Category: benzothiophene

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

To a 20-mL sealed tube purged and maintained with an inert atmosphere of nitrogen,was placed a solution of 2-ethyl-5-[(3-methylcyclohexyl)oxyjaniline (1.0 g,4.29 mmol,as prepared in the previous step) in EtOH (10 mL) then 2-oxopropanoic acid (1.13 g,12.83 mmol) and 1-benzothiophene-3-carbaldehyde (626 mg,3.86 mmol) were added. The reaction was stirred overnight at 120C then concentrated under reduced pressure. The crude product was purified by Flash-PrepHPLC (IntelFlash-1: Column,C18; mobile phase,ACN,water (0.5% TFA) and ACN (80.0%ACN up to 95.0% in 15 mm); Detector,UV 254 nm) then the isomers were separated by PrepSFC (Prep 5FC350-2: Column,CHIRALPAK AD-H SFC,5*25cm,Sum; mobile phase,C02(50%),ethanol(2mM NH3-MeOH); Detector,UV 254 nm) affording 56.7 mg (3%) of 2-(1-benzothiophen-3-yl)-8-ethyl-5-[[(1 R,3 S)-3-methylcyclohexylj oxyl quinoline-4-carboxylic acid (Compound 182) as alight yellow solid,53.9 mg(4%) of 2-(1-benzothiophen-3-yl)-8-ethyl-5-[[(1 R,3R)-3-methylcyclohexyll oxyl quinoline-4-carboxylic acid (Compound 184) as a light yellow solid and a mixture of Compound 181 and Compound 183. This mixture was separated by Chiral-Prep-HPLC (HPLC-09: Column: CHIRALPAK-AD-H-5L002,20*250 mm; Mobile Phase A:Hex–HPLC,Mobile Phase B: IPA–HPLC; Flow rate: 15 mL/min; Gradient: 40 B to 40 B in 16 mm; 254 nm) affording 55.7 mg (3%) of 2-(1-benzothiophen-3-yl)-8-ethyl-5-[[(1 S,3R)-3-methylcyclohexyll oxyl quinoline-4-carboxylic acid (Compound 181) as a brown solid and 56.8 mg (3%) of 2-(1-benzothiophen-3-yl)-8-ethyl-5-[[(1 S,35)-3-methylcyclohexyljoxyjquinoline-4-carboxylic acid (Compound 183) as a brown solid. j0401j 2-(1-Benzothiophen-3-yl)-8-ethyl-5-j j(1S,3R)-3-methylcyclohexyljoxyjquinoline-4-carboxylic acid (Compound 181): Mass Spectrum(LCMS,ESI pos): Calcd. for C27H28NO3S: 446.2 (M+H); Found: 446.2. 1H NMR (300 MHz,DMSO-d6): oe 13.14 (brs,1H ),9.26 (d,J= 7.5 Hz,1H ),8.81 (s,1H ),8.12 (d,J= 7.8 Hz,1H ),8.04 (s,1H ),7.46-7.61 (m,3H),7.02 (d,J= 8.1H z,1H ),4.86-4.85 (m,1H ),3.25 (q,J= 7.5Hz,2H),1.97-1.72 (m,4H),1.70-1.61 (m,1H ),1.60-1.45 (m,2H),1.37 (t,J= 7.5 Hz,3H),1.10-0.93 (m,1H ),0.87 (d,J= 6.3 Hz,1H ). HPLC purity (254 nm): 99.5%.j0402j 2-(Benzo jbjthiophen-3-yl)-8-ethyl-5-(((1R,3S)-3-methylcyclohexyl)oxy)quinoline-4-carboxylic acid (Compound 182): Mass Spectrum(LCMS,ESI pos): Calcd. for C27H28NO3S: 446.2 (M+H); Found: 446.2. 1H NMR (300 MHz,DMSO-d6): oe 13.14 (brs,1H ),9.26 (d,J= 7.5 Hz,1H ),8.81 (s,1H ),8.12 (d,J= 7.8 Hz,1H ),8.04 (s,1H ),7.46-7.61 (m,3H),7.02 (d,J= 8.1H z,1H ),4.86-4.85 (m,1H ),3.25 (q,J= 7.5Hz,2H),1.97-1.72 (m,4H),1.70-1.61 (m,1H ),1.60-1.45 (m,2H),1.37 (t,J 7.5 Hz,3H),1.10-0.93 (m,1H ),0.87 (d,J= 6.3 Hz,1H ). HPLC purity (254 nm): 99.7%.j0403j 2-(Benzo jbjthiophen-3-yl)-8-ethyl-5-(((1S,3S)-3-methylcyclohexyl)oxy)quinoline-4-carboxylic acid (Compound 183): Mass Spectrum(LCMS,ESI pos): Calcd. for C27H28NO3S: 446.2 (M+H); Found: 446.2. 1H NMR (300 MHz,DMSO-d6): oe 13.14 (s,1H ),9.27 (d,J= 7.8 Hz,1H ),8.81 (s,1H ),8.12 (d,J 7.8 Hz,1H ),8.04 (s,1H ),7.46-7.61 (m,3H),7.11 (d,J= 8.1H z,1H ),4.50-4.57 (m,1H ),3.24 (q,J= 7.5Hz,2H),2.10-2.13 (m,2H),1.47-1.80 (m,3H),1.29-1.43 (m,5H),1.10-1.28 (m,1H ),0.94 (d,J= 6.6 Hz,3H),0.79-0.89 (m,1H ). HPLC purity (254 nm): 99.6%.j0404j 2-(Benzo jbjthiophen-3-yl)-8-ethyl-5-(((1R,3R)-3-methylcyclohexyl)oxy)quinoline-4-carboxylic acid (Compound 184): Mass Spectrum(LCMS,ESI pos): Calcd. for C27H28NO3S: 446.2 (M+H); Found: 446.2. 1H NMR (300 MHz,DMSO-d6): oe 13.14 (s,1H ),9.27 (d,J= 7.8 Hz,1H ),8.81 (s,1H ),8.12 (d,J 7.8 Hz,1H ),8.04 (s,1H ),7.46-7.61 (m,3H),7.11 (d,J= 8.1H z,1H ),4.50-4.57 (m,1H ),3.24 (q,J= 7.5Hz,2H),2.10-2.13 (m,2H),1.47-1.80 (m,3H),1.29-1.43 (m,5H),1.10-1.28 (m,1H ),0.94 (d,J= 6.6 Hz,3H),0.79-0.89 (m,1H ). HPLC purity (254 nm): 99.7%.

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

Reference£º
Patent; PROTEOSTASIS THERAPEUTICS, INC.; MUNOZ, Benito; BASTOS, Cecilia, M.; PARKS, Daniel; KOMBO, David; (301 pag.)WO2017/62581; (2017); A1;,
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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

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., 130-03-0

130-03-0 Benzo[b]thiophen-3(2H)-one 10986413, abenzothiophene compound, is more and more widely used in various.

Reference£º
Article; Zweig, Joshua E.; Ko, Tongil A.; Huang, Junrou; Newhouse, Timothy R.; Tetrahedron; vol. 75; 34; (2019);,
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351005-12-4, 5-Bromo-1,3-dihydrobenzo[c]thiophene 2,2-dioxide is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,351005-12-4

5-bromo-1 ,3-dihydro-2-benzothiophene-2,2-dione (475 mg, 1.92 mmol)and freshly prepared bromo[1-(methoxycarbonyl)cyclopropyl]zinc (4.81 mL, 3.84mmol) were dissolved in dry THF (5 mL) and the solution was degassed by nitrogen bubbling for 5 mm. Then, XPhos (183 mg, 0.38 mmol) and Pd2(dba)3 (176 mg, 0.19 mmol) were incorporated and the reaction mixture was stirred at75C for lh. The mixture was cooled to rt and quenched with water and extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered and the solution was concentrated to dryness. The crude was adsorbed onto silica gel and purified by column chromatography eluting with a gradient of Cyclohexane/EtOAc from [90:10] to [60:40]. The product fractions were combined and concentrated to dryness to afford a white solid. The solid was triturated with cyclochexane and dried under vacuum at 40C to constant weight to afford methyl 1 -(2,2-dioxo-1 ,3-d ihyd ro-2-benzoth iophen-5-yl)cyclopropane-1 – carboxylate Ex.43a (254 mg, 50%) as white solid. 1 H NMR (300 MHz, DMSOd6, din ppm): 1.18-1.22 (m, 2H), 1.47-1.51 (m, 2H), 3.54 (s, 3H), 4.46 (s, 4H),7.29-7.35 (m, 3H).

351005-12-4 5-Bromo-1,3-dihydrobenzo[c]thiophene 2,2-dioxide 288396, abenzothiophene compound, is more and more widely used in various.

Reference£º
Patent; GENFIT; DELHOMEL, Jean-Francois; PERSPICACE, Enrico; MAJD, Zouher; PARROCHE, Peggy; WALCZAK, Robert; (284 pag.)WO2018/138362; (2018); A1;,
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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,6314-28-9

Benzo[b]thiophene-2-carboxylic Acid [4a-(3-Methoxyphenyl)-8a-methyl-2-(3-phenylpropyl)octahydroisoquinolin-6-yl]amide (25d).; To compound 24 (52 mg, 0.132 mmol) dissolved in anhydrous THF (10 mL) was added benzo[b]thiophene-2-carboxylic acid (35 mg, 0.198 mmol), triethylamine (0.092 mL, 0.662 mmol), and BOP reagent (64 mg, 0.145 mmol), and the reaction mixture was allowed to stir at room temperature for 1.5 h. Reaction was monitored by TLC (30% CMA 80 in CH2Cl2). The reaction mixture was diluted with EtOAc (20 mL) and washed with saturated aqueous NaHCO3 (20 mL) followed by water (20 mL). The aqueous layers were back extracted with EtOAc (2¡Á20 mL). The combined organic layers were washed with 1 N NaOH (25 mL), dried (MgSO4), and concentrated under reduced pressure to afford crude product. The crude product was purified by flash chromatography (20% CMA 80 in CH2Cl2) to afford 70 mg (96%): LCMS (ESI): m/z 553.9 (M+H)+; 1H NMR (CDCl3, 300 MHz) delta 7.74-7.81 [m, 3H], 7.36-7.40 [m, 2H], 7.18-7.31 [m, 7H], 6.74-6.75 [m, 1H], 6.12 [d, J=9 Hz, 1H], 4.47 [m, 1H], 3.81 [s, 3H], 2.76-2.79 [br, 1H], 2.59-2.67 [m, 3H], 2.36-2.39, [m, 2H], 2.15-2.29 [m, 4H], 1.89-1.94 [m, 3H], 1.60-1.81 [m, 4H], 1.53 [d, J=12 Hz, 1H], 1.26-1.32 [m 1H], 1.24 [s, 3H]; 13C NMR (CDCl3, 300 MHz) delta 161.9, 159.3, 148.7, 142.8, 141.2, 139.5, 139.2, 128.9, 128.8, 128.7, 126.6, 126.1, 125.3, 125.2, 123.1, 122.0, 116.4, 110.8, 62.3, 58.3, 55.6, 51.2, 47.1, 44.4, 38.1, 37.0, 36.8, 35.6, 34.0, 29.2, 28.3, 26.7.

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

Reference£º
Patent; Research Triangle Institute; US2007/27182; (2007); A1;,
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95-15-8, Thianaphthene is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

95-15-8, General procedure: In 0.5 M hexane solvent, 1.25 molar equivalents of Na-TMP was reacted with 0.4 mmol of benzo[b]thiophene (arene) at 25 C. for 30 minutes, 1.5 molar equivalents of heavy water (D2O: electrophilic reagent) was then added thereto and reacted therewith at 0 C. for 1 hour. The product was evaluated through analysis by 1H-NMR, and the yield of isolated deuterated benzo[b]thiophene in which a hydrogen atom located at 2-position of benzo[b]thiophene was substituted by heavy hydrogen was calculated in the same manner as in Experiment Number 1. The isolated yield was 99%.A reaction was performed using benzo[b]thiophene as an arene and iodomethane (MeI) as an electrophilic reagent in the same manner as in Experiment Number 2, the product was then evaluated, and the yield of isolated 2-methyl-benzo[b]thiophene in which a methyl group (-Me) was added at 2-position of benzo[b]thiophene was calculated. The isolated yield was 77%

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

Reference£º
Patent; KOBELCO ECO-SOLUTIONS CO.,LTD.; MURAKAMI, Yoshiaki; FUKUSHIMA, Miyuki; TAKAI, Kazuhiko; ASAKO, Sobi; (16 pag.)US2019/359571; (2019); A1;,
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