Category: ethers-buliding-blocks

These common heterocyclic compound, 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine, 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. 20781-20-8

Intermediate 3C:; [00197] To Intermediate 3B (3.0 g, 11.99 mmol) in toluene (18 mL) was added (2,4-dimethoxyphenyl)methanamine (2.476 mL, 16.48 mmol). The mixture was stirred at 125 0C (oil bath) for 3.5 h. The color changed from deep red to yellow. After the mixture cooled to rt, it was triturated with EtOAc/hexanes (1 : 2) and left standing overnight. The yellow precipitate was collected by filtration to give Intermediate 3C (3.92 g, 96% yield).

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 20781-20-8.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2008/79836; (2008); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 39021-83-5, name is 1,4-Dimethoxy-2,3-dimethylbenzene, 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 39021-83-5, name: 1,4-Dimethoxy-2,3-dimethylbenzene

2.1.b 1-(chloromethyl)-2,5-dimethoxy-3,4-dimethylbenzene In a round bottom flask, methoxy- protected hydroquinone (1.10 g, 6.62 mmol) was dissolved in conc. HCl and stirred at rt. ZnCl2 (0.90 g, 6.62 mmol) and paraformaldehyde (0.27 g, 7.9 mmol) were then added and stirred at rt. After 2 h, water was added to the flask and the organics were extracted with ether (3*30 mL), dried over Na2SO4, and concentrated down to a green-brown solid. Flash column chromatography on silica gel in a solution of 2% ether:hexanes afforded an off-white solid that contained a 4:1 mixture of the inseparable mono- and dichloromethylquinone (1.12 g, 91%). This mixture was taken on to the next step without further purification.

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:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; US2007/203080; (2007); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 59557-91-4, These common heterocyclic compound, 59557-91-4, name is 4-Bromo-2-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.

(0677) 4-Bromo-2-methoxyaniline (6.8 g, 33.7 mmol) and di-tert-butyl dicarbonate (8.9 g, 40.8 mmol) were dissolved in tetrahydrofuran (100 mL). Under the protection of nitrogen gas, the reaction was carried out under reflux for 22 h, and the mixture was cooled. The solvent was removed by distillation under reduced pressure, and ethyl acetate (150 mL) was added. The mixture was washed with 1 mol/L hydrochloric acid, and the water phase and the organic phase were separated. The organic phase was dried with anhydrous sodium sulfate, and filtrated under suction. The filtrate was concentrated to get the title compound (8.3 g, yield: 81.6%).

The synthetic route of 59557-91-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Xuanzhu Pharma Co., Ltd.; WU, Frank; (117 pag.)US2017/112833; (2017); 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. 6298-96-0, name is 1-(4-Methoxyphenyl)ethylamine, A new synthetic method of this compound is introduced below., category: ethers-buliding-blocks

Synthesis of (S)-(-)-1-(4-hydroxyphenyl)ethylamine hydrobromide (6) A solution of (S)-(-)-1-(4-methoxyphenyl)ethylamine (5, 75 g, 496.7 mmol) in 30% hydrogen bromide in acetic acid (350 mL, Aldrich) in a 1 liter sealed tube was heated at 100-110 C. in an oil bath for 6 hours. The reaction was cooled to room temperature, and nitrogen gas was bubbled into the solution to purge the excess HBr (the HBr was purged into aqueous NaOH). Volatiles were then removed in vacuo to afford the crude phenol amine HBr salt 9 (110 g) as a brown oil, which was used in the next reaction without further purification.

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; Bristol-Myers Squibb Company; US2008/9534; (2008); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 6358-77-6, A common heterocyclic compound, 6358-77-6, name is 5-Bromo-2-methoxyaniline, molecular formula is C7H8BrNO, 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.

b. 4-(5-Bromo-2-methoxyanilino)-2-(3-pyridinyl)-6-(trifluoromethyl)pyrimidine The title compound was prepared from a mixture of 4-chloro-2-(3-pyridinyl)-6-(trifluoromethyl)pyrimidine (50 mg, 0.193 mmol) and 5-bromo-2-methoxyaniline (39 mg, 0.193 mmol) similar to Example 117 and isolated as a tan solid (26 mg, 32%). 1H NMR (CDCl3): 9.67-9.66 (m, 1H), 8.77-8.71 (m, 3H), 7.55 (s, 1H), 7.48-7.43 (m, 1H), 7.24 (dd, J=2.4, 8.7 Hz, 1H), 6.92 (s, 1H), 6.83 (d, J=9.0 Hz, 1H), 3.93 (s, 3H).

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; Cytovia, Inc.; US2003/69239; (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. 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine, A new synthetic method of this compound is introduced below., Formula: C9H13NO2

Weighing 167 mg of 2,4-dimethoxybenzylamine, 6.1 mg of Ru catalyst,3.0 mL of ethanol was weighed, 290 mg of 5-HMF was weighed,In 10mL autoclave mixed evenly, the system with 10bar hydrogen replacement 3 times,The reaction initial hydrogen pressure was 20 bar, the temperature was 110 C,The reaction time was 12 h. After the end of the reaction, the ethanol was removed under reduced pressure,The residue was separated using a silica gel columnWith a color solid of 325.4 mg, yield 84%.

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; Dalian Institute of Chemical Physics; Zhang Zongchao; Xu Zhanwei; Wan Lu; Yan Peifang; (17 pag.)CN106632165; (2017); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 29578-83-4, 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. 29578-83-4 name is 1-Bromo-3-methoxy-5-methylbenzene, 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.

