Heterocyclic Building Blocks-Benzothiophene

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.

A solution of 6.58 ML (47 MMol) diisopropylamine in 25 ML tetrahydrofuran was cooled to 0C and then 29.4 ML (47 MMol) n-butyllithium (1.6 M in hexanes) were added.. The mixture was allowed to warm to room temperature over 1 hour and was then added dropwise to a mixture of 5.0 gm (24 MMol) 7-bromobenzothiophene and 6.1 ML (47 MMol) trimethylsilyl chloride in 15 ML tetrahydrofuran at -78C. The reaction mixture was stirred for 2 hours and was then poured into ice water.. This mixture was extracted well with diethyl ether.. The combined organic phases were washed with 1N hydrochloric acid, dried over sodium sulfate and concentrated under reduced pressure to provide 6.1 gm (91%) of the title compound., 1423-61-6

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

Reference£º
Patent; ELI LILLY AND COMPANY; EP1204660; (2004); B1;,
Benzothiophene – Wikipedia
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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

5381-20-4, General procedure: Titanium tetrachloride (1.90 g, 10 mmol) was slowly added to100 mL of anhydrous THF at 0 C, followed by addition of 5 mmol of the aldehyde (1) and stirred for 10 min, then ethyl 2-(3-bromopyridin-2-yl)acetate (2) (1.47 g, 6 mmol) was added. Subsequently, a solution of pyridine (3.16 g, 40 mmol) in 25 mL of anhydrous THF was added dropwise during a period of 30-60 min at 0 C. The reaction mixture was then stirred for 1 h at room temperature and refluxed for 24 h. After that the mixture was poured on to crashed ice and extracted with ethyl acetate (4 30 mL). The combined extracts were successively washed with brine, saturated sodium hydrogen carbonate and brine, and then dried over anhydrous MgSO4. The organic phase was filtrated and the solvent was removed in vacuo, the residue was purified by column chromatography (silica gel) using PE/EA (5:1) / DCM/MeOH (50:1) to provide 3.

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

Reference£º
Article; Li, Bo; Yue, Zhi-Zhou; Feng, Jian-Ming; He, Qian; Miao, Ze-Hong; Yang, Chun-Hao; European Journal of Medicinal Chemistry; vol. 66; (2013); p. 531 – 539;,
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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 (0.106 g, 0.65 mmol), methyl 3-cyclopropyl-3-oxopropanoate (0.071 g, 0.72 mmol) and 4-amino-3-penten-2-one (0.088 g, 0.61 mmol) and acetic acid (0.035 mL) in isopropylalcohol (1.5 mL) was heated to 100C and left to stir for 19 hours. The mixture was allowed to cool to RT and was then treated with saturated aqueous sodium bicarbonate solution (10 mL). The solid was filtered off, washed with water, dried and purified by column chromatography (4:1 hexane: ethyl acetate) affording a fine yellow solid (0.075 g, 44 %). 1H-NMR (400 MHz, DMSO-d6) delta = 0.76 (s, 2H), 0.96 (d, 2H), 2.12 (s, 3H), 2.33 (s, 3H), 2.69 (s, 1H), 3.58 (s, 3H), 5.43 (s, 1H), 7.15 (s, 1H), 7.31 (s, 1H), 7.38 (s, 1H), 7.90 (s, 2H), 8.05 (d, 1H). HPLC-MS: Rt 4.302 min, m/z 234.1 (MH+-133). (0600) A second reaction product was isolated by column chromatography: Example J1-a: Dimethyl 4-(benzo[b]thiophen-3-yl)-2,6-dicyclopropyl-1,4-dihydropyridine-3,5-dicarboxylate (0601) 1H-NMR (400 MHz, DMSO-d6) delta = 0.56 (s, 2H), 0.82 (s, 2H), 0.90 (d, 2H), 1.04 (s, 2H), 2.56 (m, 2H), 3.55 (s, 5H), 5.37 (s, 1 H), 7.05 (s, 1 H), 7.11 (s 1 H), 7.32 (t, 1 H), 7.39 (t, 1H), 7.90 (d, 1 H), 7.98 (s, 1 H). HPLC-MS: Rt 4.935; m/z 276.1 (MH+)., 5381-20-4

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

Reference£º
Patent; Oncostellae, S.L.; KURZ, Guido; CAMACHO GOMEZ, Juan; (123 pag.)EP3480201; (2019); A1;,
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Benzothiophene | C8H6S – PubChem

6314-28-9,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.6314-28-9,Benzo[b]thiophene-2-carboxylic acid,as a common compound, the synthetic route is as follows.

benzo[b]thiophene-2-carboxylic acid ( 159 mg , 0.892 mmol ) ,2-amino-biphenyl (156 mg, 0.922 mmol), DCC (393 mg, 1.90mmol) and DMAP ( 26 mg , 0.21 mmol) dissolved in dichloromethane (20 mL) and stirred for 14 hours at room temperature .When confirmation thin layer chromatography (TLC), when a new spot is generated , and then adding water to the reaction mixture , dichloromethane coming And extracted twice with . The extracted organic layer was dried over magnesium sulfate and concentrated under reduced pressure. It was purified by column chromatography (silica gel , ethyl acetate / n- hexane = 1/9 ) to obtain the object compound ( 102 mg , 35 % ) as a white solid

The synthetic route of 6314-28-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Korea Research Instituteof Chemical Technology; Jong, Yeong Sik; Kim, Pil Ho; Han, Soo Bong; Achari, Ragavendra; Kim, Mi Hyeon; Lee, Jong Kyo; Shin, Jin Soo; (128 pag.)KR2015/134301; (2015); A;,
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154650-81-4, Benzo[b]thiophene-6-carbonitrile is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: Substituted benzothiophene (1 eq.) was dissolved in 1,2-dichloroethane. A solution of bromine(1.12 eq.) in 1,2-dichloroethane (CH2Cl2 for 17) was slowly added to the reaction mixture at 0 C, thenwarmed to r.t., and stirred for 2 h. Reaction progress was monitored by thin-layer chromatography(TLC, reverse phase silica gel, MeOH). Aqueous Na2S2O3 solution was added, and the desired productwas extracted with CH2Cl2. Combined organic layers were washed with brine, and dried overanhydrous Na2SO4. After filtration, the solvent was removed under reduced pressure. The productwas purified using column chromatography. [34]

154650-81-4, 154650-81-4 Benzo[b]thiophene-6-carbonitrile 21816574, abenzothiophene compound, is more and more widely used in various.

Reference£º
Article; Konstantinovi?, Jelena; Videnovi?, Milica; Srbljanovi?, Jelena; Djurkovi?-Djakovi?, Olgica; Bogojevi?, Katarina; Sciotti, Richard; ?olaja, Bogdan; Molecules; vol. 22; 3; (2017);,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.310466-38-7,4-Fluorobenzo[b]thiophene,as a common compound, the synthetic route is as follows.

General procedure: A solution of 2,6-difluorobenzaldehyde 7 (1.0g, 7.0mmol) and potassium carbonate (1.45g, 10.5mmol) in DMF (25mL) at 0C was added slowly with methyl thioglycolate (0.7mL, 7.7mmol) and the mixture was stirred at the same temperature for 30min. The reaction mixture was stirred at room temperature for 14h and then at 60C for 6h. Solvent was removed and the resulting residue was diluted with ethyl acetate (60mL) followed by washed with water (20mL). The organic layer was dried over Na2SO4, filtered, and concentrated to obtain a crude compound. The above crude compound (500mg, 2.38mmol) and potassium hydroxide (400mg, 7.14mmol) were taken into a mixture of EtOH/ water (12/2mL) and heated to reflux for 2h. The reaction mixture was cooled to room temperature and concentrated. The resulting residue was diluted with water (20mL), acidified with 6N HCl and extracted with ethyl acetate (60mL). The organic layer was dried over Na2SO4, filtered, and concentrated to afford colorless crystals. The resulting colorless crystals (1.0g, 5.1mmol) were mixed together with powdered copper (97mg, 1.53mmol) in quinoline (10mL) and heated at 185C for 2h. The reaction mixture was cooled to room temperature and diluted with ethyl acetate (60mL) and 2N HCl (20mL). The mixture was filtered and washed with ethyl acetate (50mL). The organic layer was dried over Na2SO4, filtered, and concentrated. The resulting crude product was purified by column chromatography using hexane to give colorless oil. To a solution of the above compound (1.0g, 6.57mmol) in dry THF (13mL) was added a 1.6M solution of n-BuLi in hexane (4.2mL, 6.57mmol) drop wise at-78C. The reaction mixture was stirred at same temperature for 30min and was added tri-n-butyltin chloride (1.79mL, 6.57mmol). The resulting solution was stirred for 1h at-78C and then at room temperature for another 1h. The reaction mixture was concentrated under reduced pressure and the resulting residue was diluted with ethyl acetate (60mL), washed with aqueous KF (2¡Á20mL) and with water (2¡Á20mL). The combined organic layers ware dried over MgSO4 and concentrated to obtain a crude product. A solution of the above crude compound (1.0g, 2.27mmol) and 2-bromopyridine (360mg, 2.27mmol) in toluene (22mL) was added with Pd(PPh3)4 (131mg, 0.114mmol). The reaction mixture was degassed thoroughly with nitrogen and stirred at 110C for 8h. After cooling to room temperature, the mixture was concentrated under reduced pressure. The obtained crude product was diluted with ethyl acetate, filtered through Celite, and washed with aqueous KF (2¡Á15mL) followed by brine (15mL) and water (15mL). The organic layer was dried over MgSO4, filtered, and concentrated to afford a crude product which was purified by column chromatography using ethyl acetate/hexane (1:9) to afford the pure compound 8 as a white solid (260mg 40%).

310466-38-7, The synthetic route of 310466-38-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Li, Chung-Yen; Su, Chaochin; Wang, Hsiou-Hsuan; Kumaresan, Prabakaran; Hsu, Chia-Hsuan; Lee, I-Ting; Chang, Wei-Chun; Tingare, Yogesh S.; Li, Ting-Yu; Lin, Chia-Feng; Li, Wen-Ren; Dyes and Pigments; vol. 100; 1; (2014); p. 57 – 65;,
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.

Example 4: Synthesis o -(benzothiophen-2-yl)-2-hydroxyethylsulfamide[0097] 2-Amino-l-benzo[b]thiophen-2-yl-ethanol hydrochloride salt. To a stirring solution of benzo[b]thiophene-2-carbaldehyde (1.0 g, 6.16 mmol) and trimethylsilyl cyanide (0.92 mL, 6.78 mmol) in dichloromethane (8 mL) at room temperature under nitrogen was added a few crystals of zinc iodide. The mixture was stirred at this temperature for 20 hours and concentrated. The residue was dissolved in borane in tetrahydrofuran (1M, 13.6 mL) and heated to reflux for 5 hours. The mixture was cooled to room temperature and concentrated. The syrup was dissolved in methanol (25 mL), treated with hydrogen chloride (4M in dioxane, 6.8 mL), and heated to reflux for 2 hours, and then concentrated. The solid obtained was dissolved in hydrochloric acid (2N, 10 mL) and extracted twice with diethyl ether. The aqueous solution was concentrated, crystallized from methanol/ether, and dried in vacuum oven to give a yellow (770 mg,54%)., 3541-37-5

As the paragraph descriping shows that 3541-37-5 is playing an increasingly important role.

Reference£º
Patent; ADVANCED NEURAL DYNAMICS, INC.; FOX CHASE CHEMICAL DIVERSITY CENTER, INC.; SMITH, Garry, Robert; BRENNEMAN, Douglas, Eric; REITZ, Allen, B.; DU, Yanming; WO2011/97337; (2011); 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.20699-85-8,Methyl 5-aminobenzo[b]thiophene-2-carboxylate,as a common compound, the synthetic route is as follows.

Compound 6 (255 mg, 1.062 mmol) and compound 7 (200 mg, 0.965 mmol) were dissolved indimethylformamide (3.22 mL). 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (222 mg, 1.158mmol) was added to the reaction mixture, followed by 4-dimethylaminopyridine (118 mg, 0.965mmol) and the reaction was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate and was washed with saturated ammonium chloride, brine, dried oversodium sulfate, filtered and concentrated. The crude product was purified by silica gelchromatography (0% to 40% ethyl acetate/hexanes) to obtain compound 7 as an orange-white solid(300 mg, 0.699 mmol, 72% 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
Benzothiophene | C8H6S – PubChem

89673-36-9,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.89673-36-9,tert-Butyl benzo[b]thiophen-2-ylcarbamate,as a common compound, the synthetic route is as follows.

A solution of compound 235 (0.250 g, 1.00 mmol) was stirred in 4 M HCl solution in 1,4-dioxane (3 mL) at room temperature for 2 hrs at which time thin layer chromatography (DCM/Hexanes) indicated the reaction was complete. The reaction mixture was cooled to room temperature and concentrated under vacuum. The residue was diluted with acetonitrile, sonicated, and concentrated to afford compound 236 as a grey solid 0.24 g (91%). HPLC-MS tR=1.5 Min(UV254 nm). Mass calculated for formula C8H7NS, M+149.21, observed LC/MS m/z 150.40 (M+H).

89673-36-9 tert-Butyl benzo[b]thiophen-2-ylcarbamate 13182766, abenzothiophene compound, is more and more widely used in various.

Reference£º
Patent; Schering Corporation; US2007/105864; (2007); 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.17402-83-4,Benzo[b]thiophen-4-amine,as a common compound, the synthetic route is as follows.

(Step 1) Diisopropylethylamine (0.10 ml) was added to a solution of ethyl 5-chloro-3-(methylthio)-1,2,4-triazine-6-carboxylate (70 mg) and benzo[b]thiophen-4-amine (70 mg) in THF (1 ml), and the reaction solution was stirred at room temperature for 35 minutes. The solvent was evaporated under vacuum, and then the resultant residue was purified by column chromatography on silica gel (developing solvent: hexane/ethyl acetate) to obtain ethyl 5-(benzo[b]thiophen-4-ylamino)-3-(methylthio)-1,2,4-triazine-6-carboxylate as a white solid.

17402-83-4, The synthetic route of 17402-83-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Taiho Pharmaceutical Co., Ltd.; SAKAMOTO, Toshihiro; MITA, Takashi; SHIBATA, Kazuaki; OGINO, Yoshio; KOMATANI, Hideya; EP2762476; (2014); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem