Category: benzothiophene

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, [0142] Synthesis of Compound 2-1 [0143] 4.22 g (30 mmol) of thieno[3,2:b]thiophene is dissolved in 50 mL of dry ether, and the resultant is added in dropwise fashion to 100 mL of dry ether solution in which 25 mL of 2.5M butyl lithium solution dissolved in hexane is contained and is cooled to 0 C. The temperature is slowly increased to room temperature (24 C.) and agitation for two hours is performed at room temperature. 10 g (62 mmol) of benzothiophene-3-aldehyde is slowly added in a dropwise fashion to the resultant haze solution and is agitated overnight. 100 mL of ammonium chloride saturated solution is added. Precipitated materials are filtered and the filtered product is washed with water and ether to a Compound 2-1 (yield 70%). [0144] 1H NMR (300 MHz, CDCl3): delta ppm 7.89 (m, 2H), 7.77 (m, 2H), 7.59 (s, 2H), 7.35 (m, 4H), 7.13 (s, 2H), 6.44 (d, 2H), 2.56 (d, 2H).

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

Reference£º
Patent; SAMSUNG ELECTRONICS CO., LTD.; PARK, Jeong Il; LEE, Bang Lin; LEE, Ji Youl; CHUNG, Jong Won; US2013/116447; (2013); A1;,
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.24434-84-2,Benzo[b]thiophene-3-carbonitrile,as a common compound, the synthetic route is as follows.

General procedure:To a stirred solution of benzo[b]thiophene-3-carbonitrile (1.23 g, 7.7 mmol) in appropriate anhydrous solvent (15 mL) were slowly added 3 equiv of bromine (1.2 mL, 23.1 mmol). The resulting mixture was stirred at room temperature overnight. If the reaction was not complete (as observed by TLC or 1H NMR), additional bromine was added (0.5 equiv per 0.5 equiv) until total consumption of the starting material. Then the mixture was partitioned between CH2Cl2 (120 mL) and 10% aqueous NaHCO3 solution (120 mL). To this biphasic solution was added dropwise, under vigorous stirring, saturated aqueous Na2S2O3 solution until discoloration of the organic medium. The organic layer was separated, and the aqueous layer was extracted twice with CH2Cl2 (2 ¡Á 50 mL). The combined extract was dried (MgSO4), filtered and concentrated under vacuum. The resulting residue was purified by flash chromatography (SiO2, cyclohexane/EtOAc 93:7) to afford the pure desired product.To a stirred solution of benzo[b]thiophene-3-carbonitrile (1.23 g, 7.7 mmol) in appropriate anhydrous solvent (15 mL) were slowly added 3 equiv of bromine (1.2 mL, 23.1 mmol). The resulting mixture was stirred at room temperature overnight. If the reaction was not complete (as observed by TLC or 1H NMR), additional bromine was added (0.5 equiv per 0.5 equiv) until total consumption of the starting material. Then the mixture was partitioned between CH2Cl2 (120 mL) and 10% aqueous NaHCO3 solution (120 mL). To this biphasic solution was added dropwise, under vigorous stirring, saturated aqueous Na2S2O3 solution until discoloration of the organic medium. The organic layer was separated, and the aqueous layer was extracted twice with CH2Cl2 (2 ¡Á 50 mL). The combined extract was dried (MgSO4), filtered and concentrated under vacuum. The resulting residue was purified by flash chromatography (SiO2, cyclohexane/EtOAc 93:7) to afford the pure desired product., 24434-84-2

As the paragraph descriping shows that 24434-84-2 is playing an increasingly important role.

Reference£º
Article; Liger, Francois; Pellet-Rostaing, Stephane; Popowycz, Florence; Lemaire, Marc; Tetrahedron Letters; vol. 52; 29; (2011); p. 3736 – 3739;,
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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

Compound 3 (255 mg, 1.062 mmol) and compound 4 (200 mg, 0.965 mmol) were dissolved in DMF (3.22 mL). EDC (222 mg, 1.158 mmol) was added to the reaction mixture, followed by DMAP (118 mg, 0.965 mmol) and the reaction was stirred at rt overnight. The reaction mixture was diluted with EtOAc and was washed with sat’d NH4Cl, brine, dried over Na2S04, filtered and concentrated. The crude product was purified by silica gel chromatography (0% to 40% EtOAc/hexanes) to obtain compound 5 as an orange-white solid (300 mg, 0.699 mmol, 72% yield). LCMS = 6.014 min (8 min method). Mass observed (ESI+): 430.05 (M+H). 1H NMR (400 MHz, DMSO-i): d 1.46 (s, 9H), 3.83 (s, 3H), 3.89 (s, 3H), 6.97 (d, J = 8.8 Hz, 2H), 7.79 (d, J = 9.0 Hz, 1H), 7.97 (d, J = 8.9 Hz, 1H), 8.18 (s, 1H), 8.49 (s, 1H), 9.14 (s, 1H), 9.98 (s, 1H)., 20699-85-8

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

Reference£º
Patent; IMMUNOGEN, INC.; MILLER, Michael, Louis; SHIZUKA, Manami; CHARI, Ravi, V.J.; (312 pag.)WO2019/133652; (2019); 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, Step A 2-Iodobenzothiophene Under a nitrogen atmosphere a stirred solution of 25.0 grams (0.186 mole) of benzothiophene in 250 ml of dry tetrahydrofuran was cooled to -65 C., and 69.8 ml (0.186 mole) of n-butyllithium (2.7M in hexane) was added dropwise keeping the reaction mixture temperature below -60 C. Upon completion of addition, the reaction mixture was stirred for five minutes and then was allowed to warm to 0 C. After this time a solution of 50.8 grams (0.200 mole) of iodine in 180 ml of tetrahydrofuran was added dropwise keeping the reaction mixture temperature below 10 C. Upon completion of addition, the reaction mixture was allowed to warm to ambient temperature where it was quenched with an aqueous solution saturated with sodium metabisulfite. The reaction mixture was placed in a separatory funnel, and the organic layer was separated. The organic layer was washed with one portion of an aqueous solution saturated with sodium metabisulfite and with one portion of an aqueous solution saturated with sodium chloride. The aqueous layers were combined and washed with diethyl ether. The ether washes were combined with the organic layer, and the combination was dried with sodium sulfate. The mixture was filtered, and the filtrate was concentrated under reduced pressure to a residue. The residue was dissolved in diethyl ether and reconcentrated under reduced pressure to a residue. The residue was dissolved in warm hexane and eluted through a column of silica gel. The elude was concentrated under reduced pressure to a volume of approximately 100 ml, and a solid crystallized from the solution. The mixture was cooled, and the solid was collected by filtration, yielding in two crops 18.9 grams of 2-iodobenzothiophene.

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

Reference£º
Patent; FMC Corporation; US5073564; (1991); A;,
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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., 130-03-0

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

Reference£º
Article; Zweig, Joshua E.; Ko, Tongil A.; Huang, Junrou; Newhouse, Timothy R.; Tetrahedron; vol. 75; 34; (2019);,
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1423-61-6, 7-Bromobenzo[b]thiophene is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Preparation 2; Benzo[/?]thiophene-7-boronic acid; Combine 7-bromobenzo[?]thiophene (300 g, 1.41 mmol) and triisopropylborate (403.6 g, 2.15 mmol) in anhydrous tetrahydrofuran (THF) (4000 mL) in a 12-L Morton flask fitted with a mechanical stirrer and cool under nitrogen in a dry-ice/acetone bath to – 70 0C. Add M-butyl lithium (1.6 M in hexane, 714 g, 1.68 mmol) dropwise at such a rate as to keep the internal temperature less than -67.5 0C. After the addition is complete, allow the reaction mixture to stir at this temperature for 1 hour. Remove the cooling bath and slowly add 4 L of water. Next, add concentrated HCl (75 mL) until the pH of the solution is about pH=2. Allow the slurry to stir for 1 hour. Add sufficient 5 N aqueous NaOH to adjust the pH of the mixture to about pH=12. Separate the layers and save the aqueous layer. Dilute the organic layer with 4 L of methyl-tert-butyl ether and extract with 1 L of 5 N aqueous NaOH. Separate the layers. Combine the aqueous layer with the previous aqueous extract. Wash the aqueous layer with additional methyl-tert-butyl ether (4 L). Separate the layers and transfer the aqueous layers to a 12 L 3-neck round bottom flask fitted with a mechanical stirrer. Cool the solution to +5 0C with an ice-water bath. Add concentrated HCl slowly until the pH of the solution is about pH = 2. Stir the mixture for 30 min and filter off the resulting solid. Rinse the solid on the funnel twice with 2 L of water and allow to air-dry for 30 min. Place the solid in a vacuum oven at 50 0C and dry under vacuum overnight. Remove the yellow color by slurrying the dried solid with 2 L of w-heptane for 30 min. Again filter off the solid, air-dry for 30 min, and vacuum dry at 40 0C overnight to afford the title compound (188.8 g, 75 %) as a white solid. 1H NMR (400 MHz, CD3OD) delta 7.86 (d, J= 8 Hz, IH), 7.49-7.57 (m, 2H), 7.30- 7.39 (m, 2H).

1423-61-6, As the paragraph descriping shows that 1423-61-6 is playing an increasingly important role.

Reference£º
Patent; ELI LILLY AND COMPANY; WO2008/76705; (2008); 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.1423-61-6,7-Bromobenzo[b]thiophene,as a common compound, the synthetic route is as follows.

To a solution of 7-bromobenzo[b]thiophene (5.0 g, 24 mmol) in diethyl ether (50 mL) at 100 C under nitrogen was added dropwise t-BuLi (1.3 mol/L, 55 mL). The mixture was stirred at – 100 C for 15 min, and dry acetone (3.6 g, 48 mmol) was added dropwise at -100 C. The mixture was stirred at -100 C for 2 hours. TLC showed the reaction was complete and the formation of two products (about 1 : 1). The reaction mixture was quenched with saturated aqueous ammonium chloride (20 mL) dropwise at 0 C, and then extracted with ethyl acetate (3 x 50 mL). The combined organic layers were washed with brine (2 chi 50 mL), dried over anhydrous sodium sulfate, concentrated in vacuo and purified by silica gel column chromatography [petroleum ether: ethyl acetate = 40: 1] to give compound B-302 (0.80 g, 34% yield, the lower spot on TLC) as a yellow oil.

1423-61-6, 1423-61-6 7-Bromobenzo[b]thiophene 12045538, abenzothiophene compound, is more and more widely used in various fields.

Reference£º
Patent; FORUM PHARMACEUTICALS, INC.; ACHARYA, Raksha; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; COOK, Andrew, Simon; HARRISON, Bryce, Alden; KOENIG, Gerhard; MCRINER, Andrew, J.; (400 pag.)WO2016/100184; (2016); 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: An aqueous solution of NaOH (3M, 1.6mL) was added to a solution of aromatic ketone (1mmol) and 3-methoxybenzaldehyde (1.2 eq), in EtOH (1-2mL). The reaction was stirred at r.t for 18-24h. The reaction mixture was cooled in an ice-water bath and acidified to pH 2 with concentrated HCl (37%). The solid formed was filtered, washed with ethanol and then further purified by recrystallization from ethanol. When no precipitate occurred, the reaction mixture was extracted with dichloromethane and washed with water and brine. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. Column chromatography was then utilized to purify the desired product.

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

Reference£º
Article; Borsari, Chiara; Jimenez-Anton, Maria Dolores; Eick, Julia; Bifeld, Eugenia; Torrado, Juan Jose; Olias-Molero, Ana Isabel; Corral, Maria Jesus; Santarem, Nuno; Baptista, Catarina; Severi, Leda; Gul, Sheraz; Wolf, Markus; Kuzikov, Maria; Ellinger, Bernhard; Reinshagen, Jeanette; Witt, Gesa; Linciano, Pasquale; Tait, Annalisa; Costantino, Luca; Luciani, Rosaria; Tejera Nevado, Paloma; Zander-Dinse, Dorothea; Franco, Caio H.; Ferrari, Stefania; Moraes, Carolina B.; Cordeiro-da-Silva, Anabela; Ponterini, Glauco; Clos, Joachim; Alunda, Jose Maria; Costi, Maria Paola; European Journal of Medicinal Chemistry; vol. 183; (2019);,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.4923-87-9,5-Bromobenzothiophene,as a common compound, the synthetic route is as follows.

To toluene 1.6mL solution of tert-butyl 2-(4-fluoroanilino)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate 79mg were added ethanol 0.60mL, water 0.30mL, 5-bromobenzothiophene 61mg, sodium hydrogen carbonate 48mg and tetrakis(triphenylphosphine)palladium(0) 11mg at room temperature, and it was heated and refluxed for 6 hours. After the reaction mixture was cooled to room temperature, and ethyl acetate and water were added to it. The organic layer was separated and collected, dried over anhydrous magnesium sulfate after washing with saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [Trikonex company, Flash Tube 2008, eluent; hexane:ethyl acetate=5:1] to give tert-butyl 4-(benzothiophen-5-yl)-2-(4-fluoroanilino)benzoate. Trifluoroacetic acid 5.0mL was added to the obtained tert-butyl 4-(benzothiophen-5-yl)-2-(4-fluoroanilino)benzoate, and it was stirred at room temperature for 3 hours. The solvent was removed under reduced pressure, the obtained residue was refined by reversed-phase silica gel column chromatography [eluent; 80-100% acetonitrile/0.1% trifluoroacetic acid aqueous solution] to give 4-(benzothiophen-5-yl)-2-(4-fluoroanilino)benzoic acid 16mg of a yellow solid. 1H-NMR(DMSO-d6) delta value: 7.13(1H,dd,J=8.3,1.7Hz),7.19-7.27(2H,m),7.34-7.43(3H,m),7.52(1H,d,J=5.6Hz),7.56(1H,dd,J=8.5,1.6Hz),7 .81(1H,d,J=5.6Hz),8.00(1H,d,J=8.3Hz),8.07(1H,d,J=8.5Hz) ,8.10(1H,d,J=1.6Hz),9.66(1H,s),13.10(1H,s).

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

Reference£º
Patent; TOYAMA CHEMICAL CO., LTD.; EP1860098; (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.130-03-0,Benzo[b]thiophen-3(2H)-one,as a common compound, the synthetic route is as follows.

To AN-1 (6 g, 3.99 mmol)N2H4 hydrate (31.1 ml) was added to a solution in EtOH (60 mL).The mixture was heated to reflux and held for 45 min.The mixture was allowed to cool to rt and then concentrated.The residue was dissolved in diethylene glycol (20 mL) and EtOAc (EtOAc.The mixture was stirred at 120 C for 18 h.The mixture was cooled to rt, diluted with EtOAc and pH was adjusted to pH < 4 with 1 N HCl. The organic layer was washed with brine, dried over Na2EtOAcThe residue was purified by flash chromatography on SiO2 to yield AN-2. 130-03-0, As the paragraph descriping shows that 130-03-0 is playing an increasingly important role.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BAKONYI,JOHANNA; BRUNETTE,STEVEN RICHARD; COLLIN,DELPHINE; HUGHES,ROBERT OWEN; LI,XIANG; LIANG,SHUANG; SIBLEY,ROBERT; TURNER,MICHAEL ROBERT; WU,LIFEN; ZHANG,QIANG; (169 pag.)TW2018/38997; (2018); A;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem