Heterocyclic Building Blocks-Benzothiophene

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

(d) 71.4 g (0.2 mol) of compound (IV), 122 g (1.2 mol, 6 ep) of triethylamine, and 860 ml of dichloromethane were placed in a flask and stirred at 20¡ãC for 1 hour.A mixture of 55 g (0.48 mol, 2.4 ep) of methanesulfonyl chloride and 50 ml of chloroform was added dropwise, and the addition was completed for 3 hours. After completion of the dropwise addition, the reaction was stirred at 30¡ãC for 6 hours.After the disappearance of the compound (IV) raw material, 28.3 g of compound (II) was added.(0.19 mol, 0.95 ep), the reaction was warmed at reflux and the reaction was carried out for 8 hours.After the reaction is completed, cool to room temperature and add 100mlX3 water to wash.The polyester and the organic phase were dried over anhydrous sodium sulfate, suction-filtered, and concentrated. Ethyl acetate (400 ml) was added to the residue, and the mixture was stirred and dissolved. The crystal was crystallized at room temperature for 3 hours, and then cooled to 0¡ã C. and crystallized for 3 hours.It was suction filtered, rinsed with cold ethyl acetate and sucked dry to give a white solid: crude ipripiprazole (I). The crude product was dissolved in 400 ml of anhydrous ethanol, and hydrochloric acid was added dropwise at 20¡ã C., adjusting the pH to 2 and stirring for 1 hour. After cooling to 0¡ãC, the crystals were stirred for 4 hours. Filtering, rinsing with cold ethanol, and draining. The obtained hydrochloride was dissolved in 320 ml of purified water, and 10percent sodium carbonate solution was added dropwise at 20¡ãC. The pH was adjusted to 9. The addition was complete, and the mixture was stirred for 30 minutes. The retest pH was 9 and the mixture was stirred for 30 minutes. 100ml of water was rinsed, drained, and dried white solid 70g, yield 80.5percent.

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

Reference£º
Patent; Zhejiang Liaoyuan Pharmaceutical Co., Ltd.; Song Zhigang; Yang Minhua; Cui Jianfeng; Chen Weijun; (16 pag.)CN106831739; (2017); A;,
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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.

i) 4-Benzo[b]thiophen-7-yl-pyridine This compound was prepared in analogy to the procedure described in Example 16i) starting from 7-bromo-benzo[b]thiophene (Focus synthesis, CAS:1423-61-6) using 4-pyridineboronic acid as reagent to obtain 4-benzo[b]thiophen-7-yl-pyridine as a grey solid. MS (ISP): m/e 212.1 (M+H)+

The synthetic route of 1423-61-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Hebeisen, Paul; Kitas, Eric A.; Minder, Rudolf E.; Mohr, Peter; Wessel, Hans Peter; US2009/143448; (2009); 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.

Example 52-(benzo[b]thiophen-3-yl)-/V,/V-dibuty^carboxamide To a stirred solution of 5-amino-/V,/V-dibutyl-6-((3-(piperidin-1 -yl)propyl)amino)picolinamide (54 mg, 0.14 mmol) in nitrobenzene (2 mL) was added benzothiophene-3-carboxaldehyde (30 mg, 0.18 mmol). The mixture was stirred at 100 C for 12 hours then purified by reverse-phase preparative HPLC (Solvent A: MeOH:H20:TFA (5:95:0.05). Solvent B: MeOH:H20:TFA (95:5:0.05). Gradient 30 to 100% B in 17 min. Column: Zorbax SB-C18 PrepHT, 5 microns, 21.2 x 100 mm. Wavelength 220 nm) to afford the title compound (42 mg, 40%). Analytical HPLC: ret. time= 2.01 min; LCMS m/z 532.3 (M + H)+, ret. time= 3.43 min. NMR (600 MHz, MeOH-d4) delta ppm : 8.31 (1 H, s), 8.28 (1 H, d), 8.09 (1 H, m), 8.04 (1 H, m), 7.59 (1 H, d), 7.53 (1 H, m), 4.57 (2H, t), 3.59 (2H, m), 3.39 (2H, m), 3.34 (1 H, m), 3.00 (2H, m), 2.75 (2H, m), 2.22 (2H, m), 1.85 (2H, m), 1.75 (2H, m), 1.68-1.56 (4H, m), 1.51 -1.36 (3H, m), 1.19 (2H, m), 1.04 (3H, t), 0.82 (3H, t).

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

Reference£º
Patent; UNIVERSITE DE MONTREAL; RUEL, Rejean; CHANTIGNY, Yves; MARINIER, Anne; RENE, Patricia; BOUVIER, Michel; WO2012/3576; (2012); 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.

General procedure: To a suspension of methyltriphenylphosphonium bromide (1.2 equiv.) in dry THF (2 mL per mmol) wasadded n-BuLi (1.6 M in hexane, 1.2 equiv.) dropwise at -78 C. The resulting solution was then allowedto warm up to 0 C over a period of 1 h. The solution was then cooled to -30 C and treated with amixture of the corresponding aldehyde (1.00 equiv.) with stirring at room temperature (rt) until thestarting material had disappeared, as evidenced by TLC. The reaction mixture was quenched by addingH2O (10 mL per mmol), the phases were separated, the aqueous phase was extracted with Et2O, and thecombined organic layers were dried over MgSO4 and concentrated under reduced pressure. The productwas obtained by column chromatography.

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

Reference£º
Article; Pan, Jian; Morimoto, Tsumoru; Kobayashi, Hideyuki; Tanimoto, Hiroki; Kakiuchi, Kiyomi; Heterocycles; vol. 98; 4; (2019); p. 519 – 533;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.95-15-8,Thianaphthene,as a common compound, the synthetic route is as follows.

n-Butyllithium (1.6 M solution in hexanes; 74.6 ml) was added dropwise under nitrogen at 0¡ã C. to a stirred solution of benzo[b]thiophene (25.0 g) in ether (350 ml), then the mixture cooled to -70¡ã C. and a solution of N-methoxy-N-methylacetamide (19.21 g) in ether (100 ml) was added dropwise. The mixture was stirred at ambient temperature for 18 hours, then it was poured into saturated aqueous ammonium chloride solution (400 ml). The organic phase was separated, washed with water (300 ml) and saturated aqueous sodium chloride solution (300 ml), dried (Na2SO4) and the solvents were removed in vacuo. The residue was triturated with petroleum ether (b.p. 60-80¡ã C.) (50 ml) and the resulting solid was collected by filtration and dried in vacuo to give 1-(benzo[b]thiophen-2-yl)ethan-1-one (18.7 g) as a brown solid, m.p. 78-81¡ã C.

The synthetic route of 95-15-8 has been constantly updated, and we look forward to future research findings.

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.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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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.

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.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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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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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.

Reference£º
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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