Day: August 26, 2020

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

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

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

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

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

20532-33-6, 5-Chlorobenzothiophene is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Reference Example 32 Preparation of 5-chlorobenzo[b]thiophene-2-carboxaldehyde To a solution of 5-chlorobenzo[b]thiophene (6.14 g) in THF (120 ml) was added n-BuLi (1.6 M solution in hexane, 27.3 ml) at -78 C., and the mixture was stirred for 2 hours. To this mixture was added DMF (8.5 ml), and the mixture was stirred for 1 hour at -78 C. to -30 C. The reaction was quenched by the addition of water and allowed to warm to room temperature. The organic layer was separated, diluted with ethyl acetate, washed with 10% citric acid solution, brine, dried over MgSO4, and concentrated. The residue was titurated with diisopropylether to give the titled compound as colorless crystals (5.92 g). 1H-NMR (CDCl3) delta: 7.48 (1dd, J=8.8, 2.0 Hz), 7.84 (1H, d, J=8.8 Hz), 7.94 (1H, d, J=2.0 Hz), 7.97 (1H, s), 10.12 (1H, s). IR (KBr): 1678, 1516, 1140 cm-1.

20532-33-6 5-Chlorobenzothiophene 11309754, abenzothiophene compound, is more and more widely used in various.

Reference£º
Patent; Takeda Chemical Industries, Ltd.; US6420375; (2002); B1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

34761-09-6, Ethyl 3-aminobenzo[b]thiophene-2-carboxylate is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 1I (R)-3-[2-[3-(2-Methoxyphenyl)-1-pyrrolidinyl]ethyl]-[1]benzothieno[3,2-d]pyrimidine-2,4(1H,3H)-dione Monohydrochloride A solution of Example 1H (664 mg, 3 mmol) and triethylamine (0.84 mL, 6 mmol) in THF (20 mL) was treated with 1.93M phosgene in toluene (1.7 mL, 3.3 mmol), stirred for 2 hours, treated with a solution of Example 1G (330 mg, 1.5 mmol) in toluene (50 mL), stirred for 4 hours, treated with 5% aqueous sodium bicarbonate and extracted with methylene chloride. The extract was dried (Na2 SO4) and concentrated, and the residue was dissolved in toluene, refluxed for 18 hours, cooled and filtered. The filtrate was treated with ethanol saturated with HCl, triturated with diethyl ether and filtered to provide the title compound. mp 169-173 C.; [alpha]D23 =+3.7 (c 0.004, MeOH); 1 H NMR (300 MHz, CD3 OD) delta 2.19-2.55 (m, 2H), 3.30 (m, 1H), 3.55 (m, 1H), 3.67 (t, 3H), 3.78 (m, 1H), 3.90 (s, 3H), 4.00 (m, 1H), 4.16 (q, 1H), 4.48 (t, 2H), 6.98 (m, 2H), 7.28 (m, 2H), 7.60 (m, 2H), 8.01 (d, 1H), 8.21 (d, 1H); MS (DCI/NH3) m/e 422 (M+H)+; Anal. calc’d for C23 H23 N3 O3 S.1.0 HCl: C, 60.32, H, 5.28, N, 9.18,. Found: C, 60.82, H, 5.36, N, 9.22.

As the paragraph descriping shows that 34761-09-6 is playing an increasingly important role.

Reference£º
Patent; Abbott Laboratories; US6133275; (2000); A;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

130-03-0, Benzo[b]thiophen-3(2H)-one is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a 5 mL flame-dried microwave flask was added benzo[b]thiophen-3(2H)-one (0.24 mmol, 0.12 equiv) and 5-aryl-2-formylpyrrole (0.2 mmol, 0.1 equiv). The flask was capped with analuminume-PTFE crimp cap, sealed, and evacuated and backfilled with nitrogen three times. To the flask was then added anhydrous toluene (2 mL, 0.1M in aldehyde) and piperidine (10 mL, 0.1 mmol,0.5 equiv). The flask was transferred to a pre-warmed oil bath set to 111 C and stirred for 2 h. After 2 h the flask was removed from theoil bath and cooled to room temperature and then to 0 C in a water-ice bath. To the flask was added hexanes (5 mL) and the flask was allowed to sit for an addition 10-30 min. The mixture was the filtered, and the precipitate was then triturated with hexanes to until the filtrate ran clear to provide the pure product as a red, blue,or purple solid depending on the substrate.

The synthetic route of 130-03-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Zweig, Joshua E.; Ko, Tongil A.; Huang, Junrou; Newhouse, Timothy R.; Tetrahedron; vol. 75; 34; (2019);,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

1127-35-1, Benzo[b]thiophene-3(2H)-one 1,1-Dioxide is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: To a stirred solution of the sulfenyl amide peptide 1 (20 mg,0.060 mmol) in 3 mL of 3:1 methanol:HEPES buffer (HEPES,50 mM, NaCl, 100 mM, EDTA, 1 M, pH 7.0) was added the sulfone-containing nucleophile (1.1 equiv) and the mixture stirred at room temperature (24 C). When the reaction was judged completeby TLC analysis, methanol was completely removed by blowinga stream of nitrogen gas on the solution, and the resulting aqueous solution extracted with ethyl acetate or dichloromethane(2 2 mL). The combined organic layers were dried over anhydrous Na2SO4 and concentrated by rotary evaporation. The products were isolated by column chromatography on silica gel eluted with mixtures of either ethyl acetate-hexane or methanol-dichloromethane. (2’S)-Dimethyl 2,2′-(((2R,2’R)-3,3′-((1,1-dioxido-3-oxo-2,3-dihydrobenzo[b]thiophene-2,2-diyl)bis(sulfanediyl))bis(2-((tert-butoxycarbonyl)amino)propanoyl))bis(azanediyl))bis(3-methylbutanoate) (3c). Colorless oil (20 mg, 78%) Rf = 0.25 (40% ethyl acetate/hexanes). 1H NMR (CDCl3, 500 MHz) delta 8.05 (d, J = 7.5 Hz, 1H), delta 7.92-7.97 (m, 2H), delta 7.83-7.86 (m, 1H), delta 5.60 (s, 1H) delta 5.55 (d, J = 7.5 Hz, 1H), delta 4.53-4.56 (m, 4H), delta 3.76 (s, 3H), delta 3.75 (s, 3H), delta 3.16-3.31 (m, 4H), delta 2.15-2.22 (m, 2H), delta 1.45 (s, 9H), delta 1.43 (s, 9H), delta 0.92-0.95 (m, 12H); 13C NMR (CDCl3, 150 MHz) delta 183.4, 172.1, 169.8, 169.7, 155.5, 155.4, 142.0, 137.2, 134.7, 130.1, 126.5, 122.4, 80.5, 80.4, 79.2, 57.6, 57.5, 53.3, 52.4, 52.3, 34.0, 33.8, 31.2, 29.7, 28.3, 19.0, 17.9; IR (cm-1) 3408, 3354, 3058, 2969, 2933, 2872, 1716, 1680, 1504, 1363, 1262, 1212, 1158, 1021, 737, 705; HRMS (ESI-TOF, [M+H]+) m/z calculated for C36H55N4O13S3: 847.2928, found 847.2911.

1127-35-1 Benzo[b]thiophene-3(2H)-one 1,1-Dioxide 70780, abenzothiophene compound, is more and more widely used in various.

Reference£º
Article; Parsons, Zachary D.; Ruddraraju, Kasi Viswanatharaju; Santo, Nicholas; Gates, Kent S.; Bioorganic and Medicinal Chemistry; vol. 24; 12; (2016); p. 2631 – 2640;,
Benzothiophene – Wikipedia
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).

346592-74-3 7-Fluorobenzo[b]thiophene 21866059, abenzothiophene compound, is more and more widely used in various.

Reference£º
Patent; Smith-Swintosky, Virginia L.; US2007/191451; (2007); A1;; ; Patent; Smith-Swintosky, Virginia L.; US2007/191453; (2007); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem