Month: September 2021

Application of 5905-69-1, 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. 5905-69-1, name is 1-Bromo-4-(difluoromethoxy)benzene, This compound has unique chemical properties. The synthetic route is as follows.

Example 346: Ethyl (2E)-3-{1-[4-(difluoromethoxy)phenyl]-3-(2-phenylethyl)-1H-indol-5-yl}propenoate; To a solution of the compound obtained at Example 141 (200 mg) in n-butyl acetate (15 ml) were added 1-bromo-4-(difluoromethoxy)benzene (281 mg), palladium acetate (28 mg), 2-(di-tert-butylphosphino)biphenyl (75 mg) and tripotassium phosphate (535 mg), and the mixture was heated and stirred at 120C for 12 hours. The reaction mixture was cooled to room temperature, then the insolubles were filtered off, the filtrate was distilled off in vacuo and the residue obtained was purified by silica gel column chromatography (hexane:ethyl acetate=19:1 to 9:11) to afford the above-identified compound (227 mg).

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-4-(difluoromethoxy)benzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Asubio Pharma Co., Ltd.; EP2141148; (2010); A1;,
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Application of 458-52-6, 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. 458-52-6, name is 2-Fluoro-4-methoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 13 Benzamide, 2-amino-4,6-dimethoxy-N-(2-fluoro-4-methoxyphenyl) To a mixture of 200 mg (1.42 mmol)of 4-amino-3-fluoroanisole and 1M sodium bis(trimethylsilyl)amide (4.39 mmol) in THF solution at room temperature under nitrogen atmosphere, 320 mg (1.42 mmol) of the isatoic anhydride prepared in Example 5, was added followed by the addition of 2 mL of N,N-dimethylacetamide. The suspension was heated at 90° C. for 4 hours. After completion of the reaction, as monitored by HPLC, the mixture was cooled to room temperature, diluted with EtOAc and 1N HCl, and the resulting layers were separated. The aqueous layer was extracted with EtOAc twice, and the combined organic extracts were washed with water, saturated NaHCO3, brine, dried over Na2SO4 and concentrated. The residue was dissolved in CH2Cl2 and chromatographed on silica using 30percent EtOAc in hexane as eluent. A total of 220 mg (48percent) of a yellow solid was obtained. C16H17FN2O4=320 g/mol; ESI-LC/MS (M+H)+=321.1; 1H NMR (400 MHz, CDCl3): delta10.0 (1H, s), 8.26 (1H, t, J=8.8 Hz), 6.70 (2H, m), 6.42 (2H, broad), 5.85 (1H, d, J=2.6 Hz), 5.82 (1H, d, J=2.6 Hz), 3.94 (3H, s), 3.79 (6H, s).

The synthetic route of 2-Fluoro-4-methoxyaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Gungor, Timur; Corte, James R.; US2003/220227; (2003); A1;,
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Synthetic Route of 873980-68-8, These common heterocyclic compound, 873980-68-8, name is 4-Bromo-2-methoxy-5-methylaniline, 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 2: BBr3 (1 M solution in CH2CI2, 138 mL, 138 mmol) was added to a solution of the intermediate of step 1(12.0 g, 55.6 mmol) in CH2CI2 at OC and the mixture was stirred rt for 10 h. Aq. NaHCO3 was added and the mixture was extracted with CH2CI2. The combined organic layers were washed with water, brine, were dried the volatiles were removed under reduced pressure. The residue was purified by chromatography (SiC2, Cy/EtOAc) to yield the desired compound (10 g, 89%).

The synthetic route of 873980-68-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GRUeNENTHAL GMBH; NORDHOFF, Sonja; VOSS, Felix; WACHTEN, Sebastian; KLESS, Achim; RITTER, Stefanie; WO2015/90580; (2015); A1;,
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Some common heterocyclic compound, 1836-62-0, name is 2-(2-Methoxyphenoxy)ethylamine, molecular formula is C9H13NO2, 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: 2-(2-Methoxyphenoxy)ethylamine

In a dry reaction flask, 4-(2,3-epoxy propoxy) carbazole (50 gm.0.21 moles), 2-(2-methoxy phenoxy) ethyl amine (75.5 gm. 0.45 moles) and 500 ml of ethyl acetate were charged and heated to reflux for about 24 hours. After completion of the reaction, solvent was distilled off from the reaction mixture to obtain 125 gm of the residue. Ethyl acetate (312 ml) and water (312 ml) were added to the residue and stirred for about 15 minutes. Reaction mixture pH was adjusted to about 3 with 40 ml (0.68 moles) of phosphoric acid at room temperature. Reaction mixture was stirred for about 11 hours and filtered the solid to obtain carvedilol phosphate. The wet solid thus obtained was slurred in 325 ml of acetone at 26 0C for about 30 minutes. The solid was filtered and dried to obtain the title compound. Yield: 50 gm

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1836-62-0, its application will become more common.

Reference:
Patent; SHODHANA LABORATORIES LIMITED; WO2009/122425; (2009); 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 38336-04-8 as follows. COA of Formula: C9H13NO

General procedure: Ethyl 2-(4-chloro-3-nitrophenyl)-2-methylpropanoate (3a)(16.15 g, 0.0594 mol), 4 (27.77 g, 0.149 mol), K2CO3 (28.69 g,0.208 mol), KI (0.99 g, 5.94 mmol), TBAB (1.91 g, 5.94 mmol) and150 mL DMSO were added into a round-bottomed flask. The mixturewas heated to 120 C for 24 h then cooling to room temperature.The reaction mixture was diluted with saturated NH4Claqueous solution (250 mL) and extracted with CH2Cl2 (450 mL).The combined organic layer was washed with brine (300 mL), driedover anhydrous sodium sulfate, filtered, and concentrated in vacuo.The residue was purified by silica gel column chromatography (PE:EtOAc = 4:1) to give compound 5a (15.82 g) as yellow oil in 69%yields.

According to the analysis of related databases, 38336-04-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Chen, Dongxing; Shi, Jinyu; Liu, Jing; Zhang, Xueying; Deng, Xiaoying; Yang, Yanyan; Cui, Shuang; Zhu, Qihua; Gong, Guoqing; Xu, Yungen; Bioorganic and Medicinal Chemistry; vol. 25; 2; (2017); p. 458 – 470;,
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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. 321-28-8, name is 1-Fluoro-2-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C7H7FO

A solution of 2-fluoro-anisole (6.0 g, 47 mmol) and N, N, Nu’, ‘- tetramethylethylenediamine in THF (250 mL) was cooled to – 78 C and treated dropwise with sec -butyl lithium (1.3 M in cyclohexane, 38 mL, 49 mmol). The mixture was stirred for 2 h at – 78 C and then treated with dimethylformamide (3.6 mL, 47 mmol). Stirring continued for an additional 10 min and then acetic acid (20 mL) followed by water (150 mL) was added to the mixture. The mixture was warmed to ambient temperature and then diluted with ethyl acetate. The organic layer was washed with 1 M HCI, and brine. The organic layer was dried over Na2S04 and concentrated under reduced pressure to give crude 2-flouro-3-methoxybenzaldehyde (4.7 g, yield 64%) as a yellow solid. NMR (400 MHz, CDC13) (ppm) 10.40 (s, 1H), 7.45-7.40 (m, 1H), 7.23-7.18 (m, 2H), 3.94 (s, 3H).

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 321-28-8.

Reference:
Patent; ANACOR PHARMACEUTICALS, INC.; AKAMA, Tsutomu; JARNAGIN, Kurt; ZHANG, Yong-kang; ZHOU, Yasheen; PLATTNER, Jacob, J.; SULLIVAN, David, C.; WO2015/13318; (2015); A1;,
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Synthetic Route of 32338-02-6, The chemical industry reduces the impact on the environment during synthesis 32338-02-6, name is 2-Bromo-4-methoxyaniline, I believe this compound will play a more active role in future production and life.

General procedure: A mixture of benzyl 1-oxa-6-azaspiro[2.5]octane-6-carboxylate (247 mg, 1.0 mmol), 2-bromo-4-methoxyaniline (303 mg, 1.5 mmol) and lithium perchlorate (190 mg, 1.7 mmol) were taken in acetonitrile (3.0 mL). The reaction mixture was heated to 90 °C for 18 h. The reaction mixture was diluted with ethyl acetate (20 mL) and washed with water. The organic layer was dried over sodium sulfate and concentrated under reduced pressure, and the product was purified by column chromatography (silica gel, 50percent EtOAc/hexanes) to provide benzyl 4-(((2-bromo-4-methoxyphenyl)amino)methyl)-4-hydroxypiperidine-1-carboxylate, 5c (358 mg, 80percent) as a colourless syrup.

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-Bromo-4-methoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kurissery, A. Tony; Rajkumar, G. Abraham; Arvapalli, Venkata Satyanarayana; Pitchumani, Venkatachalam; Tetrahedron Letters; vol. 58; 37; (2017); p. 3607 – 3611;,
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Electric Literature of 27060-75-9, 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.

To a CCl4 solution (125 mL) of 2-bromo-5-methoxytoluene (0.050 mol) and NBS (0.055 mol) was added AIBN (0.001 mol), and the mixture was stirred at 80 C for 18 h. The mixture was diluted with hexane before filtration through a Celite pad. Evaporation of the solvent followed by washing of the residue with ethyl acetate gave 4-bromo-3-(bromomethyl)anisole.

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-4-methoxy-2-methylbenzene. I believe this compound will play a more active role in future production and life.

Reference:
Article; Yoshida, Hiroto; Yoshida, Ryuma; Mukae, Masashi; Ohshita, Joji; Takaki, Ken; Chemistry Letters; vol. 40; 11; (2011); p. 1272 – 1274;,
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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 54314-84-0 as follows. Computed Properties of C10H13BrO

To a solution of – uoro- , – y roxy- enza e y e (11.15 g, 71.42 mmol) in anhydrous DMSO (88 mL) under nitrogen were added sequentially sodium t-butoxide (13.72 g, 142.84 mmol) and benzyl-3-bromopropyl ether (17.29 g, 78.56 mmol) and the reaction mixture stirred at rt for 18 h. The mixture was diluted with water (400 mL) and extracted with EtOAc (4×100 mL). The combined organic layer was washed with water and brine, dried over MgS04, filtered and concentrated in vacuo. Purification was completed by flash chromatography (20percent EtOAc / hexane). Yield 11.5 g (77 percent).1H NMR (400 MHz, CHLOROFORM-^) delta ppm 11.62 (s, 1 H), 10.23 (s, 1 H), 7.42 – 7.16 (m, 5 H), 7.05 (dd, J=8.8, 5.3 Hz, 1 H), 6.54 (t, J=9.6 Hz, 1 H), 4.52 (s, 2 H), 4.13 (t, J=6.3 Hz, 2 H), 3.68 (t, J=6.1 Hz, 2 H), 2.12 (quin, J=6.2 Hz, 2 H). 19F NMR (376 MHz, CHLOROFORM- d): -132 ppm.

According to the analysis of related databases, 54314-84-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ANACOR PHARMACEUTICALS, INC.; HERNANDEZ, Vincent, S.; DING, Charles; PLATTNER, Jacob, J.; ALLEY, Michael Richard, Kevin; ROCK, Fernando; ZHANG, Suoming; EASOM, Eric; LI, Xianfeng; ZHOU, Ding; WO2012/33858; (2012); A2;,
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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. 19500-02-8, name is 3-Methoxy-2-methylaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C8H11NO

Example 2: Preparation ofN-[17-[2-(3-isopropylpyrazol-l-yl)-7-methoxy-8- methylquinolin-4-yloxy]- 13-methyl-2,14-dioxo-3,13-diazatricyclo[13.3.0.04’6]octadec- 7-ene -4-carbonyl] (dimethylamino)sulfonamide (29) .; Step 1: Synthesis of ethyl 4-hydroxy-7-methoxy-8-methylquinoline-3-carboxylate (11).; 10 EPO Diethyl ethoxymethylenemalonate (17.2 g, 79.6 mmol) was added to 2-methyl-m- anisidine (8.4 g, 61.2 mmol) (exothermic reaction). Then, diethylether (100 mL) was added and the mixture was stirred overnight at room temperature. The solvent was evaporated and the residue re-dissolved in ether (50 mL), filtered, washed with heptane and dried to give 12 g of an intermediate. This intermediate was added portion wise to diphenyl ether (50 mL) pre-heated at 230 0C. The reaction mixture was successively heated to 250 0C for 1.5 h, cooled at room temperature, and diluted with heptane (200 mL). The precipitate was filtered off, and successively washed with heptane and ether to give 9.2 g (57.5 percent) of the target product 11 as a yellow powder: m/z = 262 (M + H)+.

The synthetic route of 19500-02-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TIBOTEC PHARMACEUTICALS LTD.; MEDIVIR AB; WO2007/14925; (2007); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem