Category: benzothiophene

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

(C) To a solution of 5-bromo-1-benzothiophene (12 g, 56.31 mmol) in dry THF (300 mL) under an inert atmosphere was added isopropyl magnesium chloride-lithium chloride complex (1.3 M in THF; 150 mL, 195 mmol) in drop-wise fashion, and the resultant solution was stirred at rt, overnight. DMF (30 mL) was then added in drop-wise fashion and the resultant solution was stirred at rt for 30 min. Water (500 mL) was added and the resulting solution was extracted with ethyl acetate (3*500 mL). The combined organic extracts were concentrated under reduced pressure and the resultant residue was purified by silica gel chromatography (0-2% EtOAC/petroleum ether) to provide benzo[b]thiophene-5-carbaldehyde (6.9 g, 68%) as a yellow solid. 1H NMR (DMSO-d6) delta 10.12 (s, 1H), 8.32 (s, 1H), 8.01 (d, J=8.4 Hz, 1H), 7.86-7.89 (m, 1H), 7.57-7.61 (m, 1H), 7.47-7.50 (m, 1H).

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

Reference£º
Patent; Janssen Pharmaceutica NV; Liang, Yin; Demarest, Keith T.; (109 pag.)US2017/290800; (2017); A1;,
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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.

[0114] A mixture of 2-chloro-5-methyl-pyrimidin-4-ylamine (0.30 g, 2.1 mraol), 5- bromo-benzo[]thiophene (0.6 g, 2.8 mmol), Pd2(dba)3 (95 mg, 0.10 mmol), Xantphos (0.12 g, 0.20 mmol) and cesium carbonate (1.3 g, 4.0 mmol) was suspended in dioxane (25 mL) and heated at reflux under the argon atmosphere for 3 h. The reaction mixture was cooled to room temperature and diluted with DCM (30 mL) . The mixture was filtered and the filtrate concentrated in vacuo. The residue was purified by flash chromatography on silica gel (hexane to 30% EtOAc/hexane) to afford the title intermediate 13 (0.23 g, 40%) as a white solid. MS (ESI+): m/z 276 (M+H)+.

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; TARGEGEN, INC.; WO2007/53452; (2007); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.20532-33-6,5-Chlorobenzothiophene,as a common compound, the synthetic route is as follows.

PREPARATION 22 Preparation of 3-bromo-5-chlorobenzo[b]thiophene A solution of bromine (0.31 g, 1.95 mmol) in 1.0 ml glacial acetic acid was added to a stirred solution of 5-chlorobenzo[b]thiophene (0.300 g, 1.77 mmol) in glacial acetic acid (1.0 ml) under nitrogen atmosphere. The reaction was heated to 50 C. for 4 hours, the volatiles removed under reduced pressure, the residue diluted in methylene chloride, washed with aq. sodium bicarbonate and with brine and dried over sodium sulfate. Evaporation gave 0.335 g (76%) of a tan solid. mp 85-86 C., FDMS m/e=249 (M+2)., 20532-33-6

20532-33-6 5-Chlorobenzothiophene 11309754, abenzothiophene compound, is more and more widely used in various fields.

Reference£º
Patent; Eli Lilly and Company; US5576321; (1996); A;,
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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, 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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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.346592-74-3,7-Fluorobenzo[b]thiophene,as a common compound, the synthetic route is as follows.

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

As the paragraph descriping shows that 346592-74-3 is playing an increasingly important role.

Reference£º
Patent; Smith-Swintosky, Virginia L.; US2007/191450; (2007); A1;; ; Patent; Smith-Swintosky, Virginia L.; US2007/191452; (2007); A1;; ; Patent; Smith-Swintosky, Virginia L.; US2007/191459; (2007); A1;,
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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.,4923-87-9

EXAMPLE 9 N-[(5-bromobenzor[b]thien-3-yl)methyl]-sulfamide (Compound #15) 5-Bromobenzothiophene (1.60 g, 7.51 mmol) and dichloromethyl methyl ether (1.29 g, 11.3 mmol) were dissolved in anhydrous 1,2-dichloroethane (75 mL). Titanium tetrachloride (2.14 g, 11.3 mmol) was added, turning the solution dark. After one hour 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*100 mL). The extracts were concentrated and chromatographed (0 to 5% ethyl acetate in hexane) to yield 5-bromo-benzo[b]thiophene-3-carbaldehyde (1.32 g).

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

Reference£º
Patent; Parker, Michael H.; Reitz, Allen B.; Maryanoff, Bruce E.; US2006/47001; (2006); A1;,
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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.

Example 5 4-Fluorobenzo[b]thiophene was prepared starting from methyl thioglycolate and 2,6-difluorobenzaldehyde and then following a similar procedure to that given for 4-bromobenzo[b]thiophene in Example 9. A solution of bromine (9.2 ml) in dichloromethane (200 ml) was added dropwise under nitrogen at -5 C. over 30 minutes to a stirred mixture of 4-fluorobenzo[b]thiophene (24.7 g), sodium acetate (20 g) and dichloromethane (200 ml). The mixture was stirred at ambient temperature for 24 hours, then it was filtered and the solvent was removed in vacuo. The residue was dissolved in dichloromethane (50 ml), water (200 ml) and zinc dust (34.3 g) were added, then the mixture was stirred and heated under reflux for 10 hours, cooled to ambient temperature and filtered through Celite. The Celite was washed with ethyl acetate (200 ml) then the combined organic solutions were washed with saturated aqueous sodium chloride solution (100 ml), dried (MgSO4) and the solvents were removed in vacuo. The residue was purified by distillation in vacuo to give 3-bromo-4-fluorobenzo[b]thiophene (12.5 g) as a pale yellow oil, b.p. 70-85 C. a 0.53 mbar., 310466-38-7

310466-38-7 4-Fluorobenzo[b]thiophene 19088017, abenzothiophene compound, is more and more widely used in various fields.

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

N-Bromosuccinimide (5.73 g. 32.2 mmol) was added slowly into the stirred solution of 7- bromobenzo[b]thiophene (5.28 g, 24.78 mmol) in chloroform (25 mL) and acetic acid (25 mL) at 0 C. The resulting reaction mixture was stirred at 25 C for 24 h. The reaction was monitor by tlc and after completion of reaction the reaction mixture washed with saturated solution of Na2S2O3 (20 mL), NaHCO3 (20 mL) and water (10 mL). The organic part was dried over anhydrous sodium sulfate and concentrated under reduce pressure to give crude product which was purified by column chromatography on silica gel using hexane as eluent to afford 3,7- dibromobenzo[b]thiophene (4.7 g, 16.135 mmol) as white solid. ?H-NMR (400 MHz, CDC13): 0 7.80 (dd, J? = 8.2 Hz, J? = 0.9 Hz, 1H), 7.57 (d, J = 7.8 Hz, 1H), 7.52 (s, 1H), 7.36 (t, J = 7.8 Hz, 1H).

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; CURADEV PHARMA PRIVATE LTD.; BANERJEE, Monali; MIDDYA, Sandip; SHRIVASTAVA, Ritesh; RAINA, Sushil; SURYA, Arjun; YADAV, Dharmendra B.; YADAV, Veejendra K.; KAPOOR, Kamal Kishore; VENKATESAN, Aranapakam; SMITH, Roger A.; THOMPSON, Scott K.; WO2014/186035; (2014); A1;,
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3541-37-5, Benzo[b]thiophene-2-carboxaldehyde is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: Aromatic o-bromoacetal 1 (1.0 mmol) was placed in the roundbottomflask (50 mL) and dissolved in dry THF (8 mL) at -78 C underargon atmosphere. Next, n-BuLi (1.1 mmol, 2.5M in hexanes) wasadded. The resulting mixture was stirred for 15 min. under argon andthen aromatic aldehyde 2 (1.2 mmol) was added in dry THF. Stirringwas continued for 2 h at -78 C and the reaction mixture was warmedto room temperature. Saturated aqueous NH4Cl solution was added andthe solvent was evaporated. The residue was diluted with ethyl acetate(3×10 mL), washed with water (15 mL) and dried over anhydrousMgSO4. After filtration, ethyl acetate was removed in vacuum and thecrude product 3 was purified by column chromatography over silica gelwith a mixture of petroleum ether/acetone (4:1 v/v)., 3541-37-5

3541-37-5 Benzo[b]thiophene-2-carboxaldehyde 736500, abenzothiophene compound, is more and more widely used in various fields.

Reference£º
Article; Ba?czewski, Piotr; Kowalska, Emilia; Skalik, Joanna; Koprowski, Marek; Owsianik, Krzysztof; Ro?ycka-Soko?owska, Ewa; Ultrasonics Sonochemistry; vol. 58; (2019);,
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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 solution of AN-1 (6 g, 3.99 mmol) in EtOH (60 mL) is added N2H4 hydrate (31.1 ml). The mixture is heated to reflux for 45 min. The mixture is cooled to rt and then concentrated. The residue is dissolved in diethylene glycol (20 mL) and KOH (6.72 g, 120 mmol) is added. The mixture is stirred at 120 C for 18 h. The mixture is cooled to rt, diluted with EtOAc and the pH is adjusted with IN HC1 to pH < 4. The organic layers are washed with brine, dried over Na2S04 and concentrated. The residue is purified by Si02 flash chromatography to yield AN-2., 130-03-0

The synthetic route of 130-03-0 has been constantly updated, and we look forward to future research findings.

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; WO2015/160654; (2015); A1;,
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