Category: benzothiophene

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: 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.

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);,
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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

Synthesis of 2-(phenylethynyl)benzo[b]thiophene-3-carbaldehyde (29c): Benzo[b]thiophene-3-carbaldehyde (27) (162 mg, 1.0 mmol) in THF (2 mL) was added to a solution of TMPZnCl.LiCl (2) (1.3 M in THF, 0.85 mL, 1.1 mmol) at 25 C. and the reaction mixture was then stirred at this temperature for 30 min according to TP 2. I2 (381 mg, 1.5 mmol) dissolved in dry THF (2 mL) was then dropwise added and the resulting mixture was stirred for 0.5 h. To the solution of freshly generated in situ 2-iodobenzo[b]thiophene-3-carbaldehyde, NEt3 (7 mL), Cul (8 mg, 4 mol %), Pd(dba)2 (17 mg, 3 mol %) and P(o-furyl)3 (14 mg, 6 mol %) in THF (2 mL) and phenylacetylene (254 mg, 1.5 mol, 1.5 equiv) were successively slowly added. The reaction mixture was stirred at rt for 2 h. The reaction mixture was quenched with a sat. aq. Na2S2O3 solution (10 mL) and with a sat. aq. NH4Cl solution (20 mL), extracted with diethyl ether (3¡Á50 mL) and driedanhydrous Na2SO4. After filtration, the solvent was evaporated in vacuo. Purification by flash-chromatography (CH2Cl2/n-pentane, 1:2) furnished compound 29c (165 mg, 63%) as a yellowish solid.m.p.: 104.9-106.5 C.1H-NMR (400 MHz, CDCl3) delta: 10.47 (s, 1 H), 8.69 (m, 1 H), 7.77 (m, 1 H), 7.60 (m, 2 H), 7.38-7.51 (m, 5 H).13C-NMR (100 MHz, CDCl3) delta: 185.6, 138.9, 138.5, 135.9, 135.2, 131.8, 129.8, 128.6, 126.8, 126.5, 124.9, 121.6, 121.3, 102.9, 80.0.MS (70 eV, El) m/z (%): 262 (100) [M+], 234 (38), 232 (13), 202 (11), 189 (13).IR (ATR) v (cm-1): 2969, 2832, 2359, 2340, 2203, 1739, 1661, 1587, 1569, 1507, 1481, 1458, 1442, 1427, 1361, 1316, 1293, 1250, 1229, 1216, 1177, 1162, 1141, 1119, 1070, 1059, 1043, 1015, 997, 953, 918, 868, 748, 737, 697, 687, 668, 630, 621, 616, 610.HRMS (El) for C17H10OS (262.0452): 262.0459.

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

Reference£º
Patent; Knochel, Paul; Mosrin, Marc; US2011/288296; (2011); A1;,
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20532-33-6, 5-Chlorobenzothiophene is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

a) Aluminium chloride (2.0g) was added in portions to a solution of 5-chlorobenzo[b]thiophene (1.7g) in benzene (50ml). After stirring for a further 1/2 hour, the reaction mixture was poured onto ice/dilute hydrochloric acid mixture and the organic layer separated. The aqueous was further extracted with diethyl ether. The combined extracts were dried and the solvent removed. The residue was stirred with hexane and the insoluble 5-chlorobenzo[b]thiophene dimer removed. Evaporation of the hexane gave a 50:50 mixture (as established by N.m.r.) of 5-chloro-2,3-dihydro-3-phenylbenzo[b]thiophene and 5-chloro-2,3-dihydro-2-phenylbenzo[b]thiophene as a colourless oil (1.3g).

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

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Patent; SHELL INTERNATIONALE RESEARCH, MAATSCHAPPIJ B.V.; EP526951; (1993); A1;,
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20532-34-7, Benzo[b]thiophen-5-ylmethanol is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

(5-Bromomethyl)benzo[b]thiophene (15b). To a stirred solution of benzo[b]thiophen-5-ylmethanol (14b) (100 mg, 0.61 mmol) in dry dichloromethane (15 mL) and under argon, PPh3 (290 mg, 1.09 mmol) and then CBr4 (240 mg, 0.73 mmol) were added. After stirring for 1 h, diethyl ether was added and the resulting precipitate was filtered and washed with diethyl ether. The solvents were removed under reduced pressure and the crude residue was purified by flash chromatography eluting with (10:90) diethyl ether/hexanes to afford bromide 15b (129 mg, 93%) as a white amorphous solid. 1H NMR (250 MHz, CDCl3) delta 7.86 (m, 2H, 2*ArH), 7.49 (d, 1H, J=5.5 Hz, ArH), 7.39 (d, 1H, J=8.7 Hz, ArH), 7.33 (d, 1H, J=5.5 Hz, ArH) and 4.66 (s, 2H, CH2O) ppm. 13 C NMR (63 MHz, CDCl3) delta 139.7 (C), 139.7 (C), 133.8 (C), 127.4 (CH), 125.2 (CH), 123.9 (CH), 123.7 (CH), 122.8 (CH) and 34.1 (CH2) ppm. MS (CI) m/z (%) 227 and 229 (MH+). HRMS calcd for C9H3S79Br (MH+): 226.9530; found, 226.9532.

20532-34-7 Benzo[b]thiophen-5-ylmethanol 2795446, abenzothiophene compound, is more and more widely used in various.

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Patent; UNIVERSIDADE DE SANTIAGO DE COMPOSTELA; US2011/313032; (2011); A1;,
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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.

A mixture of carboxylic acid in thionyl chloride (5 mL/mmol carboxylic acid) was stirred at 60 C for 2 hours. On completion, the solution was concentrated in vacuo to give the acid chloride, which was used directly without further purification. This material (1.1 eq) was added to a mixture of racemic amine (1 eq.) and triethylamine (2 eq.) in dichloromethane (3-5 mL/mmol racemic amine) at room temperature. The mixture was stirred at this temperature for 2 hours. On completion, the reaction was filtered, and the resulting filtrate was concentrated and purified by prep-HPLC to give racemic amide product. Following general procedure A, rac-1 was prepared from benzo[b]thiophene-2 -carboxylic acid and rac-A-104 (0.10 g, 0.65 mmol). The product was purified by prep-HPLC [Instrument: GX-C; Column: Phenomenex Gemini C 18 150×30 mm, particle size: 5 mupiiota; Mobile phase: 35-65% acetonitrile in H20 (add 0.5% NH3 H20, v/v)] to give rac-1 (0.15 g, 73% yield) as a white solid. LCMS : (ES+) m/z (M+H)+ = 315.1.

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

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

Benzo[b]thiophene-3-carbaldehyde (1.0 equiv.) in toluene (5 mL) was slowly added with constant stirring to a 50 mL three-necked round bottomf lask containing substituted 2-aminobenzothiazole (1.0 equiv.) and anhydrous toluene (10 mL). The reaction mixture was refluxed for 10 h and then cooled down to room temperature. The solvent was removed under reduced pressure, and the crude product was purified by recrystallization using N,N-dimethylethanamine/acetone/petroleum etherto yield pure imines 1a-1f.

The synthetic route of 5381-20-4 has been constantly updated, and we look forward to future research findings.

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Article; Zhang, Peiwei; Tang, Chenghao; Chen, Zhiwei; Wang, Bo; Wang, Xiang; Jin, Linhong; Yang, Song; Hu, Deyu; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 189; 4; (2014); p. 530 – 540;,
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10133-22-9, 5-(Bromomethyl)benzo[b]thiophene is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of 5-bromomethyl-benzo [b] thiophene (1. 55g, 6.8mmol, 2.4 eq) and 1,1- dimethylethyl 4-[(2-methylpropyl) amino] piperidine-1-carboxylate (0. 71g, 2. 8mmol, 1 eq) in acetonitrile (25ml) is added potassium carbonate (0.62g, 4.4mmol, 1.6eq). The mixture is heated to reflux for 16 hours. The solution is filtered and the solvent removed in vacuo. The resulting oil is purified on a 40g Redisep column using a gradient of 0-20% ethyl acetate/iso-hexane to give 1, 1-dimethylethyl 4-f [ (1-benzothienyl-5-yl) methyl]- (2- methylpropyl) amino}-piperidine-l-carboxylate as an oil (1.12 g, 100 %). mass spectrum (LCMS): m/z= 403.5 (M++1), Rt= 3.38 (6 min gradient) ; 1H NMR (300 MHz, CDC13) : 8= 7. 80-7. 60 (2 H, m), 7.37-7. 33 (1 H, m), 7.32-7. 26 (1 H, m), 7.25-7. 20 (1 H, m), 4.17- 3.94 (2 H, m), 3.65 (2 H, s), 2. 65-2. 36 (3 H, m), 2.24-2. 10 (2 H, d), 1.71-1. 28 (5 H, m), 1.38 (9 H, s), 0.88-0. 69 (6 H, d).

10133-22-9 5-(Bromomethyl)benzo[b]thiophene 11160498, abenzothiophene compound, is more and more widely used in various.

Reference£º
Patent; ELI LILLY AND COMPANY; WO2005/92885; (2005); A1;,
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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.

3-(Benzo[d]thiophen-3-yl)acrylic Acid Methyl Ester To a stirred suspension of lithium chloride (1.02 g; 24.1 mmol) in dry MeCN (180 mL) under nitrogen at room temperature was added drop-wise at 15 min intervals trimethyl phophonoacetate (4.39 g; 24.0 mmol) in dry MeCN (15 mL), DBU (3.05 g; 20.0 mmol) in dry MeCN and finally benzo[d]thiophen-3-carboxaldehyde (3.24 g; 20.0 mmol) in dry MeCN (30 mL). The reaction was allowed to stir at room temperature until completion, as determined by TLC. The reaction mixture was filtered and concentrated under reduced pressure. The resulting yellow oil was dissolved in DCM (60 mL) and washed with distilled water (3*20 mL) and saturated sodium chloride solution (3*20 mL). The organic layer was dried over sodium sulfate and concentrated under reduced pressure to give a red oil. Purification by column chromatography on silica gel using DCM as the eluent followed by recrystallization with hexanes gave a pale yellow crystalline solid (2.63 g; 60%): mp 63-65 C.; Rf0.68 (D); Rf0.45 (F); numax (KBr): 1708, 1281, 1159, 972 cm-1; m/z (EI): 218.0, 187.0, 159.1, 88.8; deltaH (CDCl3, 200 MHz): 3.84 (3 H, s), 6.54 (1 H, d, J=15.8), 7.41 (1 H, td, J=5.6 and 1.8), 7.47 (1 H, td, J=5.6 and 1.6), 7.76 (1 H, s), 7.88 (1 H, dq, J=7.0 and 2.2), 7.98 (1 H, dd, J=16.4 and 0.6), 8.02 (1 H, dq, J=5.0 and 1.4); deltaC (CDCl3, 101 MHz): 52.1, 118.6, 122.4, 123.3, 124.6, 125.4, 128.4, 131.9, 136.9, 137.4, 140.8, 167.9; m/z calculated for C12H10O2S: 218.0402 (M+), found 218.0401 (M+).

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

Reference£º
Patent; Queen’s University at Kingston; US2003/114441; (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.346592-74-3,7-Fluorobenzo[b]thiophene,as a common compound, the synthetic route is as follows.

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*50 mL). The extracts were concentrated and chromatographed (0 to 15% ethyl acetate in hexane) to yield 7-fluorobenzothiophene-3-carboxaldehyde (0.642 g).

346592-74-3 7-Fluorobenzo[b]thiophene 21866059, abenzothiophene compound, is more and more widely used in various.

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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.3541-37-5,Benzo[b]thiophene-2-carboxaldehyde,as a common compound, the synthetic route is as follows.

Step 1: A solution of benzo [b]thiophene-2-carbaldehyde (1.0 g, 6.17 mmol) and carbon tetrabromide (3.1 g, 9.25 mmol) in methylene chloride (50 mL) was cooled to 0C. A solution of triphenylphosphine (4.86 g, 18.3 mmol) in methylene chloride (20 mL) was added dropwise. After 1/2 hour the solution was placed on a plug of silica gel and eluted with 20% ethyl acetate: hexane. Concentration of the eluent resulted in the isolation of 1.3 g (67%) of 2- (2, 2-Dibromo-vinvl)-benzofblthiophene as a yellow oil, which was used as such in the next step.

The synthetic route of 3541-37-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; WYETH; WO2005/37807; (2005); A1;,
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