Category: benzothiophene

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

A solution of 4-(4-(((6aS,)-5-((allyloxy)carbonyl)-2-methoxy-i2-oxo-6-((tetrahydro-2if- pyran-2-yl)oxy)-5,6,6a,7,8,9,io,i2-octahydrobenzo[e]pyrido[i,2-a][i,4]diazepin-3- yl)oxy)butanamido)-i-methyl-iff-imidazole-2-carboxylic acid (40) (110 mg, 0.170 mmol) in AyV- d i m e t h y 1 f 0 r m a m i d e (4 mL) was charged with i-(3-dimethylamino- propyl)-3-ethylcarbodiimide hydrochloride (59 mg, 0.31 mmol) and 4-(dimethyl- amino)pyridine (47 mg, 0.38 mmol). The reaction mixture was stirred at room temperature for 30 min. Methyl 5-aminobenzo[b]thiophene-2-carboxylate (32 mg, 0.15 mmol) was then added and the resulting mixture was stirred at room temperature for 16 h. This was then poured onto ice-water (40 mL) and extracted with ethyl acetate (3 x 100 mL). The combined organic extracts were sequentially washed with an aqueous solution of citric acid (1 M, 60 mL), a saturated aqueous solution of sodium hydrogen carbonate (70 mL), water (70 mL) and brine (70 mL). The organic layer was then dried over sodium sulfate, filtered and concentrated. The resulting residue was then purified by column chromatography (silica), eluting with ethyl acetate/dichloromethane (0% to 100%), followed by methanol/ dichloromethane (from 0% to 10%), to give the title compound (50 mg, 39%) as a yellow oil. MS (ES+): m/z = 845 (M+H)+; LCMS (Method A): ?R = 8.22 min.

As the paragraph descriping shows that 20699-85-8 is playing an increasingly important role.

Reference£º
Patent; FEMTOGENIX LIMITED; THURSTON, David Edwin; JACKSON, Paul Joseph Mark; (294 pag.)WO2020/49286; (2020); A1;,
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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

General procedure: To an 10 mL vial reaction vessel equipped with a magnetic stirring bar was added pyridazine-3-carboxylic acid (0.6 mmol, 1.0 eq), aryl- and heteroaryl-bromides (1.2 mmol, 2.0 eq), Pd(PPh3)4 (35 mg, 0.03 mmol, 5.0 mol %), Cu2O (84 mg, 0.6 mmol, 1.0 eq), Li2CO3 (107 mg, 1.8 mmol, 3.0 eq), 3A MS (200 mg) and DMA (4.0 mL). The mixture was stirred at 160 C for 24 h under N2. After the reaction was complete, the mixture was washed with brine and extracted with ethyl acetate three times. The combined organic layer was dried with anhydrous MgSO4 and evaporated in vacuum. The residue was purified by silica gel flash chromatography to produce the desired products (ethyl acetate / petroleum ether = 1/5 – 1/1), the eluent need bubbled NH3 five seconds. The eluent of TLC (ethyl acetate / petroleum ether 1:1) need bubbled NH3 two seconds.

The synthetic route of 4923-87-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Wang, Shengqiang; Lu, Hongtao; Li, Jingya; Zou, Dapeng; Wu, Yusheng; Wu, Yangjie; Tetrahedron Letters; vol. 58; 12; (2017); p. 1107 – 1111;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.17347-32-9,6-Bromobenzothiophene,as a common compound, the synthetic route is as follows.

Compound TDI01106-1 (2.50 g, 7.04 mmol) and cuprous cyanide (1.58 g, 17.6 mmol) were dissolved in Nmethylpyrrolidone(25 mL), the reaction was performed under microwave radiation at 200C for 1 hour. Thin layerchromatography (petroleum ether : ethyl acetate=5: 1) indicated the reaction was complete. The reaction solution wascooled to room temperature, followed by addition of water (100 mL), and was extracted with ethyl acetate (50 mL X 3).The combined organic phase was washed with saturated brine (80 mL X 3), dried over anhydrous sodium sulfate, filtered,concentrated under reduced pressure, and the residue was purified by column chromatography (petroleum ether : ethylacetate= 20:1), to afford compound TDI01106-2 (1.00 g, yellow solid, yield: 54.1%).1H NMR (400 MHz, CDCl3) delta 8.22 (s, 1H), 7.90 (d, J = 8.4 Hz, 1H), 7.72 (d, J = 5.6 Hz, 1H), 7.60 (dd, J = 8.4, 1.2 Hz,1H), 7.42 (d, J = 5.6 Hz, 1H).

The synthetic route of 17347-32-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Beijing Tide Pharmaceutical Co., Ltd.; Zhao, Yanping; Wang, Hongjun; Li, Gong; Jiang, Yuanyuan; Li, Xiang; Zhou, Liying; Liu, Yanan; (235 pag.)EP3421465; (2019); A1;,
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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

To a solution of 5-bromobenzo [b] thiophene (8.5 g, 40 mmoL) in 1, 4-dioxane (150 mL) was added 4, 4, 5, 5-tetramethyl-2- (1, 4-dioxaspiro [4.5] dec-7-en-8-yl) -1, 3, 2-dioxaborolane (10.6 g, 40 mmol), Pd (dppf) Cl2 (4.4 g, 6 mmol) and Cs2CO3 (19.5 g, 60 mmol) and the mixture was heated at 80 for 2 hours. Then filter off the solid, the filtrate was evaporated under reduced pressure and the residue was purified by column chromatography (PE: EA=25: 1) to give product as yellow solid (6.6 g in 61% yield). 1HNMR (400 MHz, DMSO-d6) deltaH 7.92 (d, J= 8.8 Hz, 1H), 7.89 (s, 1H), 7.74 (d, J= 5.2 Hz, 1H), 7.46 (dd, J = 8.8 Hz, 1.6 Hz, 1H), 7.43 (d, J = 5.6 Hz, 1H), 6.09 (t, J = 3.6 Hz 1H), 3.93 (s, 4H), 2.63 (t, J= 5.6 Hz, 2H), 2.40 (s, 2H), and 1.85 (t, J= 6.4 Hz, 2H). [M+H] += 273.0.

4923-87-9 5-Bromobenzothiophene 2776578, abenzothiophene compound, is more and more widely used in various.

Reference£º
Patent; BEIGENE, LTD.; WANG, Hexiang; GUO, Yunhang; REN, Bo; WANG, Zhiwei; ZHANG, Guoliang; ZHOU, Changyou; (353 pag.)WO2018/54365; (2018); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.20532-28-9,5-Aminobenzothiophene,as a common compound, the synthetic route is as follows.

A solution of 540 mg of benzo[b]thiophen-5-ylamine in 5 ml of diethyl ethoxymethylenemalonate is stirred at 130C for 1.5 hours. The reaction mixture is then diluted with ethyl acetate. It is washed with saturated aqueous sodium chloride solution, dried over sodium sulphate and concentrated in vacuo. The crude product is purified by column chromatography on silica gel with a hexane/ethyl acetate mixture. 1.88 g of product are obtained.1H-NMR (CDCl3): delta= 1.30-1.45 (6H); 4.20-4.38 (4H); 7.16 (1 H); 7.30 (1 H); 7.51 (1H); 7.58 (1H); 7.86 (1 H); 8.60 (1H) 11.12 (1 H).

As the paragraph descriping shows that 20532-28-9 is playing an increasingly important role.

Reference£º
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; WO2007/147578; (2007); A1;,
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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;,
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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;,
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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.

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);,
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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;,
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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

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;,
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