Month: June 2021

Application of 437-83-2, A common heterocyclic compound, 437-83-2, name is 3-Fluoro-2-methoxyaniline, molecular formula is C7H8FNO, 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 1[00180j To a stirred solution of Intermediate 1(0.33 g, 1.61 mmol) in DMA (3 mL) was added 3-fluoro-2-methoxyaniline (0.27 g, 1.9 mmol) followed by NaHMDS (1M in THF, 4.83mL, 4.83 mmol). The reaction was stirred for 30 minutes and then water (30 mL) was gradually added resulting in the product crashing out as a precipitate. The product was collected by filtration, washed with additional water and then dried undervacuum providing Intermediate 15 (476 mg, 95% yield). LC retention time 3.22 mm [A]. MS(Ej m/z: 310 (MHj.

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; MOSLIN, Ryan M.; LIN, Shuqun; WEINSTEIN, David S.; WROBLESKI, Stephen T.; ZHANG, Yanlei; TOKARSKI, John S.; WO2014/74660; (2014); 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 13070-45-6 as follows. HPLC of Formula: C13H15NO

Dissolve 93 mg of S11 in acetonitrile.Add 135 mg of 3,4-dihydroxybenzonitrile and add 7 mg of iron phthalocyanine under ice bath.30 mg of acetic acid, 4.8 mg of methanesulfonic acid and 135 mg of tert-butyl hydroperoxide, After stirring the reaction for 5 minutes under the same conditions,After monitoring the reaction, it was diluted with 20 mL of ethyl acetate and extracted with 20 mL of H2O.The combined organic layer Wash with 20 mL of saturated brine.Dry with anhydrous Na2SO4, filter and spin dry. Purified with silica gel column, eluent PE/ EtOAc = 8:1,188 mg of compound 11,The reaction yield was 56%;The product was a light yellow oil at room temperature.Physical state: light yellow oil; melting point: 138.5-139.4 C

According to the analysis of related databases, 13070-45-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Fuzhou University; Chen Haijun; Guo Mei; Ye Jinxiang; Chen Yi; Lin Yuqi; Gao Yu; (14 pag.)CN108530456; (2018); A;,
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Reference of 204452-91-5, 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. 204452-91-5, name is 7-(Dimethoxymethyl)-1,2,3,4-tetrahydro-1,8-naphthyridine, This compound has unique chemical properties. The synthetic route is as follows.

Compound 13c (0.73 g) was dissolved in trifluoroacetic acid (5 mL). The resulting mixture was allowed to stir at room temperature under argon for 1.5 hours. The mixture was concentrated. The residue was dissolved in methylene chloride and washed 2× with saturated sodium bicarbonate solution. The organic layer was dried over magnesium sulfate, filtered, and the filtrate was concentrated to obtain compound 13d.

The chemical industry reduces the impact on the environment during synthesis 7-(Dimethoxymethyl)-1,2,3,4-tetrahydro-1,8-naphthyridine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Flores, Christopher M.; Wade, Paul R.; US2011/319400; (2011); A1;,
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Electric Literature of 352-67-0,Some common heterocyclic compound, 352-67-0, name is 1-Fluoro-4-(trifluoromethoxy)benzene, molecular formula is C7H4F4O, 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 5: 7-bromo-3-[4-(trifluoromethoxy)phenyl]benzo[e]benzimidazole A stirred solution of the product of step 4 (15 g, 0.06 mol) and 1 -fluoro-4- (trifluoromethoxy)benzene (21 g, 0.12 mol) and Cs2C03 (50 g, 0.15 mol) in DMF (250 mL) was heated to 160C for 16h. The reaction mixture was diluted with water and extracted with EtOAc. The organic layer was dried (MgS04) and concentrated to give 7- bromo-3-[4-(trifluoromethoxy)phenyl]benzo[e]benzimidazole 16 g (65% yield) which was used without further purification. LC/MS (method 1 ): Rt = 1.304 min; MS: m / z = 406.7 (M+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Fluoro-4-(trifluoromethoxy)benzene, its application will become more common.

Reference:
Patent; BASF SE; NARINE, Arun; BANDUR, Nina Gertrud; DICKHAUT, Joachim; KOLLER, Raffael; VON DEYN, Wolfgang; WACH, Jean-Yves; SALGADO, Vincent; WO2015/7682; (2015); 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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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. Recommanded Product: 38336-04-8

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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Synthetic Route 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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Related Products of 494-99-5,Some common heterocyclic compound, 494-99-5, name is 1,2-Dimethoxy-4-methylbenzene, molecular formula is C9H12O2, 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.

1 ,2-Dimethoxy-5-methyl-3,4-dinitro-benzene was synthesized by adding 15.0 g of 3,4- dimethoxytoluene portionwise to a mixture of 60 mL fumic nitric acid and 300 mL water keeping the temperature < 200C with the aid of an ice bath. The reaction was stirred for 1 h at 00C, quenched by the addition of ice and stirred for another 1 h. The yellow solid was filtered off, washed with ice cold water and dried in vacuo to yield 9.2 g of 1 ,2-dimethoxy- 5-methyl-3,4-dinitro-benzene as yellow solid.1H-NMR (CDCI3): 6.88 (s, 1 H); 4.01 (s, 3H); 3.98 (s, 3H); 2.52 (s, 3H). These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,2-Dimethoxy-4-methylbenzene, its application will become more common. Reference:
Patent; ACTELION PHARMACEUTICALS LTD; WO2008/132679; (2008); A1;,
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Reference 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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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. name: 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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