Heterocyclic Building Blocks-Benzothiophene

360576-01-8, Methyl 6-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 750 mg of methyl 6-bromobenzo[b]thiophene-2-carboxylate, 438 mg of phenyl boronic acid, 610mg of lithium chloride, 528 mg of sodium carbonate, 160 mg of tetrakis(triphenylphosphine)palladium (0), 30 ml of 1,4-dioxane, and 15 ml of water was stirred for 4 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 475 mgof methyl 6-phenylbenzo[b]thiophene-2-carboxylate.

As the paragraph descriping shows that 360576-01-8 is playing an increasingly important role.

Reference£º
Patent; Sumitomo Chemical Company Limited; MUKUMOTO, Fujio; TAMAKI, Hiroaki; KUSAKA, Shintaro; IWAKOSHI, Mitsuhiko; EP2926660; (2015); A1;,
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4923-87-9, 5-Bromobenzothiophene is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of 5-bromo-1-benzothiophene (2 g, 9.385 mmol), phenylboronic acid (1.2 g, 9.841 mmol), Pd(PPh3)4, (544 g, 0.471 mmol), potassium carbonate (1.9 g, 13.747 mmol) in toluene and water (20+20 mL) mixture was refluxed at 100C for overnight. After completion of the reaction, the mixture was cooled to room temperature, diluted with ethyl acetate, filtered through a Celite bed, and washed with ethyl acetate. The combined filtrate was washed with water and brine. The organic layer was dried over sodium sulfate and concentrate under reduced pressure to give residue which was purified by column chromatography using hexane as eluent on silica gel to afford 5-phenyl-1-benzothiophene (1.7 g, 8.084 mmol, 86%) as white solid. ?H-NMR (400 MHz, CDC13): oe 7.95 (d, J=l.5 Hz, 1H), 7.86 (dd, J?=8.5 Hz, J?0.7 Hz, 1H), 7.60-7.58 (m, 2H), 7.52 (dd, J?=8.3 Hz, J?=1.7 Hz, 1H), 7.41-7.37 (m, 3H), 7.32-7.27 (m, 2H).

4923-87-9 5-Bromobenzothiophene 2776578, abenzothiophene compound, is more and more widely used in various.

Reference£º
Patent; CURADEV PHARMA PRIVATE LTD.; BANERJEE, Monali; MIDDYA, Sandip; SHRIVASTAVA, Ritesh; RAINA, Sushil; SURYA, Arjun; YADAV, Dharmendra B.; YADAV, Veejendra K.; KAPOOR, Kamal Kishore; VENKATESAN, Aranapakam; SMITH, Roger A.; THOMPSON, Scott K.; WO2014/186035; (2014); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1423-61-6,7-Bromobenzo[b]thiophene,as a common compound, the synthetic route is as follows.

Under a nitrogen stream, 12.2g of (35.2mmol) 7-bromobenzo[b]thiophene,6.44g of (38.7mmol) 2-nitrophenylboronic acid, 4.22g (10Put the THF / H2O of NaOH and 300ml / 150ml of 5.6mmol), stirring, Pd(PPh3)4 of 2.03g (5mol%) at 40 C, 12 hat 80 C During the mixture was stirred. After completion of the reaction, and extracted with methylene chloride, put MgSO4, and filtered.After removal of the solvent of the filtered organic layer, using column chromatography to give 7-(2-nitrophenyl)benzo[b]thiophene 7.38g (28.9mmol, yield: 82%).

The synthetic route of 1423-61-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; DOOSAN CORPORATION; KIM, HOE MOON; KIM, SUNG MOO; KIM, YOUNG BAE; KIM, TAE HYUNG; PARK, HO CHEOL; LEE, CHANG JUN; BACK, YOUNG MI; SHIN, JIN YONG; (222 pag.)JP2016/40292; (2016); A;,
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5381-20-4, Thianaphthene-3-carboxaldehyde is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of thianaphthene-3-carboxaldehyde (0.104 g, 0.64 mmol), 3-aminocrotonitrile (0.052 g, 0.64 mmol), benzoylacetonitrile (0.0897 g, 0.62 mmol) and acetic acid (0.035 mL, 0.64 mmol) in isopropyl alcohol (3.5 mL) was heated to 100C and left to stir for 16 hours. The mixture was allowed to cool to RT and concentrated. The residue was basified with aq. sodium bicarbonate, and the resulting solid was filtered off and purified by column chromatography (3:1 Hexane: Ethyl acetate) rendering a light-yellow solid (0.0162 g, 7 %). 1H-NMR (400 MHz, DMSO-d6) delta = 2.12 (s, 3H), 5.17 (s, 1H), 7.39-7.49 (m, 2H), 7.50-7.59 (m 5H), 7.78 (s, 1H), 8.01 (dd, 1H), 8.06 (dd, 1H), 9.92 (s, 1H). HPLC-MS: Rt 4.329 min, m/z 354.1 (MH+). The following examples were synthesized according to Method F.

5381-20-4 Thianaphthene-3-carboxaldehyde 227328, abenzothiophene compound, is more and more widely used in various.

Reference£º
Patent; Oncostellae, S.L.; KURZ, Guido; CAMACHO GOMEZ, Juan; (123 pag.)EP3480201; (2019); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.5381-20-4,Thianaphthene-3-carboxaldehyde,as a common compound, the synthetic route is as follows.

General procedure: To a solution of an aromatic aldehyde 1 (0.500 mmol, 1.0 equiv) and TMSN3 (115 mg, 1.00 mmol,2.0 equiv) in a premixed HFIP/ACN mixture (2.0 mL, 1:1) in a nitrogen-flushed two dram vial wasadded triflic acid (TfOH; 17.7 L, 0.200 mmol, 0.40 equiv) (exotherm and brisk effervescence due tonitrogen gas evolution was immediately observed). The vial was capped and the reaction mixture wasallowed to stir at rt for 20-75 min. The reaction mixture was concentrated under nitrogen. The residueobtained was suspended in CH2Cl2/hexanes mixture and loaded on a silica gel in a 5 g samplecartridge. Purification using a normal phase silica flash column on a CombiFlash purification systemafforded a corresponding aromatic nitrile 2 upon concentration of appropriate fractions.

5381-20-4 Thianaphthene-3-carboxaldehyde 227328, abenzothiophene compound, is more and more widely used in various.

Reference£º
Article; Motiwala, Hashim F.; Yin, Qin; Aube, Jeffrey; Molecules; vol. 21; 1; (2016);,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.4923-87-9,5-Bromobenzothiophene,as a common compound, the synthetic route is as follows.

In a 100 mL screwcapped vessel 5-bromobenzo[b]thiophene (2.30 g, 10.8 mmol) was dissolved in acetone (46 ml). Oxone, monopersulfate (potassium peroxymonosulfate) (27.0 g, 43.2 mmol) and water were added and stirred at 70 C overnight. To the reaction mixture water and ethyl acetate were added. The organic layer was separated, dried, filtered and the solvent was evaporated to dryness. The yellow residue was purified by flash-chromatography (n-heptane/DCM) to give 769 mg (29 %) of the title compound as a white solid. Rt = 2.393 min (HPLC method A).

4923-87-9 5-Bromobenzothiophene 2776578, abenzothiophene compound, is more and more widely used in various.

Reference£º
Patent; MERCK PATENT GMBH; CANCER RESEARCH TECHNOLOGY LIMITED; SCHIEMANN, kai; STIEBER, Frank; BLAGG, Julian; MALLINGER, Aurelie; WAALBOER, Dennis; RINK, Christian; CRUMPLER, Simon Ross; WO2014/63778; (2014); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.154650-81-4,Benzo[b]thiophene-6-carbonitrile,as a common compound, the synthetic route is as follows.

A mixture of compound B-199 (2.6 g, 16 mmol) in 4N hydrochloric acid (30 mL) was stirred at 100 C for 5 hours. On completion, the reaction mixture was cooled to 0 C, and the solid was collected by filtration. The residue was dried in vacuo to give compound B-200 (2.4 g, 83% yield) as a yellow solid.

As the paragraph descriping shows that 154650-81-4 is playing an increasingly important role.

Reference£º
Patent; FORUM PHARMACEUTICALS, INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; MCRINER, Andrew, J.; WO2015/66371; (2015); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.5381-20-4,Thianaphthene-3-carboxaldehyde,as a common compound, the synthetic route is as follows.

3-Benzo[b]thiophen-3-yl-acrylic acid A suspension of 1-benzothiophene-3-carbaldehyde (4.9 g, 0.03 mol), malonic acid (6.6 g, 0.06 mol) and piperidine (1 mL) in 100 mL anhydrous pyridine was heated at 110 C. overnight. The reaction mixture was cooled to room temperature and the solvent was removed in vacuo. The residue was taken up in 100 mL of water and 1 N hydrochloric acid was added to adjust the pH of this solution to ca. 3. The suspension was filtered and the yellow solid was collected, washed with water (3*50 mL) and concentrated in vacuo to give the indicated product with 95% purity (5.65 g, 91%).

5381-20-4 Thianaphthene-3-carboxaldehyde 227328, abenzothiophene compound, is more and more widely used in various.

Reference£º
Patent; Chaturvedula, Prasad V.; Chen, Ling; Civiello, Rita; Conway, Charles Mark; Degnan, Andrew P.; Dubowchik, Gene M.; Han, Xiaojun; J. Jiang, Xiang Jun; Karageorge, George N.; Luo, Guanglin; Macor, John E.; Poindexter, Graham; Tora, George; Vig, Shikha; US2004/204397; (2004); A1;,
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Benzothiophene | C8H6S – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.5381-20-4,Thianaphthene-3-carboxaldehyde,as a common compound, the synthetic route is as follows.

Diethyl(phenanthren-9-ylmethyl)phosphonate (11 g, 33.5 mmol) and 3-carbaldehydebenzo[b]thiophene (5.5 g, 33.5 mmol) were dissolved in 250 mL of 1,2-dimethoxyethane. The mixture was cooled to 0 C. and NaH (6 g, 150 mmol) was added in portions. The reaction mixture was warmed to room temperature and heated to reflux for 2.5 h. The reaction mixture was concentrated and the residue was purified by silica gel column chromatography (30% CH2Cl2 in hexane) to yield 6 g of product. Synthesis of benzo[b]triphenyleno[2,1-d]thiophene.

5381-20-4 Thianaphthene-3-carboxaldehyde 227328, abenzothiophene compound, is more and more widely used in various.

Reference£º
Patent; Universal Display Corporation; US2011/266526; (2011); A1;,
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Benzothiophene | C8H6S – PubChem

346592-74-3, 7-Fluorobenzo[b]thiophene is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

2-Fluorothiophenol (4.14 g, 32.6 mmol) was dissolved in anhydrous THF (100 mL). Potassium tert-butoxide (1.0 M in THF, 35.8 mL) was added and the suspension was stirred at room temperature for 15 minutes. 2-Chloroacetaldehyde dimethyl acetal was added and the mixture was stirred for 3 days. Water (100 mL) was added and the solution was extracted with diethyl ether (3¡Á100 mL). The extracts were concentrated to a yellow oil and chromatographed (5 to 20% ethyl acetate in hexane) to yield 1-(2,2-dimethoxy-ethylsulfanyl)-2-fluoro-benzene (6.42 g) as a colorless oil. Chlorobenzene (25 mL) was heated to reflux and polyphosphoric acid (1 mL) was added. The 1-(2,2-dimethoxy-ethylsulfanyl)-2-fluoro-benzene was then added slowly turning the solution dark. After 3 hours of heating, the reaction was cooled to room temperature and diluted with water (50 mL). The solution was extracted with benzene (2¡Á50 mL). The extracts were concentrated and chromatographed (0 to 15% ethyl acetate in hexane) to yield 7-fluorobenzothiophene (0.77 g). The 7-fluorobenzothiophene (0.77 g, 5.1 mmol) and dichloromethyl methyl ether (0.872 g, 7.6 mmol) were dissolved in anhydrous DCM (25 mL). Titanium tetrachloride (1.0 M in DCM, 7.6 mL, 7.6 mmol) was added, turning the solution dark. After 30 minutes at room temperature, the reaction was poured into a mixture of saturated aqueous NaHCO3 and ice. The mixture was stirred for about 30 minutes and then was extracted with DCM (2¡Á50 mL). The extracts were concentrated and chromatographed (0 to 15% ethyl acetate in hexane) to yield 7-fluorobenzothiophene-3-carboxaldehyde (0.642 g). The 7-fluorobenzothiophene-3-carboxaldehyde (0.642 g, 3.77 mmol) and sulfamide (1.7 g, 18 mmol) were combined in anhydrous ethanol (20 mL) and heated to reflux for three days. The reaction was cooled to room temperature and sodium borohydride (0.148 g, 3.92 mmol) was added. After two hours, water (25 ml) was added and the solution was extracted with chloroform (3¡Á25 mL). The extracts were concentrated, suspended in a minimal amount of DCM, and filtered to yield the title compound as a yellow solid.1H NMR (DMSO-d6): delta 7.78 (1H, d, J=8.0 Hz), 7.43-7.50 (1H, m), 7.27 (1H, dd, J=10.3, 7.9 Hz), 7.14 (1H, t, J=6.4 Hz), 6.74 (2H, br s), 4.31 (2H, d, J=6.4 Hz).

The synthetic route of 346592-74-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Smith-Swintosky, Virginia L.; US2007/191460; (2007); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem