Some tips on 360575-29-7

The synthetic route of 360575-29-7 has been constantly updated, and we look forward to future research findings.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.360575-29-7,Methyl 4-bromobenzo[b]thiophene-2-carboxylate,as a common compound, the synthetic route is as follows.

12202] A mixture of 353 mg of methyl 4-bromobenzo[b] thiophene-2-carboxylate, 217 mg of 2-thiophene boronic acid, 287 mg of lithium chloride, 248 mg of sodium carbonate, 75 mg of tetrakis(triphenylphosphine)palladium (0), 10 ml of 1 ,4-dioxane, and 5 ml of water was stirred for 3 hours at 100 C. under a nitrogen atmosphere. After being cooled to room temperature, the reaction mixture was concentrated under reduced pressure. Chloroform and water were added to the residues, and insoluble matter was separated by filtration. The aqueous layer was extracted twice by using chloroform, and the collected organic layer was washed with saturated saline, dried over magnesium sulfate, and then concentrated under reduced pressure. The residues were subjected to silica gel colunm chromatography, thereby obtaining 350 mg of methyl 4-(2-thienyl)benzo[b]thiophene-2-carboxylate (hereinafier, described as a ?compound 52 of the present invention?).12203] Compound 52 of the Present Invention 12204] ?H-NMR (CDC13) oe: 8.42 (s, 1H), 7.84-7.82 (m,1H), 7.51-7.48 (m, 2H), 7.44-7.42 (m, 1H), 7.36-7.35 (m,1H), 7.20-7.18 (m, -1H), 3.95 (s, 3H)., 360575-29-7

The synthetic route of 360575-29-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; Mukumoto, Fujio; Tamaki, Hiroaki; Kusaka, Shintaro; Iwakoshi, Mitsuhiko; US2015/282482; (2015); A1;,
Benzothiophene – Wikipedia
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Downstream synthetic route of 360575-29-7

The synthetic route of 360575-29-7 has been constantly updated, and we look forward to future research findings.

360575-29-7, Methyl 4-bromobenzo[b]thiophene-2-carboxylate is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

12151] A mixture of 750 ng of methyl 4-bromobenzo[b] thiophene-2-carboxylate, 438mg of phenyl boronic acid, 610 mg of lithium chloride, 528mg of sodium carbonate, 160mg of tetrakis(triphenylphosphine)palladium (0), 30 ml of 1,4- dioxane, and 15 ml of water was stirred for 4 hours at 1000 C. under nitrogen atmosphere. After being cooled to room temperature, the reaction mixture was concentrated under reduced pressure. Chloroform and water were added to the residues, and insoluble matter was separated by filtration. The aqueous layer was extracted twice by using chloroform, and the collected organic layer was washed with saturated saline, dried over magnesium sulfate, and then concentrated under reduced pressure. The residues were subjected to silica gel column chromatography, thereby obtaining 477mg of methyl 4-phenylbenzo[b]thiophene-2-carboxylate (hereinafier, described as a ?compound 34 of the present invention?).12152] Compound 34 of the Present Inventionj2153] ?H-NMR (CDC13) oe: 8.17-8.16 (m, 1H), 7.87-7.85 (m, 1H), 7.57-7.48 (m, 5H), 7.47-7.42 (m, 1H), 7.41-7.39 (m, 1H), 3.93 (s, 3H)., 360575-29-7

The synthetic route of 360575-29-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; Mukumoto, Fujio; Tamaki, Hiroaki; Kusaka, Shintaro; Iwakoshi, Mitsuhiko; US2015/282482; (2015); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

 

Brief introduction of 360575-29-7

As the paragraph descriping shows that 360575-29-7 is playing an increasingly important role.

360575-29-7, Methyl 4-bromobenzo[b]thiophene-2-carboxylate is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of 500 mg of methyl 4-bromobenzo[b]thiophene-2-carboxylate, 161 mg of methylboronic acid, 1.17g of potassium phosphate, 151 mg of a [1,1?-bis(diphenylphosphino)ferrocene]palladium (II) dichloride dichloromethaneadduct, and 6 ml of 1,4-dioxane, and 0.1 ml of water was stirred for 3 hours at 100C under a nitrogen atmosphere. Afterbeing cooled to room temperature, the reaction mixture was concentrated under reduced pressure. Chloroform andwater were added to the residues, and insoluble matter was separated by filtration. The filtrate was extracted usingchloroform, and the organic layer was washed with saturated saline, dried over magnesium sulfate, and then concentratedunder reduced pressure. The residues were subjected to silica gel column chromatography, thereby obtaining 340 mgof methyl 4-methylbenzo[b]thiophene-2-carboxylate., 360575-29-7

As the paragraph descriping shows that 360575-29-7 is playing an increasingly important role.

Reference£º
Patent; Sumitomo Chemical Company Limited; MUKUMOTO, Fujio; TAMAKI, Hiroaki; KUSAKA, Shintaro; IWAKOSHI, Mitsuhiko; EP2926660; (2015); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

 

New learning discoveries about 360575-29-7

Big data shows that 360575-29-7 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.360575-29-7,Methyl 4-bromobenzo[b]thiophene-2-carboxylate,as a common compound, the synthetic route is as follows.

To a suspension of sodium hydride (55%, 1.11 g) in dimethyl sulfoxide (20 mL) was added methyl thioglycolate (1.53 mL) at room temperature, and the mixture was stirred for 15 minutes. A solution of 2-bromo-6-fluorobenzaldehyde (3.43 g) in dimethyl sulfoxide (4mL) was added to the reaction mixture, and the mixture was stirred at room temperature for 5 minutes. The reaction mixture was poured into water with ice and precipitated crystalline solid was collected by filtration, washed with water and dried under reduced pressure to give 2-methoxycarbonyl-4-bromobenzo-[b]thiophene (1.52 g). This material was suspended in a mixed solvent of methanol (20 mL) and water (10 mL) and sodium hydroxide (0.91 g) was added to the suspension. The mixture was stirred for at 50C for 5 hours. The reaction mixture was cooled with ice bath, and the reaction mixture was acidified by adding 2mol/L hydrochloric acid. The precipitated crystalline solid was collected by filtration, washed with water and dried under reduced pressure to give 2-carboxybenzo[b]thiophene (1.27 g). To this material were added copper powder (0.42 g) and quinoline (10 mL), and the mixture was stirred at 190C for 1 hour. After the reaction mixture was cooled to room temperature, 2mol/L hydrochloric acid (40mL) and ethyl acetate (20 mL) were added to the reaction mixture, and the mixture was stirred for 15 minutes. Insoluble material in the mixture was removed by filtration, and the organic layer of the filtrate was separated. The aqueous layer of filtrate was extracted with ethyl acetate. The organic layers were combined, and the combined organic layer was washed with 2mol/L hydrochloric acid, water and brine and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane) to give the title compound (0.55 g). 1H-NMR (CDCl3) delta ppm: 7.15-7.25 (1H, m), 7.45-7.6 (3H, m), 7.82 (1H, d, J=8.2Hz), 360575-29-7

Big data shows that 360575-29-7 is playing an increasingly important role.

Reference£º
Patent; Kissei Pharmaceutical Co., Ltd.; EP1724277; (2006); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

 

Analyzing the synthesis route of 360575-29-7

As the paragraph descriping shows that 360575-29-7 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.360575-29-7,Methyl 4-bromobenzo[b]thiophene-2-carboxylate,as a common compound, the synthetic route is as follows.

General procedure: The solution of compound 2a-2n (1.1 mmol) in water (10 mL)was stirred and then potassium hydroxide pellets (5.4 mmol) wereadded, which was refluxed for 3 h. The aqueous layer was thenacidified to pH 1 with 1M hydrochloric acid solution. The aqueouslayer was extracted with dichloromethane (3 x 15 mL). The combinedorganic layers were dried with sodium sulfate, filtered, andthe solvents were removed under reduced pressure to afford thetitle compound 3a-3n [31,34]. 4.1.2.1. 4-bromobenzo[b]thiophene-2-carboxylic acid (3a). Yield 97%, white solid; m. p. 140-143 C; 1H NMR (600 MHz, DMSO-d6)delta 13.78 (s, 1H), 8.10 (d, J = 8.2 Hz, 1H), 7.96 (s, 1H), 7.71 (d, J = 7.7 Hz,1H), 7.44 (dt, J = 13.1, 2.7 Hz, 1H)., 360575-29-7

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Reference£º
Article; Cai, Guiping; Yu, Wenying; Song, Dongmei; Zhang, Wenda; Guo, Jianpeng; Zhu, Jiawen; Ren, Yuhao; Kong, Lingyi; European Journal of Medicinal Chemistry; vol. 174; (2019); p. 236 – 251;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

 

Some tips on 360575-29-7

The synthetic route of 360575-29-7 has been constantly updated, and we look forward to future research findings.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.360575-29-7,Methyl 4-bromobenzo[b]thiophene-2-carboxylate,as a common compound, the synthetic route is as follows.

After dissolving methyl 4-bromobenzo [b] thiophene-2-carboxylate (1 eq) in dimethylene glycol ether (DME), tetrakis (triphenylphosphine) palladium (0) (Pd (PPh3) 4, 0.02 eq), 4-fluorophenylboronic acid (1.1 eq) and 2M sodium carbonate (2M Na2CO3, 5 eq) The mixture was stirred at 60 DEG C for 5 hours. The reaction solution was cooled to room temperature, filtered through Celite, and the reaction filtrate was washed with water and EtOAc and extracted. A small amount of water in the organic layer was removed with anhydrous MgSO 4, the solvent was removed by distillation under reduced pressure, and the product was separated into a column to obtain the target compound in 92% yield., 360575-29-7

The synthetic route of 360575-29-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Chungnam National University Industry-Academic Cooperation Foundation; Kim, Uhn Hee; Yu, Sung Uhn; Kang, Nam Sook; Ku, Tae Sung; Park, Min Young; Kim, Young Hun; Bae, Hyun Ju; Kim, Jin Woo; In, Tae Gyu; Ju, Chun Gi; (44 pag.)KR101515985; (2015); B1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

 

Downstream synthetic route of 360575-29-7

Big data shows that 360575-29-7 is playing an increasingly important role.

360575-29-7, Methyl 4-bromobenzo[b]thiophene-2-carboxylate is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of 353 mg of methyl 4-bromobenzo[b]thiophene-2-carboxylate, 217 mg of 2-thiophene boronic acid,287 mg of lithium chloride, 248 mg of sodium carbonate, 75 mg of tetrakis(triphenylphosphine)palladium (0), 10 ml of1,4-dioxane, and 5 ml of water was stirred for 3 hours at 100C under a nitrogen atmosphere. After being cooled to roomtemperature, the reaction mixture was concentrated under reduced pressure. Chloroform and water were added to theresidues, and insoluble matter was separated by filtration. The aqueous layer was extracted twice by using chloroform,and the collected organic layer was washed with saturated saline, dried over magnesium sulfate, and then concentratedunder reduced pressure. The residues were subjected to silica gel column chromatography, thereby obtaining 350 mgof methyl 4-(2-thienyl)benzo[b]thiophene-2-carboxylate., 360575-29-7

Big data shows that 360575-29-7 is playing an increasingly important role.

Reference£º
Patent; Sumitomo Chemical Company Limited; MUKUMOTO, Fujio; TAMAKI, Hiroaki; KUSAKA, Shintaro; IWAKOSHI, Mitsuhiko; EP2926660; (2015); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

 

Brief introduction of 360575-29-7

As the paragraph descriping shows that 360575-29-7 is playing an increasingly important role.

360575-29-7, Methyl 4-bromobenzo[b]thiophene-2-carboxylate is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of 300 mg of methyl 4-bromobenzo[b]thiophene-2-carboxylate, 100 mg of lithium hydroxide monohydrate,3 ml of water, and 9 ml of methanol was stirred for 2 hours at 75C. The reaction mixture was concentratedunder reduced pressure, water was added to the residues, and the residue was washed three times with tert-butyl methylether. Concentrated hydrochloric acid was added to the aqueous layer, and then extraction was performed three timesby using tert-butyl methyl ether. The collected organic layer was washed with saturated saline, dried over magnesiumsulfate, and then concentrated under reduced pressure, thereby obtaining 270 mg of 4-bromobenzo[b]thiophene-2-carboxylic acid (hereinafter, described as a “compound 10 of the present invention”). Compound 10 of the presentinvention 1H-NMR (DMSO-D6) delta: 13.79 (br s, 1H), 8.11 (dd, 1H, J = 7.8, 0.8 Hz), 7.97 (s, 1H), 7.73 (dd, 1H, J = 7.8, 0.8 Hz), 7.46(t, 1H, J = 7.8 Hz).

As the paragraph descriping shows that 360575-29-7 is playing an increasingly important role.

Reference£º
Patent; Sumitomo Chemical Company Limited; MUKUMOTO, Fujio; TAMAKI, Hiroaki; KUSAKA, Shintaro; IWAKOSHI, Mitsuhiko; EP2926660; (2015); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem