Category: benzothiophene

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.10133-22-9,5-(Bromomethyl)benzo[b]thiophene,as a common compound, the synthetic route is as follows.

Add potassium carbonate (0.619 g, 4.4 mmol, 1.6 eq) followed by 5-bromomethyl- benzo [b] thiophene (17.7 g, 78 mmol, 1 eq) in one portion to a stirred solution of 1,1- dimethylethyl 4- [ (2-methylpropyl) amino] piperidine-1-carboxylate (20 g, 78 mmol, 1 eq) in acetonitrile (400 ml). Cool, add water (250 ml) then filter. Wash the solid with ice cold acetonitrile and leave to dry on sinter for 1 hr. Purify on a 330 g Redisep column (20 g per column) using a gradient of 0-40% Ethyl acetate/iso-hexane to give 1,1- dimethylethyl 4- { [ (l-benzothienyl-5-yl] methyl]- (2-methylpropyl) amino}-piperidine-1- carboxylate (7.64 g, 46 %) as yellow solid. LCMS Rt= 3.38 (6 min gradient) M++1 : 403.5. 1H NMR (300 MHz, CDC13) 6 ppm 7.80-7. 60 (2 H, m), 7.37-7. 33 (1 H, m), 7.32- 7.26 (1 H, m), 7.25-7. 20 (1 H, m), 4.17-3. 94 (2 H, m), 3.65 (2 H, s), 2.65-2. 36 (3 H, m), 2.24-2. 10 (2 H, d), 1.71-1. 28 (5 H, m), 1.38 (9 H, s), 0.88-0. 69 (6 H, d).

10133-22-9, As the paragraph descriping shows that 10133-22-9 is playing an increasingly important role.

Reference£º
Patent; ELI LILLY AND COMPANY; WO2005/92885; (2005); A1;,
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20532-33-6, 5-Chlorobenzothiophene is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: To a 10 mL round-bottom flask were added Cat.III (3.2 mg, 0.005 mmol, 2 mol %), Ag2O (116 mg, 0.5 mmol, 2 equiv), benzoquinone (14 mg, 0.125 mmol, 0.5 equiv), Cs(tfa) (64 mg, 0.25 mmol, 1 equiv.), benzothiophene/benzofurans (0.25 mmol, 1 equiv), aryl MIDA boronate ( 0.375 mmol, 1.5 equiv), and 15% H2O and 2% CF3SO3H of TFA (1 mL). The reaction mixture was stirred at 30-50 C for 20 h. The suspension was cooled to room temperature and extracted with dichloromethane (3 ¡Á 10 mL). The combined organic layers were washed with 20% aqueous NaHCO3 solution (40 mL). After evaporation of the solvent the crude product was purified by chromatography on silica gel to give the desired product., 20532-33-6

As the paragraph descriping shows that 20532-33-6 is playing an increasingly important role.

Reference£º
Article; Wang, Zhiwei; Li, Yabo; Yan, Beiqi; Huang, Mengmeng; Wu, Yangjie; Synlett; vol. 26; 4; (2015); p. 531 – 536;,
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20699-85-8, Methyl 5-aminobenzo[b]thiophene-2-carboxylate is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a mixture of compound 4 (100 mg, 0.237 mmol) and compound 78 (132 mg, 0.355 mmol) indichloromethane (2.3 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (71.6 mg,0.355 mmol) and 4-dimethylaminopyridine (14.45 mg, 0.118 mmol) at room temperature. Afterstirring for 2 h, the mixture was extracted with dichloromethane and water. The organic layer wasdried over magnesium sulfate, filtered, and concentrated. The crude material was purified by silicagel chromatography (dichloromethane/methanol), followed by RP-HPLC (C18 Kromasil,acetonitrile/water) to yield compound 18 (50 mg, 33% yield)., 20699-85-8

The synthetic route of 20699-85-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Reid, Emily E.; Archer, Katie E.; Shizuka, Manami; McShea, Molly A.; Maloney, Erin K.; Ab, Olga; Lanieri, Leanne; Wilhelm, Alan; Ponte, Jose F.; Yoder, Nicholas C.; Chari, Ravi V.J.; Miller, Michael L.; Bioorganic and Medicinal Chemistry Letters; vol. 29; 17; (2019); p. 2455 – 2458;,
Benzothiophene – Wikipedia
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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.,5381-20-4

General procedure: 3-Substituted propiolic acid (0.5 mmol) was dissolved in methanol (2 mL) followed by addition of appropriate 2-bromophenethylamine (0.5 mmol), aldehyde (0.5 mmol) and isocyanide (0.5 mmol). The reaction mixture was stirred at rt for 24 h in a sealed screw cap vial. The resulting mixture was concentrated and subjected to the column chromatography on silicagel with hepthane-EtOAc (15-40%) as eluent to give the desired propargylamides 7a-g,i.

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

Reference£º
Article; Peshkov, Anatoly A.; Peshkov, Vsevolod A.; Pereshivko, Olga P.; Van Der Eycken, Erik V.; Tetrahedron; vol. 71; 23; (2015); p. 3863 – 3871;,
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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

General procedure: A mixture of compound 10 (135 mg, 0.49 mmol) and 4-(thiophen-3-yl)benzoic acid (99.4 mg, 0.49 mmol) in dichloromethane (10 mL) was stirred at 0 C (ice-water bath). Dicyclohexylcarbodiimide(DCC) (121 mg, 0.59 mmol) and hydroxybenzotriazole(HOBt) (80 mg, 0.59 mmol) were added to the above solution.The ice bath was removed, and the reaction mixture was stirred at ambient temperature for 15 h. Dichloromethane (20 mL) was added into the reaction mixture, and the solution was washed with saturated aqueous NaHCO3 solution (3*10 mL). The organic layer was dried over Na2SO4, concentrated under reduced pressure, and the crude product was purified by silica gel column chromatography using dichloromethane-methanol (20:1) as the mobile phase to give 11a as a white solid (194 mg, 86%). TLC Rf 0.20 (dichloromethane-methanol 20:1); mp 125.5-126.6 C. 1H NMR(300 MHz, CDCl3) delta 7.75 (d, J = 8.7 Hz, 2H), 7.54 (d, J = 8.7 Hz, 2H),7.43 (s, 1H), 7.33 (s, 2H), 7.19 (s, 1H), 6.81-6.94 (m, 4H), 3.85 (s,3H), 3.44 (q, J = 5.1 Hz, 2H), 3.25-3.20 (m, 4H), 2.83-2.76 (m,4H), 2.57 (t, J = 5.2 Hz, 2H), 1.93 (t, J = 4.2 Hz, 2H), 1.61-1.69 (m,4H). 13C NMR (CDCl3, 300 MHz): 167.4, 151.4, 142.1, 141.2,138.8, 133.4, 127.5, 126.6, 126.3, 126.1, 121.3, 121.0, 120.7,117.9, 111.6, 57.1, 56.1, 55.3, 54.3, 52.5, 51.8, 39.4, 27.7, 27.3,25.5. HRMS (ESI) Calcd for C27H33N3O2S (M+H)+: 464.2372. Found:464.2379. Anal. (C27H33N3O2S 1.5H2C2O4) C, H, N., 6314-28-9

As the paragraph descriping shows that 6314-28-9 is playing an increasingly important role.

Reference£º
Article; Li, Aixiao; Mishra, Yogesh; Malik, Maninder; Wang, Qi; Li, Shihong; Taylor, Michelle; Reichert, David E.; Luedtke, Robert R.; MacH, Robert H.; Bioorganic and Medicinal Chemistry; vol. 21; 11; (2013); p. 2988 – 2998;,
Benzothiophene – Wikipedia
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.4521-30-6,Benzo[b]thiophen-2-amine,as a common compound, the synthetic route is as follows.,4521-30-6

Part B. 2-[4-(2-Aminoethyl)phenyl]-6-benzyloxybenzo[b]thiophen-3-yl 3-Methoxy-4-[(1-pyrrolidinyl)methyl]phenyl Ketone. 4-(2-Aminoethyl)bromobenzene (1.7 g; 8.4 mmol) and 2.3 mL (2 eq) of Et3N were combined with 3 mL of anhydrous DMF in a flame-dried, argon-filled flask. 1,2-Bis(chlorodimethylsilyl)ethane was added in 3.0 mL of DMF. The mixture was stirred at room temperature for 2 h. The mixture was filtered through a sintered glass funnel, and concentrated under reduced pressure. The colorless oil subsequently crystallized. The protected bromobenzene derivative was converted to the corresponding Grignard reagent. Magnesium (33 mg; 1.35 mmol) was placed in a flask which was subsequently flame-dried and filled with argon. Anhydrous THF (3 mL) and the protected aminoarylbromide were added with a small crystal of I2. The mixture was heated under reflux for 3 h. The resulting reagent was used without purification. The above aminobenzothiophene (Part A) (4.10 g; 8.2 mmol) was dissolved in anhydrous THF in a flame-dried, argon-filled flask, and cooled in an ice-water bath. The Grignard reagent prepared above (1.5 eq) was added dropwise.

The synthetic route of 4521-30-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Eli Lilly and Company; US6391901; (2002); B1;,
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104795-85-9, Methyl 6-chlorobenzo[b]thiophene-2-carboxylate is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

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].

104795-85-9, As the paragraph descriping shows that 104795-85-9 is playing an increasingly important role.

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;,
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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,4923-87-9

Step A: 5-Bromo- 1 -benzothiophene 1 J -dioxide5-Bromo- 1 -benzothiophene (1.50 g, 7.04 mmol) was dissolved in chloroform (47 mL) and allowed to stir vigorously at ambient temperature. m-CPBA (4.34 g, 17.6 mmol) was added in three portions and the resulting mixture was maintained at ambient temperature for 16 hours. The mixture was then diluted with 1M aqueous sodium thiosulfate and extracted with EtOAc. The organic layer was again washed with 1M aqueous sodium thiosulfate, saturated aqueous NaHC03, brine, dried over anhydrous MgS04, filtered, and concentrated in vacuo. The residue was purified by MPLC on silica gel (using a gradient elution of 0-30% EtOAc/hexanes). Desired fractions were identified, combined, and concentrated in vacuo to afford the title compound. 1H NMR (600 MHz, CDC13): delta 7.65 (dd, J= 7.9, 1.8 Hz, 1H), 7.55 (d, J= 7.9 Hz, 1H), 7.50 (d, J= 1.8 Hz, 1H), 7.15 (d, J= 6.9 Hz, 1H), 6.74 (d, J= 6.9 Hz, 1H).

As the paragraph descriping shows that 4923-87-9 is playing an increasingly important role.

Reference£º
Patent; MERCK SHARP & DOHME CORP.; BRUBAKER, Jason; DINSMORE, Christopher J.; HOFFMAN, Dawn Marie; JUNG, Joon; LIU, Duan; PETERSON, Scott; SIU, Tony; TORRES, Luis E.; ZHANG, Hongjun; WEI, Zhongyong; SHI, Feng; WO2013/40863; (2013); A1;,
Benzothiophene – Wikipedia
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95-15-8,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.95-15-8,Thianaphthene,as a common compound, the synthetic route is as follows.

EXAMPLE 35 1-[3-Acetylthio-3-(benzo[b]thien-2-ylcarbonyl)-2-methylpropionyl]-L-proline To a solution of 2.68 g. (0.020 mole) of benzo[b]-thiophene in 40 ml. of ether cooled at -20 C. is added 0.020 moles of n-butyl lithium (2.54 N solution in hexane). The mixture is stirred at -20 C. for 15 minutes, then is allowed to warm to room temperature. Then 2.70 g. (0.020 mole) of N-methylformamilide is added and the mixture is stirred for 24 hours. The reaction is quenched with water and the mixture is treated with saturated sodium bisulfite solution. The bisulfite addition product is collected by filtration. The wet cake is slurried in water and decomposed by the addition of solid sodium carbonate. The mixture is filtered and the solid is washed with water and dried to give 1.75 g. of benzo[b]thiophene-2-carboxaldehyde.

The synthetic route of 95-15-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; American Cyanamid Company; US4299769; (1981); A;,
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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,130-03-0

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.

As the paragraph descriping shows that 130-03-0 is playing an increasingly important role.

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