Heterocyclic Building Blocks-Benzothiophene

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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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.

Reference£º
Patent; UNIVERSIDADE DE SANTIAGO DE COMPOSTELA; US2011/313032; (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.

Reference£º
Patent; SHELL INTERNATIONALE RESEARCH, MAATSCHAPPIJ B.V.; EP526951; (1993); 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

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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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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6314-28-9, Benzo[b]thiophene-2-carboxylic acid is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

REFERENCE EXAMPLE 1971-[(2-Benzothienylcarbonyl)amino]cyclohexanecarboxylic acid phenylmethyl ester Under ice-cooling, 5.9 g (31 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was added to a solution of 5 g (28 mmol) of 2-benzothiophenecarboxylic acid, 6.5 g (28 mmol) of 1-aminocyclohexanecarboxylic acid phenylmethyl ester and 4.5 g (29 mmol) of 1-hydroxybenzotriazole in methylene chloride. After the mixture was stirred at room temperature overnight, the reaction solvent was distilled off under reduced pressure. Water was added to the residue, and the mixture was extracted with ethyl acetate twice. The obtained organic layer was washed with a 10% aqueous potassium hydrogensulfate solution, a saturated aqueous sodium hydrogencarbonate solution and then saturated brine, and it was dried with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, diethyl ether was added to the obtained residue, and the mixture was stirred overnight. The crystal was collected by filtration and heated/dried under reduced pressure to obtain 10 g (91%) of the title compound.1H-NMR (CDCl3, delta): 1.25-1.78 (6H, m), 1.93-2.05 (2H, m) 2.12-2.25 (2H, m), 5.18 (2H, s), 6.24 (1H, s), 7.20-7.38 (5H, m), 7.38-7.51 (2H, m), 7.77 (1H, s), 7.80-7.91 (2H, m)

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

Reference£º
Patent; SEIKAGAKU CORPORATION; US2009/137799; (2009); A1;,
Benzothiophene – Wikipedia
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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.

1 g of 4-bromophenylacetonitrile (5.1 mmol) and 825 mg ofbenzo[b]thiophene-2-carboxaldehyde (5.1 mmol) were dissolvedin dry MeOH (30 mL) and stirred at 0 C for 5 min 380 mg of odium methoxide (7.1 mmol) were added in small portions, and themixture was stirred for 15 min at 0 C and then for 4 h at roomtemperature. The resulting precipitate was collected using a sinteredglass filter, washed with 10 mL of MeOH, then with water anddried to give 1.56 g of the alpha,beta-unsaturated nitrile 7 as a yellow solid(90%); Rf 0.36 (cyclohexane/EtOAc, 90:10); m.p 160-162 C ; 1HNMR (300 MHz, CDCl3): d (ppm): 7.37-7.45 (m, 2H), 7.52-7.60 (m,4H), 7.69 (s, 1H, Hvinyl), 7.82-7.87 (m, 3H); 13C NMR (75 MHz,CDCl3): delta(ppm): 109.68 (C), 117.35 (CN), 122.43 (CH), 123.58 (C),124.65 (CH), 125.12 (CH), 126.67 (CH), 127.33 (2CH), 130.01 (CH),132.31 (2CH) 132.86 (C), 134.86 (CH), 137.37 (C), 138.69 (C), 141.28(C); HRMS (MALDI-TOF) Calcd for (C17H10BrNS): [M]+: 338.9717.Found: 338.9711.

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

Reference£º
Article; Hafedh, Nesrine; Aloui, Faouzi; Raouafi, Sondes; Journal of Molecular Structure; vol. 1165; (2018); p. 126 – 131;,
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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

3-Benzo[b]thiophen-3-yl-3-hydroxy-propionitrile. (0168) To a stirring solution of diisopropylamine (0.93 mL, 6.58 mmol) in tetrahydrofuran (8 mL) at -78 C. under nitrogen was added a solution of n-butyllithium (2.75 mL, 6.88 mmol, 2.5 M in hexane). After the addition was complete, the mixture was stirred at -78 C. for 10 minutes and removed cooling bath for 5 minutes. The mixture was cooled back to -78 C., acetonitrile (0.31 mL, 5.98 mmol) was added and the reaction mixture was then stirred at -78 C. for 30 minutes. Benzo[b]thiophene-3-carbaldehyde (1 g, 5.98 mmol) in tetrahydrofuran (4 mL) was added and the resulting solution was allowed to warm to ambient temperature. After 18 hours at ambient temperature, saturated aqueous ammonium chloride (5 mL) was added to the reaction mixture and it was concentrated at reduced pressure. The resulting crude product was diluted with ethyl acetate (20 mL), washed with water (10 mL) followed by saturated aqueous sodium chloride (10 mL). The organic layer was concentrated and purified by column chromatography (80 g silica gel cartridge) eluting with ethyl acetate/hexane (30%-50%) to give the product as a light yellow oil (1.2 g, 99%).

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

Reference£º
Patent; Fox Chase Chemical Diversity Center, Inc.; Advanced Neural Dynamics, Inc.; Smith, Garry Robert; Brenneman, Douglas E.; Reitz, Allen B.; Zhang, Yan; Du, Yanming; US8609849; (2013); B1;,
Benzothiophene – Wikipedia
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.146137-92-0,Methyl 5-(trifluoromethyl)benzo[b]thiophene-2-carboxylate,as a common compound, the synthetic route is as follows.

A mixture of 300 mg of methyl 5- ( trifluoromethyl ) benzo [ b] thiophene-2-carboxylate, 66 mg of lithium hydroxide monohydrate, 2 ml of water and 6 ml of methanol was stirred at 75C for 1 hour. The reaction mixture was cooled to room temperature, and then concentrated under reduced pressure. To the residue was added water, and then washed with tert-butyl methyl ether 3 times. To the aqueous layer was added concentrated hydrochloric acid, and then extracted with tert- butyl methyl ether 3 times. The combined organic layer was washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, and then concentrated under reduced pressure to obtain 280 mg of 5-(trifluoromethyl) benzo[ b] thiophene-2-carboxylic acid (the present compound 1) .[ The present compound 1]1H-NMR(CDC13 ) delta: 8.24(s, 1H) , 8.21(s, 1H) , 8.02 (d, J=8.7Hz, 1H) , 7.72 (d, J=8.7Hz, 1H)

As the paragraph descriping shows that 146137-92-0 is playing an increasingly important role.

Reference£º
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; MUKUMOTO, Fujio; TAMAKI, Hiroaki; IWAKOSHI, Mitsuhiko; KUSAKA, Shintaro; WO2012/153861; (2012); A1;,
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95-15-8, Thianaphthene is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: A dried and argon-flushed Schlenk tube is charged with the correspondingsubstrate (1.0 mmol, 1.0 equiv) and dissolved in THF(1.0 mL). TMP2Mn¡¤2MgCl2¡¤4LiCl (1.5 mL, 0.6 mmol, 0.6 equiv,0.40 M solution in THF) is added dropwise at the given temperatureand stirred until a reaction aliquot quenched withiodine in THF showed full consumption of the starting material.Then, the reaction mixture is cooled to the given temperature,and chloranil (1.0 mmol, 1.0 equiv) dissolved in THF (4.0 mL) isadded dropwise. The reaction is stirred for 0.5 h and is thenquenched with sat. aq NH4Cl solution and extracted with CH2Cl2(3 ¡Á 25 mL). The crude product is purified by column chromatographyon silica to yield the corresponding title compound

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

Reference£º
Article; Haas, Diana; Hammann, Jeffrey M.; Moyeux, Alban; Cahiez, Gerard; Knochel, Paul; Synlett; vol. 26; 11; (2015); p. 1515 – 1519;,
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