A mixture of D-6-1 (100 g, 497 mmol), NBS (88.5 g, 497 mmol), and AIBN (10 g, 50 mmol) in CCl4 (700 mL) is heated to reflux for 12 h. The mixture is cooled to ambient temperature, diluted with H2O, and extracted with EtOAc. The organic layer is separated, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue is purified by flash silica gel chromatography to afford D-6-2 (48 g, 42% yield).

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

Reference:
Patent; Boehringer Ingelheim International GmbH; BRENNEMAN, Jehrod Burnett; GINN, John David; HOPKINS, Tamara Denise; LOWE, MIchael D.; SARKO, Christopher Ronald; WESTBROOK, John A.; YU, Maolin; ZHANG, Zhonghua; (233 pag.)US2016/24059; (2016); A1;,
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. 27060-75-9, name is 1-Bromo-4-methoxy-2-methylbenzene, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 27060-75-9

General procedure: An argon flushed pressure tube was charged with indole (59 mg, 0.5mmol), bromobenzene (62 muL, 0.5 mmol), Mo(CO)6 (132 mg, 0.5mmol), DBU (75 muL, 0.5 mmol), K3PO4 (106 mg, 0.5 mmol), Pd(OAc)2(3.4 mg, 3 mol%), BuPAd2 (10.8 mg, 6 mol%), and DMF (3 mL). The tubewas subsequently sealed and the mixture was stirred at 120 C for 16h. Afterwards, the reaction mixture was diluted with CH2Cl2 (3 × 5mL) and washed with H2O (3 × 5 mL). The aqueous layer was extractedwith CH2Cl2 (2 × 5 mL), the combined organic phases were dried(Na2SO4), and the solvent was evaporated. The crude product was purifiedby column chromatography (pentane-EtOAc (8:2) with additionof 0.5% Et3N) to give benzoylindole as a viscous oil that solidifiedon standing; yield: 98 mg (89%); mp 64-65 C.

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 27060-75-9.

Reference:
Article; Wu, Xiao-Feng; Oschatz, Stefan; Sharif, Muhammad; Langer, Peter; Synthesis; vol. 47; 17; (2015); p. 2641 – 2646;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 61367-43-9, A common heterocyclic compound, 61367-43-9, name is cis-4-Methoxycyclohexanamine hydrochloride, molecular formula is C7H16ClNO, 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 227 6-(4-(4-cyanophenyl)-5-hydroxy-lH-pyrazol-l-yl)-N-((ls,4s)-4- methoxycyclohexyl)nicotinamide [0985] Combined 6-(4-(4-cyanophenyl)-5 -hydroxy- lH-pyrazol-l-yl)nicotinic acid (100 mg, 0.327 mmol), (ls,4s)-4-methoxycyclohexanamine, HC1 (81 mg, 0.490 mmol), and Nl- ((ethylimino)methylene)-N3,N3-dimethylpropane-l,3-diamine, HC1 (94 mg, 0.490 mmol) in DMF (1.555 mL). Then added lH-benzo[d][l,2,3]triazol-l-oL, water (75 mg, 0.490 mmol) and Hunig’s base (0.171 mL, 0.980 mmol) and stirred for 4 hours at room temperature. The reaction mixture was acidified to a pH of 5 to give a solid. The solid was washed with 50 mL MeOH and 50 mL hexanes, and then dried to afford the title compound (95.3 mg, 66.4%) as light yellow solid. NMR (400 MHz, DMSO-d6) delta ppm 1.24 (br. s., 2 H) 1.39 (d, J=14.7 Hz, 2 H) 1.89 (br. s., 2 H) 2.05 (d, J=10.9 Hz, 2 H) 3.25 (s, 3 H) 3.35 (br.s., 2 H) 7.80 (d, J=8.3 Hz, 2 H) 8.82 – 8.96 (m, 1 H). MS m/z [M+H]+ 418.4.

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; TAKEDA PHARMACEUTICAL COMPANY LIMITED; BROWN, Jason, W.; DAVIS, Melinda; IVETAC, Anthony; JONES, Benjamin; KIRYANOV, Andre, A.; KUEHLER, Jon; LANIER, Marion; MIURA, Joanne; MURPHY, Sean; WANG, Xiaolun; WO2014/160810; (2014); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 458-50-4,Some common heterocyclic compound, 458-50-4, name is 4-Bromo-3-fluoroanisole, molecular formula is C7H6BrFO, 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.

A degassed solution of 3-amino-furo[3,2-c]pyridine-2-carboxylic acid ethyl ester (206 g, 1.0 mmol), l-bromo-2-fluoro-4-methoxy-benzene (246 mg, 1.2 mmol), Pd2dba3 (46 mg, 0.050 mmol), Xantphos (58 mg, 0.10 mmol) and K3PO4 (254 mg, 1.2 mmol) in toluene (5 ml) was heated to 1100C then stirred for 18 hours. The reaction mixture was cooled to ambient temperature then diluted with EtOAc and filtered through a pad of celite. The filtrate was concentrated in vacuo to give a black oil. The oil was purified by flash chromatography (Si-SPE, MeOH: DCM, gradient 0: 100 to 10:90) to provide the title compound as a yellow oil (130 mg, 39percent). LCMS (method B): Rx = 2.93 min, M+H+ = 331.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-3-fluoroanisole, its application will become more common.

Reference:
Patent; GENENTECH, INC.; WO2008/24725; (2008); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem