Category: benzothiophene

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 Grignard reagent was prepared using 7-bromobenzo-[b] thiophene (1.0 g), magnesium (0.13g), a catalytic amount of iodine and tetrahydrofuran (3 mL) according to the general method. To the Grignard reagent solution was added a solution of 4-methylbenzaldehyde (0.62 g) in tetrahydrofuran (5 mL) at 0C under an argon atmosphere. The reaction mixture was stirred at room temperature overnight and a saturated ammonium chloride aqueous solution was added to the mixture. The mixture was extracted with diethyl ether, and the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on aminopropylated silica gel (eluent: tetrahydrofuran). Further purification by column chromatography on silica gel (eluent; n-hexane/ethyl acetate = 6/1) gave the title compound (0.68 g) as yellow oil. 1H-NMR (CDCl3) delta ppm: 2.32 (3H, s), 2.38 (1H, d, J=3.6Hz), 6.11 (1H, d, J=3.4Hz), 7.10-7.20 (2H, m), 7.30-7.45 (5H, m), 7.45-7.50 (1H, m), 7.70-7.80 (1H, m)

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; Kissei Pharmaceutical Co., Ltd.; EP1724277; (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.20699-85-8,Methyl 5-aminobenzo[b]thiophene-2-carboxylate,as a common compound, the synthetic route is as follows.

A mixture of 500 mg of methyl 5-aminobenzo[b]thiophene-2-carboxylate, 320 mg of acetic anhydride, 623 mgof diisopropylethylamine, and 10 ml of dichloromethane was stirred for 4 hours at room temperature. The reaction mixturewas washed with an aqueous saturated sodium hydrogen carbonate solution and saturated saline, dried over magnesiumsulfate, and concentrated under reduced pressure. The residues were subjected to silica gel column chromatography,thereby obtaining 449 mg of methyl 5-(acetylamino)benzo[b]thiophene-2-carboxylate., 20699-85-8

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

Reference£º
Patent; Sumitomo Chemical Company Limited; MUKUMOTO, Fujio; TAMAKI, Hiroaki; KUSAKA, Shintaro; IWAKOSHI, Mitsuhiko; EP2926660; (2015); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

20532-33-6, 5-Chlorobenzothiophene is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

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 85-86C., 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; US5741789; (1998); A;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

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, Synthesis of methyl 4-aminobenzoate esters 5a-d and 11a-b The synthesis of 3-[(4-methoxycarbonylphenyl)aminomethyl]benzothiophene 5a will be used as an example for the synthesis of secondary amines 5a-d and 11 a-b. Benzothiophene-3- carbaldehyde 3a (406 mg, 2.5 mmol, 1 equiv) was dissolved in ethanol (15 mL) and to this solution were added glacial acetic acid (751 mg, 12.5 mmol, 5 equiv) and methyl 4- aminobenzoate (454 mg, 3 mmol, 1 .2 equiv). This reaction mixture was stirred for one hour at refluxing conditions after which it was cooled to 0C. Sodium cyanoborohydride (471 mg, 7.5 mmol, 3 equiv) was added and the reaction mixture was allowed to warm to room temperature. After one hour the mixture was poured in to brine (15 mL) and three times extracted with EtOAc (15 mL). The combined organic fraction was thereafter three times washed with brine (15 mL), dried (MgS04), filtered and evaporated under vacuum. Purification through recrystallization from ethanol yielded 3-[(4- methoxycarbonylphenyl)aminomethyl]-benzothiophene 5a (520 mg, 1 .75 mmol, 70%) as a white powder. For secondary amine 5b a solvent mixture of ethanol/CH2CI2(1 /1 ) was used as solvent for the reaction. 5a: 3-[(4-methoxycarbonylphenyl)aminomethyl]benzothiophene 70% as white powder; recrystallization from EtOH; m.p. 127C;1H-NMR (300 MHz, CDCI3): delta = 3.84 (s, 3H); 4.48 (s(broad), 1 H); 4.58 (d, J = 5.0 Hz, 2H); 6.62 (d, J = 8.8 Hz, 2H); 7.32 (s, 1 H); 7.35-7.43, 7.73-7.81 and 7.86-7.90 (3 m, 2H, 1 H and 3H);13C-NMR (75 MHz, CDCI3): delta = 42.2, 51 .7,1 1 1 .8, 1 19.0, 121 .7, 123.2, 124.1 , 124.4, 124.8, 131 .7, 132.8, 137.8, 141 .0, 151 .7 and 167.4; IR (cm”1): v = 3379 (N H); 1685 (C=0); MS (70 eV): m/z (%) = 296 (100) [M”- H]; HRMS (ESI)Anal. Calcd. for Ci7H14N02S 296.0751 [M”- H], Found 296.0760.

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

Reference£º
Patent; UNIVERSITEIT GENT; DE VREESE, Rob; D’HOOGHE, Matthias; (52 pag.)WO2016/110541; (2016); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

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

General procedure: Compound 5 A (100 mg, 0.241 mmol) and amine 12 (43.7 mg, 0.289 mmol) were dissolved in DMF (1.61 mL). EDC (69.2 mg, 0.361 mmol) was added to the solution at rt, followed by DMAP (14.70 mg, 0.120 mmol) and was stirred overnight. Water was added to the reaction mixture to precipitate the product. The resulting slurry was stirred for 15 min. The solution was filtered and the solid was dried under vacuum/N2 for 2 h to obtain compound 13 as an off white solid (127 mg, 0.231 mmol, 96% yield). LCMS = 6.408 min (8 min method). Mass observed (ESI+): 549.15 (M+H). 1H NMR (400 MHz, DMSO-76): d 1.31 (s, 6H), 1.46 (s, 9H), 2.45 (s, 3H), 3.48 (d, 7 = 6.3 Hz, 2H), 3.83 (s, 3H), 6.97 (s, 2H), 7.72 – 7.79 (m, 1H), 7.92 (d, 7 = 8.8 Hz, 1H), 8.11 (d, 7 = 3.7 Hz, 1H), 8.31 – 8.41 (m, 2H), 8.70 (t, 7 = 6.3 Hz, 1H), 9.14 (s, 1H), 9.94 (s, 1H)., 20699-85-8

Big data 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;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.89673-36-9,tert-Butyl benzo[b]thiophen-2-ylcarbamate,as a common compound, the synthetic route is as follows.

89673-36-9, Example 236; A solution of compound 235 (0.250 g, 1.00 mmol) was stirred in 4 M HCl solution in 1,4-dioxane (3 mL) at room temperature for 2 hrs at which time thin layer chromatography (DCM/Hexanes) indicated the reaction was complete. The reaction mixture was cooled to room temperature and concentrated under vacuum. The residue was diluted with acetonitrile, sonicated, and concentrated to afford compound 236 as a grey solid 0.24 g (91%). HPLC-MS tR=1.5 Min (UV254nm). Mass calculated for formula C8H7NS, M+ 149.21, observed LC/MS m/z 150.40 (M+H).

The synthetic route of 89673-36-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Schering Corporation; US2007/117804; (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 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

As the paragraph descriping shows that 130-03-0 is playing an increasingly important role.

Reference£º
Article; Zweig, Joshua E.; Ko, Tongil A.; Huang, Junrou; Newhouse, Timothy R.; Tetrahedron; vol. 75; 34; (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.89673-36-9,tert-Butyl benzo[b]thiophen-2-ylcarbamate,as a common compound, the synthetic route is as follows.

89673-36-9, C. Benzo[b]thiophen-2-ylamine hydrochloride (1e). Compound 1d (1.45 g, 5.81 mmol) was added to a solution of HCl in dioxane (4 N, 20 mL). The mixture was stirred at room temperature until all the starting material was consumed. The mixture was diluted with diethyl ether, and the product was collected by filtration and washed with diethyl ether to give an off white solid (0.89 g, 83%). 1H NMR (DMSO-d6): delta 6.43 (s, 1H), 6.8-7.2 (br s, 3H) superimposed on 7.05 (m, 1H) and 7.20 (m, 1H), 7.45 (d, 1H) and 7.66 (d, 1H); MS: m/z 150.1 (MH+).

As the paragraph descriping shows that 89673-36-9 is playing an increasingly important role.

Reference£º
Patent; Macielag, Mark J.; McNally, James J.; US2010/160289; (2010); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

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

General procedure: General operating procedure: under N2 protection, 20 mL anhydrous tetrahydrofuran was added into the flask containing 2.5 mmol matrine. Then the flask was cooled in icy brine solution for 10-15 min. Next, 5 mmol LDA was added dropwise, following a reaction at room temperature for 30 min. After an icy-salt bath, 5 mmol aromatic aldehyde was added, following a reaction at room temperature for 3 h. Then, a certain amount of water was added for quenching. After the pH value was adjusted to 7-8 by 3N HCl, water of three fold volume was added. Subsequently, the solution obtained was extracted with CH2Cl2, and the extract was detected using thin-layer chromatography (TLC). The organic layer was dried with anhydrous Na2SO4, and concentrated into oily residues. By using ethyl acetate and CH2Cl2 (with the volume ratio of 1:3) as eluant, the residue was purified with silica-gel column chromatography. Finally, the products of 3a~3ac were obtained, with the yields of 32-67%., 5381-20-4

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

Reference£º
Article; Li, Zheng; Wu, Lichuan; Cai, Bin; Luo, Mengyang; Huang, Mengtian; Ur Rashid, Haroon; Yang, Yuwen; Jiang, Jun; Wang, Lisheng; Medicinal Chemistry Research; vol. 27; 8; (2018); p. 1941 – 1955;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

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 500 mg of methyl 4-bromobenzo[b]thiophene-2-carboxylate, 161 mg of methylboronic acid, 1.17g of potassium phosphate, 151 mg of a [1,1?-bis(diphenylphosphino)ferrocene]palladium (II) dichloride dichloromethaneadduct, and 6 ml of 1,4-dioxane, and 0.1 ml of water was stirred for 3 hours at 100C under a nitrogen atmosphere. Afterbeing cooled to room temperature, the reaction mixture was concentrated under reduced pressure. Chloroform andwater were added to the residues, and insoluble matter was separated by filtration. The filtrate was extracted usingchloroform, and the organic layer was washed with saturated saline, dried over magnesium sulfate, and then concentratedunder reduced pressure. The residues were subjected to silica gel column chromatography, thereby obtaining 340 mgof methyl 4-methylbenzo[b]thiophene-2-carboxylate., 360575-29-7

As the paragraph descriping shows that 360575-29-7 is playing an increasingly important role.

Reference£º
Patent; Sumitomo Chemical Company Limited; MUKUMOTO, Fujio; TAMAKI, Hiroaki; KUSAKA, Shintaro; IWAKOSHI, Mitsuhiko; EP2926660; (2015); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem