Category: benzothiophene

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, brs), 4.31 (2H, d, J=6.4 Hz).

As the paragraph descriping shows that 346592-74-3 is playing an increasingly important role.

Reference£º
Patent; Smith-Swintosky, Virginia L.; Parker, Michael H.; Reitz, Allen B.; Maryanoff, Bruce E.; US2007/293476; (2007); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

89673-36-9, tert-Butyl benzo[b]thiophen-2-ylcarbamate is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

benzo[b]thiophen-2-ylamine hydrochloride (1-C). Compound 1-B (1.45 g, 5.81 mmol) was added to a solution of HCl in dioxane (4 N, 20 mL), and the mixture was stirred at rt until all the starting material was consumed. The mixture was diluted with diethyl ether, the product collected by filtration, and washed with diethyl ether, to afford compound 1-C as an off-white solid (0.89 g, 83%). 1H-NMR (DMSO-d6): delta 6.43 (s, 1H), 6.8-7.2 (br s, 3H) superimposed on 7.05 (m, 1H) and 7.20 (m, 1H), 7.45 (d, 1H), 7.66 (d, 1H); MS: m/z 150.1 (MH+).

The synthetic route of 89673-36-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Branum, Shawn T.; Colburn, Raymond W.; Dax, Scott L.; Flores, Christopher M.; Jetter, Michele C.; Liu, Yi; Ludovici, Donald; Macielag, Mark J.; Matthews, Jay M.; McNally, James J.; Reaney, Laura M.; Russell, Ronald K.; Qin, Ning; Teleha, Christopher; Wells, Kenneth M.; Youells, Scott C.; Youngman, Mark A.; US2012/190674; (2012); A1;,
Benzothiophene – Wikipedia
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.

Mix an aliquot (1 niL) of a 0.25 M solution of (S)-[l-(6-fluoropyridin-3-yl)- pyrrolidin-3-yl] -amine (0.25 mmol) in toluene, an aliquot (1 mL) of a 1.0 M solution of benzo [delta]thiophene-3-carboxaldehyde (1.0 mmol) in toluene and add a single activated 4A molecular sieve. Stir the reactants at room temperature in air. After 16 h add PS- Trisamine (1.5 mmol) and another single activated 4A molecular sieve. Stir the reactants at room temperature in air. After 24 h filter the reaction solution to remove the PS- Trisamine, and add an aliquot (2 mL) of a 0.25 M solution of sodium borohydride (0.5 mmol) in ethanol. Stir the reactants at room temperature in air. After 48 h add methanol (2 mL) to the reactants and agitate vigorously. Remove the excess reactants by ion- exchange chromatography using a 5g SCX-2 cartridge (0.5 mmol/g SO3H) by wetting it with one column volume of methanol. Apply the mixture to the cartridge and allow it to percolate through the stationary phase (under gravity) into a vial. Wash the cartridge with one column volume of methanol such that these washings also pass into the vial. Replace with a second vial and elute with 3.5N ammonia in methanol (10 mL). Evaporate the solvents from the ammonia washings on a heating block under a stream of nitrogen to give the title compound. 1H NMR (400 MHz, DMSOd6) delta 7.90-7.98 (2H, m)5 7.57 (IH, s), 7.39-7.42 (IH, m), 7.35-7.39 (2H, m), 7.08-7.13 (IH5 m), 6.96 (IH5 dd, J = 8.93, 3.30 ‘ Hz), 4.01 (2H5 S)5 3.43-3.50 (2H5 m), 3.20-3.27 (IH5 m), 3.17 (IH5 d, J = 5.14 Hz)5 3.07- 3.13 (IH5 m), 2.10-2.18 (IH5 m), 1.87-1.95 (IH5 m), MS (ES): m/z = 328 [M+H].

The synthetic route of 5381-20-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ELI LILLY AND COMPANY; WO2006/44454; (2006); A1;,
Benzothiophene – Wikipedia
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.

General procedure: The mixture of the compound 15 (190.2 mg, 1.0 mmol) and 2-thiophenecarboxaldehyde (123.4 mg, 1.1 mol) in anhydrous ethanol (3.0 mL) was stirred over night at room temperature or reflux temperature. The corresponding imine was reduced with solid sodium borohydride (75.7 mg, 2.0 mmol) which was added slowly, the mixture was further stirred over night at room temperature. An additional ethanol (2.0 mL) was added to the reaction vessel after which 10% hydrochloric acid aqueous solution was added to quench excess sodium borohydride. The acidic mixture was basified with 25% aqueous ammonia solution. The desired product was extracted with dichloromethane (3 20 mL) and the solution was dried over sodium sulphate anhydrous. The solvent was removed under reduced pressure and the residue was purified by flash chromatography on silica gel, eluting with a gradient of 40-60% ethyl acetate in petroleum ether to give the title compound 17a1 [164.9 mg, 57.6% (from 15)] as a white solid, mp 100-101 C.

The synthetic route of 5381-20-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Zhong, Zhao-Jin; Zhang, Da-Jun; Peng, Zong-Gen; Li, Yu-Huan; Shan, Guang-Zhi; Zuo, Li-Min; Wu, Lin-Tao; Li, Si-Yang; Gao, Rong-Mei; Li, Zhuo-Rong; European Journal of Medicinal Chemistry; vol. 69; (2013); p. 32 – 43;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

5381-20-4, Thianaphthene-3-carboxaldehyde is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Potassium hydroxide (3.11 g) and water (0.12 ML) are added to acetonitrile (50 ML). TRIMETHYLSULFONIUM iodide (5.65 g) and thianapthene-3-carboxaldehyde (4.50 g) are then added. The reaction mixture is heated to 60 C for 4 h. The reaction mixture is allowed to cool to room temperature and is then diluted with Et20 (25 ML). The precipitate is filtered off, and the filtrate is concentrated in vacuo. The resulting crude epoxide (6.20 g) is dissolved in methanol (40 ML) and added to a 2.0 M solution of methyl amine in methanol (100 mL). The reaction mixture is stirred at room temperature for 3 d. The reaction mixture is concentrated in vacuo. The resulting brown oil is PURIFIED VIA COLUMN CHROMATOGRAPHY (CHCL3/METHANOL, 95/5,90/10 ; CHC13/METHANOINI-LOH, 90/10/1) to yield 1.753 g of the title compound as a yellow solid. Physical characteristics. M. p. 98-102C ; 1H NMR (400 MHz, DMSO-d6) 8 7.98-7. 90,7. 51,7. 60, 7.40-7. 33,5. 43,5. 04,2. 80, 2.34 ; MS (ESI+) m/z 208 (M+H) +.

As the paragraph descriping shows that 5381-20-4 is playing an increasingly important role.

Reference£º
Patent; PHARMACIA & UPJOHN COMPANY; WO2004/106345; (2004); A2;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

95-15-8, Thianaphthene is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: A dried and argon-flushed Schlenk tube is charged with the correspondingsubstrate (1.0 mmol, 1.0 equiv) and dissolved in THF(1.0 mL). TMP2Mn¡¤2MgCl2¡¤4LiCl (1.5 mL, 0.6 mmol, 0.6 equiv,0.40 M solution in THF) is added dropwise at the given temperatureand stirred until a reaction aliquot quenched withiodine in THF showed full consumption of the starting material.Then, the reaction mixture is cooled to the given temperature,and chloranil (1.0 mmol, 1.0 equiv) dissolved in THF (4.0 mL) isadded dropwise. The reaction is stirred for 0.5 h and is thenquenched with sat. aq NH4Cl solution and extracted with CH2Cl2(3 ¡Á 25 mL). The crude product is purified by column chromatographyon silica to yield the corresponding title compound

As the paragraph descriping shows that 95-15-8 is playing an increasingly important role.

Reference£º
Article; Haas, Diana; Hammann, Jeffrey M.; Moyeux, Alban; Cahiez, Gerard; Knochel, Paul; Synlett; vol. 26; 11; (2015); p. 1515 – 1519;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.146137-92-0,Methyl 5-(trifluoromethyl)benzo[b]thiophene-2-carboxylate,as a common compound, the synthetic route is as follows.

A mixture of 300 mg of methyl 5- ( trifluoromethyl ) benzo [ b] thiophene-2-carboxylate, 66 mg of lithium hydroxide monohydrate, 2 ml of water and 6 ml of methanol was stirred at 75C for 1 hour. The reaction mixture was cooled to room temperature, and then concentrated under reduced pressure. To the residue was added water, and then washed with tert-butyl methyl ether 3 times. To the aqueous layer was added concentrated hydrochloric acid, and then extracted with tert- butyl methyl ether 3 times. The combined organic layer was washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, and then concentrated under reduced pressure to obtain 280 mg of 5-(trifluoromethyl) benzo[ b] thiophene-2-carboxylic acid (the present compound 1) .[ The present compound 1]1H-NMR(CDC13 ) delta: 8.24(s, 1H) , 8.21(s, 1H) , 8.02 (d, J=8.7Hz, 1H) , 7.72 (d, J=8.7Hz, 1H)

As the paragraph descriping shows that 146137-92-0 is playing an increasingly important role.

Reference£º
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; MUKUMOTO, Fujio; TAMAKI, Hiroaki; IWAKOSHI, Mitsuhiko; KUSAKA, Shintaro; WO2012/153861; (2012); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

5381-20-4, Thianaphthene-3-carboxaldehyde is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

3-Benzo[b]thiophen-3-yl-3-hydroxy-propionitrile. (0168) To a stirring solution of diisopropylamine (0.93 mL, 6.58 mmol) in tetrahydrofuran (8 mL) at -78 C. under nitrogen was added a solution of n-butyllithium (2.75 mL, 6.88 mmol, 2.5 M in hexane). After the addition was complete, the mixture was stirred at -78 C. for 10 minutes and removed cooling bath for 5 minutes. The mixture was cooled back to -78 C., acetonitrile (0.31 mL, 5.98 mmol) was added and the reaction mixture was then stirred at -78 C. for 30 minutes. Benzo[b]thiophene-3-carbaldehyde (1 g, 5.98 mmol) in tetrahydrofuran (4 mL) was added and the resulting solution was allowed to warm to ambient temperature. After 18 hours at ambient temperature, saturated aqueous ammonium chloride (5 mL) was added to the reaction mixture and it was concentrated at reduced pressure. The resulting crude product was diluted with ethyl acetate (20 mL), washed with water (10 mL) followed by saturated aqueous sodium chloride (10 mL). The organic layer was concentrated and purified by column chromatography (80 g silica gel cartridge) eluting with ethyl acetate/hexane (30%-50%) to give the product as a light yellow oil (1.2 g, 99%).

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

Reference£º
Patent; Fox Chase Chemical Diversity Center, Inc.; Advanced Neural Dynamics, Inc.; Smith, Garry Robert; Brenneman, Douglas E.; Reitz, Allen B.; Zhang, Yan; Du, Yanming; US8609849; (2013); B1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.3541-37-5,Benzo[b]thiophene-2-carboxaldehyde,as a common compound, the synthetic route is as follows.

1 g of 4-bromophenylacetonitrile (5.1 mmol) and 825 mg ofbenzo[b]thiophene-2-carboxaldehyde (5.1 mmol) were dissolvedin dry MeOH (30 mL) and stirred at 0 C for 5 min 380 mg of odium methoxide (7.1 mmol) were added in small portions, and themixture was stirred for 15 min at 0 C and then for 4 h at roomtemperature. The resulting precipitate was collected using a sinteredglass filter, washed with 10 mL of MeOH, then with water anddried to give 1.56 g of the alpha,beta-unsaturated nitrile 7 as a yellow solid(90%); Rf 0.36 (cyclohexane/EtOAc, 90:10); m.p 160-162 C ; 1HNMR (300 MHz, CDCl3): d (ppm): 7.37-7.45 (m, 2H), 7.52-7.60 (m,4H), 7.69 (s, 1H, Hvinyl), 7.82-7.87 (m, 3H); 13C NMR (75 MHz,CDCl3): delta(ppm): 109.68 (C), 117.35 (CN), 122.43 (CH), 123.58 (C),124.65 (CH), 125.12 (CH), 126.67 (CH), 127.33 (2CH), 130.01 (CH),132.31 (2CH) 132.86 (C), 134.86 (CH), 137.37 (C), 138.69 (C), 141.28(C); HRMS (MALDI-TOF) Calcd for (C17H10BrNS): [M]+: 338.9717.Found: 338.9711.

3541-37-5 Benzo[b]thiophene-2-carboxaldehyde 736500, abenzothiophene compound, is more and more widely used in various.

Reference£º
Article; Hafedh, Nesrine; Aloui, Faouzi; Raouafi, Sondes; Journal of Molecular Structure; vol. 1165; (2018); p. 126 – 131;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

6314-28-9, Benzo[b]thiophene-2-carboxylic acid is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

REFERENCE EXAMPLE 1971-[(2-Benzothienylcarbonyl)amino]cyclohexanecarboxylic acid phenylmethyl ester Under ice-cooling, 5.9 g (31 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was added to a solution of 5 g (28 mmol) of 2-benzothiophenecarboxylic acid, 6.5 g (28 mmol) of 1-aminocyclohexanecarboxylic acid phenylmethyl ester and 4.5 g (29 mmol) of 1-hydroxybenzotriazole in methylene chloride. After the mixture was stirred at room temperature overnight, the reaction solvent was distilled off under reduced pressure. Water was added to the residue, and the mixture was extracted with ethyl acetate twice. The obtained organic layer was washed with a 10% aqueous potassium hydrogensulfate solution, a saturated aqueous sodium hydrogencarbonate solution and then saturated brine, and it was dried with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, diethyl ether was added to the obtained residue, and the mixture was stirred overnight. The crystal was collected by filtration and heated/dried under reduced pressure to obtain 10 g (91%) of the title compound.1H-NMR (CDCl3, delta): 1.25-1.78 (6H, m), 1.93-2.05 (2H, m) 2.12-2.25 (2H, m), 5.18 (2H, s), 6.24 (1H, s), 7.20-7.38 (5H, m), 7.38-7.51 (2H, m), 7.77 (1H, s), 7.80-7.91 (2H, m)

6314-28-9 Benzo[b]thiophene-2-carboxylic acid 95864, abenzothiophene compound, is more and more widely used in various.

Reference£º
Patent; SEIKAGAKU CORPORATION; US2009/137799; (2009); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem