Heterocyclic Building Blocks-Benzothiophene

24434-84-2, Benzo[b]thiophene-3-carbonitrile is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: In an oven-dried Schlenk tube equipped with a magnetic stir bar, the photocatalyst [Ir(dF-CH3-ppy)2(dtbpy)]PF6 (PC-1) (5.1 mg, 0.005 mmol, 1.0 mol%) was dissolved in MeCN (0.4 mL) andwater (0.1 mL) under an atmosphere of dry argon. In the absence of light, the respectivebenzothiophene (0.50 mmol, 1.0 equiv) and alkene (1.50 mmol, 3.0 equiv) were added in anargon stream. The reaction mixture was degassed by three freeze-pump-thaw cycles and thetube was finally backfilled with argon. The reaction was stirred under irradiation with visiblelight from two 30 W Kessil LED (lambdamax = 455 nm, see chapter 1.2 for emission spectrum). Afterthe indicated time, the solvent was removed in vacuo and the residue was purified by flashcolumn chromatography on silica gel to afford products 3a-3o as (mostly) inseparablemixtures of diastereomers.

The synthetic route of 24434-84-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Strieth-Kalthoff; Henkel, Christian; Teders, Michael; Kahnt, Axel; Knolle, Wolfgang; Gomez-Suarez, Adrian; Dirian, Konstantin; Alex, Wiebke; Bergander; Daniliuc, Constantin G.; Abel; Guldi, Dirk M.; Glorius; Chem; vol. 5; 8; (2019); p. 2183 – 2194;,
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 solution of 4-((tert-butoxycarbonyl)amino)-1-methyl-1H-pyrrole-2-carboxylic acid (127 mg, 0.530 mmol) in N,N-dimethylformamide (i mL) was charged with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (185 mg, 0.960 mmol) and4-(dimethylamino)pyridine (147 mg, 1.20 mmol). The reaction mixture was stirred at room temperature for 4 h. Methyl 5-aminobenzo[b]thiophene-2-carboxylate (100 mg, 0.480 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 withethyl acetate ( x 100 mL). The combined organic extracts were sequentially washed with an aqueous solution of citric acid (i 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 to give the title compound (i8 mg, 90%) as a cream solid. The product was carried through to the nextstep without any further purification.MS (ES+): m/z = 430 (M+H) LCMS (Method B): tR = 4.07 mm.

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

Reference£º
Patent; FEMTOGENIX LIMITED; JACKSON, Paul Joseph Mark; THURSTON, David Edwin; RAHMAN, Khondaker Mirazur; (121 pag.)WO2017/32983; (2017); 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

12255] A mixture of 500 mg of methyl 5-aminobenzo[b]thiophene-2-carboxylate, 552 mg of methanesulfonyl chlo-ride, 623 mg of diisopropylethylamine, and 10 ml of dichlo-romethane was stirred for 4 hours at room temperature. Afterthe reaction mixture was concentrated under reduced pressure, water was added to the residues, and the precipitatedsolids were collected by filtration. The obtained solids werewashed with water and hexane and dried under reduced pressure, thereby obtaining 449 mg of methyl 5-[bis(methylsul-fonyl)amino]benzo[b]thiophene-2-carboxylate.

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; US2015/282482; (2015); A1;,
Benzothiophene – Wikipedia
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

A mixture of 900 mg of methyl 6-bromobenzo[b]thiophene-2-caboxylate, 2.28 ml of diisopropylamine, 116 mgof dichlorobis(triphenylphosphine)palladium (II), 32 mg of copper iodide (I), 0.92 ml of trimethylsilyl acetylene, and 15ml of toluene was stirred for 20 hours at room temperature under a nitrogen atmosphere. The filtrate was concentratedunder reduced pressure, the residues were subjected to silica gel column chromatography, thereby obtaining 590 mgof methyl 6-(trimethylsilylethynyl)benzo[b]thiophene-2-carboxylate

The synthetic route of 360576-01-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Sumitomo Chemical Company Limited; MUKUMOTO, Fujio; TAMAKI, Hiroaki; KUSAKA, Shintaro; IWAKOSHI, Mitsuhiko; EP2926660; (2015); 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

To a stirred solution of JV-Boc-2-AH (0.11 mmol) in ethanol (5 mL) was added30 triethylamine (0.16 mmol) and 3-benzothiophene carboxaldehyde (0.13 mmol). The reaction mixture was stirred at rt for 6 h, after which the solvent was removed under reduced pressure and the reaction mixture was further subjected to flash chromatography over silica gel using a gradient of 5:95 – 30:70 (MeOH:DCM saturated with ammonia) yielding N”-tert-butyl-4-(benzothiophen-3-yl)-4,5,6,7-tetrahydro-lH-imidazo[4,5- c]pyridine-2-ylcarbamate. (28.5 mg; 70%) as a white solid. 1H NMR (400 MHz, CDCl3) delta 7.94 (d, J = 7.7 Hz, IH), 7.85-7.81 (m, IH), 7.42-7.29 (m, 2H), 6.83 (s, IH), 5.86 (bs, IH), 5.57 (s, IH), 2.96 (ddd, J= 13.1, 5.9, 2.1 Hz, IH), 2.82 (ddd, J= 13.1, 10.3, 4.7 Hz, IH), 2.63-2.53 (m, IH), 2.43-2.35 (m, IH), 2.17 (bs, IH), 1.02 (s, 9H); 13C NMR (100 s MHz, CDCl3) delta 150.8, 150.0, 140.8, 137.9, 134.9, 124.4, 124.2, 124.1, 123.0, 122.2, 117.8, 85.1, 50.8, 38.6, 27.4, 25.8; ir (KBr) 3453, 2928, 1722, 1627, 1369, 1326, 1263, 1138, 835, 765, 734 cm”1; HRMS found [M+H]+ 371.1547, C19H23N4O2S requires 371.1542. To a stirred solution of this tetrahydro-intermediate (III) (0.15 mmol) in chloroform (10 mL) was added chloranil (0.30 mmol) and the reaction mixture refluxedo for 20 h. Solvent was removed on a rotary evaporator and the residue obtained further purified by flash chromatography over silica gel with a gradient of 5:95 – 15:85 (MeOH:DCM saturated with ammonia) giving pure 4-(benzothiophen-3-yl)taulH- imidazo[4,5-c]pyridin-2-amine (25.5 mg; 64%) as a white solid. 1H NMR (400 MHz, CD3OD) delta 8.29 (s, IH), 8.27 (d, J = 6.5 Hz, IH), 8.10-8.07 (m, IH), 7.79-7.75 (m, IH),s 7.60 (d, J = 6.5 Hz, IH), 7.55-7.48 (m, 2H); 13C NMR (100 MHz, CD3OD) delta 159.2, 158.8, 151.7, 141.7, 137.8, 135.8, 133.3, 126.9, 126.6, 124.2, 123.5, 117.4, 114.6, 109.0; HRMS found [M+H]+ 267.0706, C14H11N4S requires 267.0704.

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

Reference£º
Patent; MACQUARIE UNIVERSITY; WO2009/152584; (2009); 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.17347-32-9,6-Bromobenzothiophene,as a common compound, the synthetic route is as follows.

In a 25 mL three-necked flask, magnesium (257 mg, 10.6 mmol) was suspended in THF,(1.7 mL) and heated to reflux. A solution of 6-bromobenzo[b]thiophene (1.5 g, 7.04 mmol) in THF (8.3 mL) was added dropwise. The reaction mixture was stuffed at reflux for 2 h, thencooled to 0C. N,N-Dimethylformamide (1.03 g, 1.09 ml, 14.1 mmol) was added dropwise and the reaction allowed to warm up to room temperature. The resulting green suspension was stirred overnight then concentrated. The residue was purified by chromatography over silica gel. One fraction was isolated and dried in vacuo, affording 821 mg (72%) of benzo[b]thiophene-6- carbaldehyde as a yellow oil.

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

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; LYNCH, Stephen M.; MARTIN, Rainer E.; NEIDHART, Werner; PLANCHER, Jean-Marc; SCHULZ-GASCH, Tanja; WO2014/86663; (2014); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

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 7-bromo-benzo [b] thiophene (5.28 g, 24.7 [MMOL)] was added pyridine-4- boronic acid (2.734 g, 22.24 [MMOL),] [K3PO4] (12.0 g, 56.5 [MMOL),] 37.5 mL of 1,4- dioxane and 3.8 mL of water. The mixture was placed under vacuum for several minutes and flushed with nitrogen. This was repeated 5 [TIMES. PD] (dppf) [CRI2 ] [CH2CI2] [(0. 909 G,] 1.11 [MMOL),] [PDCI2] (0. 1994 g, 1.124 [MMOL)] and 1,1″- bis (diphenylphosphino) ferrocene (0.6234 g, 1.124 [MMOL)] were purged in the same way using high vacuum. The catalyst was added to the reaction flask, which was purged again 3 times. The mixture was stirred at 80 [C] under nitrogen. After 1 day TLC showed much starting material remained. Additional [K3PO4] (2.3 g, 10.8 [MMOL)] was added after purging. Stirring at 80 C under nitrogen was continued for 12 to 14 hours and then at room temperature till the next day. The mixture was partitioned between water and ethyl acetate, filtered through Celite and the layers separated. The organic layer was concentrated in vacuum. The residue was redissolved in ethyl acetate, washed with water and dried over magnesium sulfate. Concentration in vacuum gave 6.06 g of dark oil. This was eluted from silica gel with a gradient of hexane and ethyl acetate to give 2.43 g of the title compound as a tan oil that crystallizes slowly, (m. p. [71-72C).] Elemental Analysis for: [C13HGNS 1/3 H2O] [CALC’D] : C, 71.86 ; H, 4.48 ; N, 6.45 Found: C, 71.93 ; H, 4.37 ; N, 5.66

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

Reference£º
Patent; WYETH; WO2004/24733; (2004); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

17402-83-4, Benzo[b]thiophen-4-amine is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

(Step 1) Sulfuryl chloride (0.30 ml) was added to ethyl 5-chloro-3-(methylthio)-1,2,4-triazine-6-carboxylate (234 mg), and the reaction solution was stirred at room temperature for 10 hours. The solvent was evaporated under vacuum, and the resultant residue was dissolved in THF (5 ml). Benzo[b]thiophen-4-amine (179 mg) and diisopropylethylamine (0.51 ml) were added, and the reaction solution was stirred at room temperature for 5 minutes. The reaction solution was diluted with ethyl acetate, and washed successively with an aqueous sodium bicarbonate solution and a saturated saline solution. After drying over anhydrous sodium sulfate, the solvent was evaporated under vacuum. The residue was purified by column chromatography on silica gel (developing solvent: hexane-ethyl acetate) to obtain ethyl 3-chloro-5-(benzo[b]thiophen-4-ylamino)-1,2,4-triazine-6-carboxylate as a white solid.

17402-83-4 Benzo[b]thiophen-4-amine 298484, abenzothiophene compound, is more and more widely used in various.

Reference£º
Patent; Taiho Pharmaceutical Co., Ltd.; SAKAMOTO, Toshihiro; MITA, Takashi; SHIBATA, Kazuaki; OGINO, Yoshio; KOMATANI, Hideya; EP2762476; (2014); 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

A solution of 18 g (134 mmol) of benzo[b]thiophene in 200 mL of chloroform was stirred and to this mixture was added 42.9 g (13.7 mL, 268 mmol) of bromine in 100 mL of chloroform dropwise at RT over 1.5 h. After stirring for 18 h, solid NaHCO3 was added to neutralize the hydrobromic acid. The organic layer was washed with water and Na2S2O8 and dried (MgSO4). On evaporation of the solvent solid was obtained which was crystallized from methanol to give 38.8 g (99%) of 2,3-dibromobenzo[b]thiophene.

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

Reference£º
Patent; SWITCH MATERIALS, INC.; Branda, Neil Robin; Finden, Jeremy Graham; Gauthier, Simon James; Hayek, Ali; Hope-Ross, Kyle Andrew; Senior, James Daniel; Spantulescu, Andreea; Sviridov, Serguei; US2014/256936; (2014); 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: Benzo[b]thiophene-3-carbaldehyde (40 mg, 0.25 mmol, 1.0 equiv),Pd(TFA) 2 (4.2 mg, 5 mol%), (4-FC 6 H 4 ) 3 P (9.5 mg, 12 mol%), DPEphos (8mg, 6 mol%), and Cs 2 CO 3 (122 mg, 0.375 mmol) were placed in atransparent Schlenk tube equipped with a stirring bar. The tube wasevacuated and filled with argon for three times. Degassed DMF (2.5mL) and tert-butyl bromide (51 mg, 0.375 mmol, 1.5 equiv) were add-ed via a gastight syringe. The reaction mixture was stirred under theirradiation of 36 W blue LEDs (distance app. 2.0-3.0 cm from thebulb) at r.t. for 24 h. The mixture was quenched with brine and ex-tracted with EtOAc (3 ¡Á 10 mL). The organic layers were combinedand concentrated under reduced pressure. The product was purifiedby flash column chromatography on silica gel using PE or a mixture of PEand EtOAc (10:1 v/v) as eluent; yield: 50.1 mg (92%); pale yellow liquid.

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

Reference£º
Article; Wang, Guang-Zu; Shang, Rui; Fu, Yao; Synthesis; vol. 50; 15; (2018); p. 2908 – 2914;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem