3 (53% for 2 steps): 1H NMR (400 MHz, CDCl3) delta 8.45 (s, 1 H), 7.81 (d, J= 8.0 Hz5 1 H), 7.16 (d, J= 8.0 Hz5 1 H), 4.13 (s, 3 H); MS (ESI) m/z 221.0 (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 1-Methoxy-4-(trifluoromethyl)benzene, its application will become more common.

Reference:
Patent; TETRAPHASE PHARMACEUTICALS, INC.; DENG, Yonghong; PLAMONDON, Louis; SUN, Cuixiang; XIAO, Xiao-Yi; ZHOU, Jingye; SUTCLIFFE, Joyce, A.; RONN, Magnus, P.; WO2011/25982; (2011); A2;,
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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. 103291-07-2, name is 4-Bromo-1-fluoro-2-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 103291-07-2

In a 1 I three necked round bottom flask, flame dried, under argon, 2-fluoro-5-bromoanisole (27.40 g; 133.64 mmol; 1.20 eq.) was diluted in THF (200 mL) and the mixture was cooled to -78C. Then, n-Butyllithium 1.6M in hexane (98.0 mL; 1.6 mol/L; 156.8 mmol; 1.41 eq.) was slowly added during 20 min, keeping temperature below -65C and the reaction was stirred at -78C for 1h. Next, a solution of 4-chloro-N-methoxy-N-methyl-pentanamide (20.00 g; 111.33 mmol; 1.00 eq.) in THF (100 mL) was slowly added to the lithiated species during 25 min, keeping temperature below -65C. The reaction was then stirred 40 min at -78C and quenched by addition of aqueous 1N HCI (500 mL). The mixture was allowed to warm to rt and was extracted EtOAc (3 x 250 mL). Combined organic layer was dried over MgS04, filtered, and concentrated to dryness to give 4-chloro-1-(4-fluoro-3-methoxy-phenyl)pentan-1-one (32.50 g; quantitative ; 47% LC/MS purity) as a yellow liquid, used in the next step without further purification.

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 103291-07-2.

Reference:
Patent; Eng Bang Tiba; Ba Seu-ma-tin; Kon Tal-sil-bi-e; Ju Ni-en-jang—ru-i-seu; Ma Sa-reu-di-e-reu-keu-ri-seu-tin; Mon Tal-be-ti-keu-ri-seu-chan; Su Deu-an-ne; (111 pag.)KR2019/137803; (2019); A;,
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Electric Literature of 111-95-5, A common heterocyclic compound, 111-95-5, name is Bis(2-methoxyethyl)amine, molecular formula is C6H15NO2, 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.

Compound 6-3 (5.3 g, 17.4 mmol) was dissolved in 1,4-dioxane (60 mL), followed by addition of compound 5-1 (4.85 g, 36.5 mmol), and potassium carbonate (4.9 g, 34.8 mmol) was added under stirring in batches, followed by stirring the reaction overnight at 70 C., TLC monitoring showed that the starting material 6-3 was completely reacted. The solvent was removed under reduced pressure to obtain a concentrated residue. The concentrated residue was dispensed with dichloromethane (20 mL), an appropriate amount of silica gel was added and the sample was stirred, spin-dried under reduced pressure and directly placed on a silica gel column for column chromatographic purification, with an eluent (dichloromethane:methanol=20/1-5/1) to obtain the target product 10-1 (2.2 g, 47.7%) as a pale yellow oil, LC-MS: m/z=266[M+H]+.

The synthetic route of 111-95-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shenzhen China Resources Gosun Pharmaceutical Co., Ltd.; Jiang, Xiongjie; Huang, Quanhua; Yang, Zhanao; (43 pag.)US2017/2028; (2017); A1;,
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Reference of 74654-07-2, The chemical industry reduces the impact on the environment during synthesis 74654-07-2, name is 2-(2-(2-Methoxyethoxy)ethoxy)ethanamine, I believe this compound will play a more active role in future production and life.

HATU (500 mg, 1.315 mmol) was added to a stirred solution of 3-((4-((tert-butoxycarbonyl)amino)naphthalen-1-yl)oxy)pyridin-2-yl)amino)-5-ethynylbenzoic acid (see Example 52(iii) above; 500 mg, 1.009 mmol), 2-(2-(2-methoxyethoxy)ethoxy)-ethanamine (277 mg, 1.695 mmol) and triethylamine (250 muL, 1.796 mmol) in N,N-dimethylformamide (10 mL). The mixture was stirred at rt for 18 h. The mixture was diluted with EtOAc (50 mL) and washed with water (50 mL), 20% brine (3*50 mL) and saturated brine (50 mL). The organic phase was dried (MgSO4), filtered and concentrated under reduced pressure. The crude product was purified by chromatography on the Companion (40 g column, EtOAc) to afford the sub-title compound (580 mg) as a tan foam. LCMS m/z 641 (M+H)+ (ES+); 639 (M-H)- (ES-)

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, 2-(2-(2-Methoxyethoxy)ethoxy)ethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Topivert Pharma Limited; Respivert Limited; BAKER, Thomas Matthew; FYFE, Matthew Colin Thor; HARBOTTLE, Gareth William; HASIMBEGOVIC, Vedran; MEGHANI, Premji; RIGBY, Aaron; SAMBROOK-SMITH, Colin; THOM, Stephen Malcolm; US2014/296208; (2014); A1;,
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Reference of 886762-08-9, The chemical industry reduces the impact on the environment during synthesis 886762-08-9, name is 5-Bromo-2-(trifluoromethoxy)aniline, I believe this compound will play a more active role in future production and life.

General Procedure: Methyl 2-{[4-(chlorosulfonyl)-2,3-dimethylphenyl]oxy}propanoate (7) (4 g, 13.0 mmol) was dissolved in pyridine (10 mL). After 5 min, 3-bromo-2-chloroaniline (3.22 g, 15.6 mmol) was added. The reaction was complete within a few hours. The reaction mixture was then extracted using diethyl ether. The combined organic phases were washed with 1N HCl and brine, dried over sodium sulfate, filtered, and concentrated in vacuo to afford the title compound which was used without further purification.

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, 5-Bromo-2-(trifluoromethoxy)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Evans, Karen A.; Shearer, Barry G.; Wisnoski, David D.; Shi, Dongchuan; Sparks, Steven M.; Sternbach, Daniel D.; Winegar, Deborah A.; Billin, Andrew N.; Britt, Christy; Way, James M.; Epperly, Andrea H.; Leesnitzer, Lisa M.; Merrihew, Raymond V.; Xu, Robert X.; Lambert, Millard H.; Jin, Jian; Bioorganic and Medicinal Chemistry Letters; vol. 21; 8; (2011); p. 2345 – 2350;,
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Some common heterocyclic compound, 17061-62-0, name is Bis(4-methoxybenzyl)amine, molecular formula is C16H19NO2, 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. COA of Formula: C16H19NO2

To a cooled (-35 C) solution of 4-Fluoro-3-nitrobenzenesulfonyl chloride (4.89 g, 20.42 mmol) in THF (50 mL) was added Triethylamine (3.13 mL, 22.46 mmol), followed by addition of Bis-(4-methoxybenzyl)amine (4.97 mL, 20.7 mmol) in THF (50 mL) solution over 30 min. while the temperature was kept at -35 C. After completion of the addition, the temperature was allowed slowly to warm to 0 C over 1 h., and the mixture was stirred at 0 C for an additional hour. The mixture was neutralized with 1 N HC1 to pH about 4-5 and diluted with EtOAc (100 mL). The organic layer was separated, washed with 1 N HC1 (10 mL), 7.5% NaHC03 aqueous solution (20 mL), and brine, dried over Na2S04, filtered, and concentrated under reduced pressure. The residue was treated with DCM (30 mL), and hexane was added to the suspension until it became cloudy. The resulting suspension was sonicated for 2 min. and left at r.t. for 1 h. The mixture was filtered and washed with hexane to afford the desired title product (6.85 g) without further purification. The mother liquid was concentrated under reduced pressure. The residue was treated with DCM (5 mL) and hexane was added as the procedures mentioned above to afford the additional 0.51 g of the title product. Total product 4-fluoro-N,N-bis[(4-methoxyphenyl)methyl]-3-nitro-benzenesulfonamide obtained is 7.36 g (78%). NMR (400 MHz, DMSO-de): d 8.18-8.23 (m, 2 H), 7.75-7.79 (q, 1 H), 7.08 (d, 4 H), 6.81 (d, 4 H), 4.31 (s, 4 H), 3.71 (s, 6 H). 19F NMR (376 MHz, DMSO-d6): d -112.54 (s, 1 F). LCMS calculated for C22H22FN2O6S (M+H)+: m/z = 461.11; found: 461.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 17061-62-0, its application will become more common.

Reference:
Patent; PRELUDE THERAPEUTICS, INCORPORATED; ZHUO, Jincong; LEAL, Raul; SHETTY, Rupa; LUENGO, Juan; COMBS, Andrew, Paul; (525 pag.)WO2020/97577; (2020); A1;,
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Reference of 115144-40-6, 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 115144-40-6 as follows.

1, 2-Difluoro-4-methoxy-benzene (100mg, 0. 69MMOL) and sodium methan- ethiolate (148mg, 2. 08MMOL) were dissolved in N, N-dimethylformamide (2mL) and the reaction mixture stirred at 60C for 18 hours. Additional sodium METHANETHIOLATE (99mg, 139MMOL) was added and the reaction mixture was heated to 100C for 18 hours. The reaction mixture was diluted with water and extracted with ether (x 2). The ether extracts were washed with water (x 2), dried (MGS04) and then concentrated under reduced pressure. The residue was taken up in a pentane: ether 1: 1 solution (2mL) and filtered through a plug of silica in a pipette, and then washed through with a pentane: ether 1: 1 solution (5mL). The solution was concentrated under reduced pressure to yield the title product as a colourless oil, 135mg. H NMR (CDCI3, 300MHZ) 8 : 2.45 (s, 3H), 3.80 (s, 3H), 6.65 (dd, 1H), 6.80 (DD, 1 H), 6.95 (dd, 1 H).

According to the analysis of related databases, 115144-40-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER LIMITED; PFIZER INC.; WO2005/9964; (2005); 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 645-36-3 as follows. Recommanded Product: 2,2-Diethoxyethanamine

[00231] To a solution of cyanogen bromide (25 g, 236.03 mmol) in hexane (80 mL) was added a solution of the amino-acetaldehyde diethyl acetal (34.3 mL, 236.03 mmol) in diethyl ether (80 mL) at room temperature. The resulting mixture was stuffed overnight. A white solid was formed and was removed by filtration and washed with diethyl ether. The filtrate was concentrated and purified by flash chromatography on silica gel (eluted with 0/100 to 5/95 methanol/dichloromethane) to afford N- (2,2-diethyloxyethyl)carbodiimide (27 g, 72% yield) as a bright yellow oil. Rt (retention time) = 1.82 mm; MS m/z: 159.20 [M+1].

According to the analysis of related databases, 645-36-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; CHOI, Hwan, Geun; LIANG, Yanke; GRAY, Nathanael; (135 pag.)WO2016/14542; (2016); A1;,
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