Category: benzothiophene

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.

General procedure: IS-PPh3 (746 mg, 1.8 mmol) was dried by a vacuum pump for 2 h at 70 C. To a flask containing IS-PPh3 were added 4-methoxycarboxylic acid (152 mg, 1.0 mmol), BrCCl3 (357 mg, 1.8 mmol), benzylamine (129 mg, 1.2 mmol), triethylamine (0.14 mL, 1.0 mmol), and THF (4 mL). The obtained mixture was stirred for 6 h at 60 C under Ar atmosphere. After the reaction, diethyl ether (10 mL) and aq HCl (1 M, 2 mL) were added at 0 C and the obtained mixture was stirred for 15-30 min at room temperature. Then, the reaction mixture was poured into water (8 mL) and the obtained mixture was extracted with diethyl ether (10 mL¡Á4). The combined organic layer was washed with water (10 mL) and brine (10 mL), and then dried over Na2SO4. After removal of the solvent under reduced pressure, N-benzyl-4-methoxybenzamide was obtained in 93% yield with 99% purity, as estimated by 1H NMR measurement. For cinnamic and aliphatic amides (entries 18-25 in Table 2) and indole-2-carboxamide (entry 16 in Table 2), the reaction mixture was poured into water (8 mL) and the obtained mixture was extracted with chloroform (10 mL¡Á4). The combined organic layer was washed with water (10 mL) and brine (10 mL), and then dried over Na2SO4. After removal of the solvent under reduced pressure, N-benzylamide was obtained. or the recovery of IS-Ph3PO, NaCl (5.0 g) was added to the aqueous layer. The aqueous solution was extracted with CHCl3 (10 mL¡Á5) and the combined organic layer was dried over NaSO4. After removal of the solvent, IS-Ph3PO containing a trace amount of IS-Ph3P was obtained in 95% yield.

6314-28-9 Benzo[b]thiophene-2-carboxylic acid 95864, abenzothiophene compound, is more and more widely used in various fields.

Reference£º
Article; Kawagoe, Yuhsuke; Moriyama, Katsuhiko; Togo, Hideo; Tetrahedron; vol. 69; 19; (2013); p. 3971 – 3977;,
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360575-29-7, Methyl 4-bromobenzo[b]thiophene-2-carboxylate is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of methyl 4-bromobenzo[b]thiophene-2-carboxylate (101 g), sodium hydroxide (63 g), methanol (1200 ml) and water (600 ml) was stirred at ambient temperature for 16 hours, the methanol was removed in vacuo, and the resulting suspension was cooled to 0 C. and acidified by dropwise addition of concentrated hydrochloric acid. The mixture was stirred for 20 minutes and the resulting solid was collected by filtration, washed with water (3*250 ml) and dried in vacuo at 110-120 C. to give 4-bromobenzo[b]thiophene-2-carboxylic acid (62 g) as a cream solid which was used without further purification., 360575-29-7

The synthetic route of 360575-29-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Doyle, Kevin James; Kerrigan, Frank; Watts, John Paul; US2003/166628; (2003); A1;,
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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

To a stirring solution of diisopropylamine (2.374 g, 23.46 mmol) in THF (12 mL) at -70 C under nitrogen was added butyllithium (8.26 mL, 20.65 mmol, 2.5M solution in hexanes). After 15 minutes at -70 C was added 7- bromo-l-benzothiophene (4.0 g, 18.77 mmol, Intermediate X13) in THF (10 mL). The cooling bath was removed and reaction warmed to -30 C then returned to -70 C. To the colorless solution was added di-tert-butyl (6-((E)- (((S)-tert-butylsulfinyl)imino)methyl)-5-chloro-2-pyridinyl)imidodicarbonate (8.63 g, 18.77 mmol, Intermediate AA4) in THF (15 mL) at a rate not to exceed – 60 C. After 18 h of warming to 20 C, the reaction was quenched with sat. NH4C1 (20 mL). The reaction was then partitioned between EtOAc (120 mL) and sat NH4C1 (50 mL). The organic was the dried over MgS04, concentrated onto dry silica (30 g) under reduced pressure, then purified by silica gel chromatography (330 g) eluting products with 10 to 50% EtOAc in hexanes to afford tert-butyl (6-((7-bromo-l-benzothiophen-2-yl)(((S)-tert- butylsulfinyl)amino)methyl)-5-chloro-2-pyridinyl)carbamate (6.0 g) as a white solid., 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; AMGEN INC.; ASHTON, Kate; BARTBERGER, Michael D.; BOURBEAU, Matthew Paul; CROGHAN, Michael D.; FOTSCH, Christopher H.; HUNGATE, Randall W.; KONG, Ke; NISHIMURA, Nobuko; NORMAN, Mark H.; PENNINGTON, Lewis D.; REICHELT, Andreas; SIEGMUND, Aaron C.; TADESSE, Seifu; ST. JEAN, David Jr; YANG, Kevin C.; YAO, Guomin; WO2013/173382; (2013); A1;,
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Benzothiophene | C8H6S – PubChem

360576-01-8, Methyl 6-bromobenzo[b]thiophene-2-carboxylate is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

LiOH.H20 (1.85g, 44mmol) and water (20mL) were added to a stirred solution of 6-bromo-benzo[b]thiophene-2-carboxylic acid methyl ester (I-25a: 2.4g, 8.85mmol) in THF (25mL) at room temperature. The resulting mixture was stirred at room temperature for 2 hours. The reaction was monitored by TLC (100% ethyl acetate). The reaction mixture was concentrated, acidified with 2N HCl, filtered and the residue was washed with n-hexane to afford 1.9g of the product (84% yield).1H NMR (DMSO-D6, 300 MHZ): 814.0-14.03 (b, 1H), 8.4-8.39 (d, 1H), 8.28- 8.1 (d, 1H), 8.18-8.0 (d, 1H), 7.78-7.62 (dd, 1H). LCMS Purity: 99%, m/z = 255.9 (M+l)

360576-01-8, 360576-01-8 Methyl 6-bromobenzo[b]thiophene-2-carboxylate 22474078, abenzothiophene compound, is more and more widely used in various fields.

Reference£º
Patent; NOVARTIS AG; BOCK, Mark Gary; GAUL, Christoph; GUMMADI, Venkateshwar Rao; SENGUPTA, Saumitra; WO2012/149413; (2012); A1;,
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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.

Benzo[]thiophene-2-thiol (72): Compound 71 (1.75 g,13.0 mmol) was dissolved in 40 niL of dry Et2O under N2 and the solution was cooled to -4O0C. nBuLi (2.5 M solution in hexane, 5.7 mL, 14.3 mmol) was added and the reaction mixture was allowed to warm up to O0C during Ih and then sulfur (0.414g, 13.0 mmol) was added in one portion. The solution was allowed to slowly warm up to RT over 3 h. Excess of 10% HCl was added and the reaction mixture was stirred for 20 min. The thiol was extracted with ether, washed with brine, dried over Na2SO4 and concentrated to afford 2.0 g of crude compound 72 which was used in the next step without further purification., 95-15-8

95-15-8 Thianaphthene 7221, abenzothiophene compound, is more and more widely used in various fields.

Reference£º
Patent; HYDRA BIOSCIENCES, INC.; WO2006/122156; (2006); A2;,
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Benzothiophene | C8H6S – PubChem

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, Dissolve 4-bromo-1, 2-bis-bromomethyl-benzene (J. Org. Chef., 1418-1421, 1985; 3.42 g, 9.96 mmol) in a 2 to 1 mixture of ethanol (EtOH) and THF (1196 mL) and heat the solution to 70C with stirring. Add a solution of Na2S. 9H2O (2.63 g, 10.96 mmol) in water (40 mL), dropwise, over 10 hours using a syringe pump. Continue to heat and stir for another 10 hours. Cool to room temperature and remove the organic solvent under reduced pressure. Add water (200 mL) to the residue and extract the aqueous layer with EtOAc (3 x 200 mL). Combine the organic layers and dry with Na2S04, filter, concentrate and purify by flash column chromatography (silica gel, hexanes) to give 1.27 g of 5-bromo-1, 3-dihydro-benzo [c] thiophene (59%). Dissolve 5-bromo-1, 3-dihydro-benzo [c] thiophene (1. 25 g, 5.79 mmol) in methanol (25 mL) and add oxone (10.7 g, 17. 4 mmol). Stir the reaction mixture for 2 hours at 0C and then add a 1M aqueous sodium bisulfite solution (100 mL). Stir the reaction mixture for 10 minutes and add saturated NaHCO3 solution (200 mL). Extract the aqueous layer with CH2C12 (3 x 100 mL). Combine the organic layers and dry with Na2S04, filter, concentrate and purify by flash column chromatography (silica gel, 0-5% MeOH/CH2Cl2) to give 930 mg of 5-bromo-1, 3-dihydro-benzo [c] thiophene 2, 2-dioxide (65%). Dissolve 5-bromo-1, 3-dihydro-benzo [c] thiophene (860 mg, 3.50 mmol) and hexamethylditin (3 eq. ) in toluene and add tetrakis (tripheuylphosphine) palladium (0) (Pd (PPh3) 4, 0.1 eq. ). Flush the flask with N2 and then heat the mixture to 120C with stirring. Continue to heat the mixture for 5 hours and then cool to room temperature. Add water (50 mL) and extract aqueous layer with EtOAc (3 x 50 mL). Combine the organic layers and dry with Na2SO4, filter, concentrate and purify by flash chromatography (silica gel, 10-30% EtOAc/hexane) to give 1.22 g of the title compound (100%).

The synthetic route of 351005-12-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ELI LILLY AND COMPANY; WO2004/9086; (2004); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

95-15-8, Thianaphthene is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

At -78 C,16.6 g (124 mmol) of benzothiophene (compound of formula 2) was dissolved in 200 mL of tetrahydrofuran.Add 78.5 mL (937 mmol) of n-butyllithium,The mixture was stirred at -78 C for 1.5 hours.Will be 23.95g (118mmol)5-bromo-2-fluorobenzaldehyde (formula 1 compound) is solubleIn 300 mL of tetrahydrofuran,And mixing it with the above benzothiophene solution,Stirring was continued for 2 hours at -78 C.Water and diethyl ether were added to the reaction mixture.Separating the organic phase,And dried with magnesium sulfate,It is then filtered and dried under vacuum.The obtained crude product was purified by column chromatography (ethyl acetate-hexane).Obtaining benzo[b]thiophene-2-methanol,Alpha-(5-bromo-2-fluorophenyl) (compound of formula 3) 35.4 g;Purity 99.5%; yield 89%;, 95-15-8

As the paragraph descriping shows that 95-15-8 is playing an increasingly important role.

Reference£º
Patent; Anqing Qichuang Pharmaceutical Co., Ltd.; Wu Xueping; Hai Wei; (13 pag.)CN108276396; (2018); A;,
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Benzothiophene | C8H6S – PubChem

4923-87-9, 5-Bromobenzothiophene is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a stirred mixture of 5-bromobenzthiophene (22.5 g, 105.6 mmol) and the acid chloride (17.4 ml, 141.3 mmol) in 135 ml benzene at 0 C., SnCl4 (43.1 ml, 368 mmol) was added in 2 h. Stirring was continued for 4 hours at the same temperature. The reaction mixture was poured into a mixture of 95 ml concentrated HCl (36-38%) in ice. The reaction mixture was extracted with EtOAc and the organic layer was washed with H2O (3*), 1N NaOH (1*), 5% NaHCO3 and H2O (2*). The EtOAc fraction was dried (MgSO4). The drying agent was removed by filtration and the solvent by evaporation under reduced pressure. The residue was recrystallized from 950 ml MeOH and chromatographed with Et2O/petroleum ether 1/1 as eluent to give 23.3 g (68%) of the acylated benzthiophene., 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; SOLVAY PHARMACEUTICALS B.V.; US2006/122189; (2006); 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.360576-01-8,Methyl 6-bromobenzo[b]thiophene-2-carboxylate,as a common compound, the synthetic route is as follows.

Ester 9 (6.8 g, 25.0 mmol) was dissolved in THF (anhydrous, 50 mL) and cooled to 0 oC. Lithium dimethylammonium borohydride3 (50 mL, 50.0 mmol, 1.0 M THF/hexane) was added drop-wise. After 5 min of stirring, the reaction was complete as judged by TLC and was quenched with HCl (3.0 M) under vigorous stirring until the evolution of gas ceased. The organic layer was separated, and the aqueous layer extracted with EtOAc (3x). The combined organic layers were washed with water and brine followed by drying (Na2SO4). Evaporation of solvent gave a yellow solid, which was recrystallized from isopropanol/water to give the desired primary alcohol as white crystals. (5.7 g, 94% yield), mp 111-113 oC. IR (thin film, cm-1) 3203, 3071, 2901, 2853, 1577, 1523, 1444, 849, 841; 1H NMR (CDCl3) delta 7.95 (d, J = 1.5 Hz, 1H), 7.57 (d, J = 8.5 Hz, 1H), 7.44 (dd, J = 1.5, 8.5 Hz, 1H), 7.17 (d, J = 1.0 Hz, 1H), 4.91 (s, 2H), 1.97 (br s, 1H); 13C NMR (CDCl3) delta 145.8, 141.6, 138.5, 128.0, 125.1, 124.8, 121.1, 118.3, 60.9; HRMS (EI) for C9H7BrOS [M]+ calcd, 241.9401, found, 241.9404 (error = 1.2 ppm)., 360576-01-8

360576-01-8 Methyl 6-bromobenzo[b]thiophene-2-carboxylate 22474078, abenzothiophene compound, is more and more widely used in various fields.

Reference£º
Article; Zuckerman, Nathaniel B.; Kang, Xiongwu; Chen, Shaowei; Konopelski, Joseph P.; Tetrahedron Letters; vol. 54; 11; (2013); p. 1482 – 1485;,
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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 2-L three-necked round-bottomed flask containing a solution of 7-bromo-l-benzothiophene (50 g, 236 mmol, Intermediate XI 3) in THF (400 mL) at -78 C was added LDA (236 mL of a 1.8 M solution in THF, 472 mmol, Sigma- Aldrich, India) and the mixture was stirred at -78 C for 45 min. A solution of N-((S,E)-(2-chlorophenyl)methylidene)-2-methyl-2- propanesulfinamide (57.3 g, 236 mmol, Intermediate Yl) in THF (100 mL) was added dropwise and the mixture was stirred at -78 C for 16 h. Water (500 mL) was added, the mixture was allowed to warm to room temperature, and was extracted with EtOAc (2 x 500 mL and 2 x 200 mL). The combined organic layers were dried (Na2S04), filtered, and concentrated under reduced pressure. The resulting product was purified by column chromatography (basic alumina, 0% to 10% EtOAc/hexane to deliver (S)-N-((R)-(7-bromo-l-benzothiophen-2- yl)(2-chlorophenyl)methyl)-2-methyl-2-propanesulfinamide (25 g) as a pale- yellow liquid.

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

Reference£º
Patent; AMGEN INC.; ASHTON, Kate; BARTBERGER, Michael D.; BOURBEAU, Matthew Paul; CROGHAN, Michael D.; FOTSCH, Christopher H.; HUNGATE, Randall W.; KONG, Ke; NISHIMURA, Nobuko; NORMAN, Mark H.; PENNINGTON, Lewis D.; REICHELT, Andreas; SIEGMUND, Aaron C.; TADESSE, Seifu; ST. JEAN, David Jr; YANG, Kevin C.; YAO, Guomin; WO2013/173382; (2013); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem