Month: June 2021

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. 116557-46-1, name is 3-Bromo-2-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 3-Bromo-2-methoxyaniline

Step 3[00174j IntlO (2.0 g, 9.9 mmol) was dissolved in dioxane (40 mL) and the vessel purged with nitrogen for 5 minutes. Next bis(pinacolato)diborone (3.77 g, 14.85 mmol), [1,1 ?-bis(diphenylphosphino)ferrocene] dichloropalladium (II) complex with dichloromethane (404 mg, 0.49 mmol) and potassium acetate (2.91 g, 29.7 mmol) were added. The flask was evacuated and backfilled with nitrogen, and then heated to 100 Cfor 15 hours. Water was added to quench the reaction and the product was then extracted with EtOAc. The combined organic layers were washed with brine (x3), dried over sodium sulfate, filtered, concentrated and purified using automated chromatography (elutes at 40% ethyl acetate) to provide Intl 1 (2.0 g, 8 1%). ?H NMR (400MHz, chloroform-d) oe 7.12 (dd,J=7.3, 1.8 Hz, 1H), 6.96-6.89 (m, 1H), 6.88-6.83 (m, 1H),3.82 (s, 3H), 1.37 (s, 12H). LC retention time 0.65 [J]. m/z: 250 (MHj.

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 116557-46-1.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; MOSLIN, Ryan M.; WEINSTEIN, David S.; WROBLESKI, Stephen T.; TOKARSKI, John S.; KUMAR, Amit; WO2014/74661; (2014); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

These common heterocyclic compound, 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, 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. HPLC of Formula: C11H25NO2

(b) tert-Butyl1-(trifluoroacetyl)azetidine-3-carboxylate 1,1-di-tert-butoxy-N,N-dimethylmethanamine (16.5 g, 81 mmol) was added to a solution of 1-(trifluoroacetyl)azetidine-3-carboxylic acid (5 g, 25 mmol) and the mixture was heated to reflux for 8 hours. LC-MS showed remaining starting material and therefore an additional amount of 1,1-di-tert-butoxy-N,N-dimethylmethanamine (21.2 g, 81 mmol) was added and the heating was continued over night. LC-MS showed still some remaining starting material (starting material/product about 1/2) and the THF was exchanged for toluene (100 mL) and the mixture heated to 100 C. (oil bath temperature) for 2 hours. The solvent was evaporated and the residue dissolved in EtOAc (200 mL). The organic phase was washed with NaHCO3(sat) (2*50 mL), water (2*50 mL), Brine (50 mL), dried (Na2SO4), filtered and evaporated to give the desired product. Yield: 4.5 g (70%).

The synthetic route of 1,1-Di-tert-butoxy-N,N-dimethylmethanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AstraZeneca AB; US2008/171732; (2008); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 109-85-3, name is 2-Methoxyethylamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 109-85-3

A solution of 6-amino-4-fluoronicotinonitrile (intermediate 21, 1.10 g, 8.02 mmol) in DMA (20 ml)was treated with 2-methoxyethylamine (2.07 ml, 24.1 mmol) and DIPEA (4.20 mL, 24.1 mmol),heated to 50 C and stirred for 15 h. The reaction mixture was cooled to room temperature and concentrated. The crude material was purified by normal phase chromatography (24 g silica gel cartridge, heptanes/EtOAc 100:0 to 0:100). The product containing fractions were concentrated and dried under vacuum to give the title compound as an off-white solid.

The synthetic route of 109-85-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; BUSCHMANN, Nicole; FAIRHURST, Robin Alec; FURET, Pascal; KNOePFEL, Thomas; LEBLANC, Catherine; MAH, Robert; NIMSGERN, Pierre; RIPOCHE, Sebastien; LIAO, Lv; XIONG, Jing; ZHAO, Xianglin; HAN, Bo; WANG, Can; WO2015/59668; (2015); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 36805-97-7, 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. 36805-97-7 name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, 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.

Example 10 2′-(6-Carbamimidoyl-1-methyl-1H-indol-3-ylmethyl)-4-methoxy-5′-methylcarbamoyl-biphenyl-2-carboxylic acid; Part A. 3-bromo-4-formyl-benzoic acid tert-butyl ester:; A solution of 3-bromo-4-methylbenzoic acid (5 g, 0.023 mol) in 40 mL toluene was heated to 80 C. in an oil bath and DMF-di-t-butylacetal (22.4 ml, 0.093 mol) was added dropwise over 20 min. The resulting mixture was heated for an additional 1 h and then cooled to rt and evaporated to dryness. Chromatography on silica gel (hexane/ethyl acetate 1:1) provided the t-butyl ester (5.1 g, 81%) which was dissolved in 50 mL CCl4 and treated with N-bromosuccinimide (6.7 g, 0.037 mol) and benzoylperoxide (0.22 g, 0.94 mmol). The mixture was then heated in an 80 C. oil bath overnight. Solvent was removed by evaporation, and residue was taken up in EtOAc and washed with water, sat’d Na2CO3 and brine then dried over anh. Na2SO4, filtered and concentrated. Chromatography on silica gel (hexane/ethyl acetate 1:1) provided the dibromide (7.5 g, 94%) to which was added 30 mL morpholine and the mixture was heated overnight at 60 C. After cooling to rt, the mixture was diluted with EtOAc and washed with 5% citric acid solution until aqueous phase stays at pH 4, then with sat’d bicarbonate solution and brine. Organic phase was dried and concentrated to provide the aldehyde in 74% yield after flash chromatography. 1NMR (500 MHz, CDCl3) delta 10.40 (s, 1H); 8.24 (s, 1H); 7.95 (m, 1H); 7.93 (m, 1H); 1.61 (s, 9H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, and friends who are interested can also refer to it.

Reference:
Patent; Smallheer, Joanne M.; Corte, James R.; US2005/228000; (2005); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 6851-80-5, The chemical industry reduces the impact on the environment during synthesis 6851-80-5, name is 1-(2-Methoxyphenyl)-N-methylmethanamine, I believe this compound will play a more active role in future production and life.

a N-(2-Methoxybenzyl)–N-(methyl)aminoacetonitrile A mixture of 2.0 g (13.2 mmole) of N-methyl-2methoxybenzylamine, 0.99 g (13.2 mmole) of chloroacetonitrile, and 2.80 g (26.5 mmole) of powdered sodium carbonate was stirred in 30 mL of acetone at room temperature for 4 days. The mixture was concentrated in vacuo and the residue purified by flash chromatography on 130 g of silica gel eluding with 83:17 hexanes: ethyl acetate to give 2.2g (87%) of an oil. 1 H NMR (CDCl3, 400 MHz, ppm): delta 2.43 (s, 3H), 3.48 (s, 2H), 3.62 (s, 2H), 3.83 (s, 3H), 6.88 (d, 1H), 6.93 (t, 1H), 7.2-7.3 (m, 2H).

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-(2-Methoxyphenyl)-N-methylmethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Merck & Co., Inc.; US5610165; (1997); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 349-65-5, The chemical industry reduces the impact on the environment during synthesis 349-65-5, name is 2-Methoxy-5-(trifluoromethyl)aniline, I believe this compound will play a more active role in future production and life.

5-(Trifluoromethyl)-2-methoxyaniline was treated with CDI, followed by 4-(1-oxoisoindolin-5-yloxy)aniline according to Method C2d to afford the urea. Entry 26: 4-Hydroxyacetophenone was reacted with 4-fluoronitrobenzene according to Method A13, Step 1 to give 4-(4-acetylphenoxy)nitrobenzene.

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-Methoxy-5-(trifluoromethyl)aniline, other downstream synthetic routes, hurry up and to see.

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; US2003/181442; (2003); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 6738-23-4, These common heterocyclic compound, 6738-23-4, name is 2,4-Dimethylanisole, 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.

Reference Example 32 2-Methoxy-3,5-dimethylbenzaldehyde To a solution of 1-methoxy-2,4-dimethylbenzene (8.00 g, 58.7 mmol) and 1,1-dichloromethyl methyl ether (7.40 g, 64.7 mmol) in methylene chloride (30 mL) was added titanium tetrachloride (20.0 g, 105 mmol) at 0 C. and the mixture was stirred at that temperature for 20 minutes. This reaction mixture was poured into iced water and the organic layer was taken, washed with saturated aqueous sodium hydrogen carbonate solution, dried over MgSO4, and filtered. The filtrate was concentrated under reduced pressure to provide 9.40 g of the title compound. Yield 98%. Oil. 1H-NMR (CDCl3) delta: 2.306 (3H, s), 2.312 (3H, s), 3.85 (3H, s), 7.25-7.27 (1H, m), 7.48 (1H, d, J=1.8 Hz), 10.3 (1H, s).

Statistics shows that 2,4-Dimethylanisole is playing an increasingly important role. we look forward to future research findings about 6738-23-4.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US6248766; (2001); B1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

17061-62-0, name is Bis(4-methoxybenzyl)amine, 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. Recommanded Product: 17061-62-0

To a stirred solution of 100.1 (100 g, 0.39 mol) in DCM (1 L) was added TEA (71 mL, 0.51 mol), followed by dropwise addition of methanesulfonyl chloride (36 mL, 0.47 mol). The internal temperature was kept between 5-10 C during the addition of methane sulfonyl chloride. Once the addition was complete, the cooling bath was removed and the mixture was stirred at RT until TLC analysis indicated that the reaction was complete. Thereafter, water (1 L) was added, the layers were separated and the aqueous layer was extracted with DCM (2 x 500 mL). The combined organic layers were washed with brine (2 x 1 L), dried over Na2SO4, and concentrated in vacuo. The residue was purified on a silica gel column, employing a gradient of 10-80% EtOAc in hexanes, to afford 120 g (0.36 mol, 92%) of 101.0 as white solid.1H-NMR (400 MHz, CDCl3) delta 7.26 (dd, J=2.12, 6.60 Hz, 4H) 6.91 (dd, J=2.12, 6.62 Hz, 4H) 4.28 (s, 4H) 3.83 (s, 6H) 2.75 (s, 3H).

The synthetic route of 17061-62-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; CHEN, Ning; CHEN, Yinhong; DEBENEDETTO, Mikkel V.; DRANSFIELD, Paul John; HARVEY, James S.; HEATH, Julie Anne; HOUZE, Jonathan; KHAKOO, Aarif Yusuf; LAI, Su-Jen; MA, Zhihua; NISHIMURA, Nobuko; PATTAROPONG, Vatee; SWAMINATH, Gayathri; YEH, Wen-Chen; KREIMAN, Charles; (308 pag.)WO2018/93579; (2018); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 17715-69-4, name is 1-Bromo-2,4-dimethoxybenzene, 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 17715-69-4, Product Details of 17715-69-4

General procedure: Synthesis of 4′-methoxybiphenyl-4-carbonitrile. A reaction vessel equipped with filtration frit was charged with polystyrene resin-bound benzyl(di-tert-butyl)phosphonium chloride (6.20 mg, 4% mol, 100-200 mesh resin containing 1.60 mmol/g phosphonium hydrochloride) and flushed with argon. Next, 5mL of degassed dioxane was added followed by 20 mL of diisopropylamine and reaction mixture was agitated for 1 h at room temperature. Subsequently, the solvent was removed and the resin washed with degassed dioxane (3×5 mL). The resin was resupended in dioxane (5.0 mL) and Pd2(dba)3·CHCl3 (5.20 mg, 2% mol) added and the reaction mixture was agitated for 12 h at room temperature. The Pd-doped resin becomes black in colour. The solvent was removed and catalyst washed with degassed dioxane (3×5 mL). 4-Bromobenzonitrile (45.5 mg, 0.25 mmol), 4-methoxyphenylboronic acid (42.0 mg, 0.28 mmol), Cs2CO3 (179.2 mg, 0.55 mmol), 5 mL of degassed dioxane were added and the suspension agitated for 72h at room temperature. The solution was filtered and the Pd-doped catalyst re-suspended and washed with degassed dioxane (3 x 5 mL). Evaporation of the combined dioxane extracts under vacuum and purification by chromatography on silica gel (ethyl acetate/hexane 1:9) afforded the title compound (41 mg, 80%). All entries reported in table 2 were conducted under the above conditions.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Ullah, Ehsan; McNulty, James; Sliwinski, Marcin; Robertson, Al; Tetrahedron Letters; vol. 53; 31; (2012); p. 3990 – 3993;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 589-10-6, name is (2-Bromoethoxy)benzene, This compound has unique chemical properties. The synthetic route is as follows., Safety of (2-Bromoethoxy)benzene

General procedure: Anhydrous K2CO3 (1.2 M equiv) was added to the solution of GA or compound 42 (0.2 mmol) and halogenating agents (1.2 M equiv) in dry DMF (5 mL). The reaction mixture was stirred at room temperature until the starting material was not observed by TLC. The mixture was treated with H2O (20 mL), the aqueous layer was extracted with EtOAc (2×20mL). The joined organic extracts were washed three times with H2O (60 mL) and saturated NaCl (60 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated to dryness under reduced pressure. The residue was chromatographed using a silica gel column to afford the pure target products.

According to the analysis of related databases, 589-10-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wang, Li-Jun; Geng, Chang-An; Ma, Yun-Bao; Huang, Xiao-Yan; Luo, Jie; Chen, Hao; Zhang, Xue-Mei; Chen, Ji-Jun; Bioorganic and Medicinal Chemistry Letters; vol. 22; 10; (2012); p. 3473 – 3479;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem