Category: benzothiophene

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.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.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.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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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.130-03-0,Benzo[b]thiophen-3(2H)-one,as a common compound, the synthetic route is as follows.

General procedure: To a stirred mixture of ketone 1a or 1b (3 mmol) and diarylpropargylic alcohols 2a-e (3 ml) in acetonitrile (3 ml) the corresponding catalyst (Table 1) was added and the reaction mixture was refluxed under argon for 1 h. After cooling, the solvent was distilled off in vacuo. The residue was purified by recrystallization from the corresponding solvent or by chromatography on silica gel using the light petroleum/ethyl acetate (8:1) system as an eluent.

130-03-0 Benzo[b]thiophen-3(2H)-one 10986413, abenzothiophene compound, is more and more widely used in various.

Reference£º
Article; Shirinian, Valerii Z.; Zavarzin, Igor V.; Leonova, Evgeniya S.; Markosyan, Ashot I.; Mendeleev Communications; vol. 25; 4; (2015); p. 262 – 263;,
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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.

To a solution of Lambda/1-((3S)-4-{[(2-chloro-4-fluorophenyl)sulfonyl]amino}-3- hydroxybutyl)-L-leucinamide (67 mg, 0.15 mmol) in dichloromethane (2 mL) was added benzothiophene carboxylic acid (29 mg, 0.18 mmol) and HOOBt (2.0 mg, 0.01 mmol) at rt. After cooling the reaction mixture in an ice-bath, NMM (0.45 mmol) and EDCHCI (34 mg, 0.18 mmol) were added. After stirring overnight at rt, the reaction mixture was washed with 10 % (w/w) aqueous citric acid solution (1 mL) and brine. The organic solution was dried over MgSO4, concentrated under reduced pressure, and then purified by silica gel column chromatography (30% – 90% EtOAc/Hex) to give the title compound (0.06Og, 71%, white solid); LCMS: [MH]+= 570.2.

The synthetic route of 6314-28-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; SMITHKLINE BEECHAM CORPORATION; WO2007/30761; (2007); A2;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1127-35-1,Benzo[b]thiophene-3(2H)-one 1,1-Dioxide,as a common compound, the synthetic route is as follows.

A mixture of benzo[b]thiophen-3(2H)-one-1,1-dioxide(1b)(0.91 g, 5.0 mmol), hexamethylenetetramine (1.40 g, 10.0 mmol) and ammoniumacetate (0.95 g, 12.3 mmol) in a mixture of acetic acid (20 mL) with triuoroacetic acid (5 mL) was heated under reflux for 1 h with stirring. Aftercooling a white precipitate was ltered off and crystallised from acetic acidgiving 2b (0.74 g, 75%) as a whitepowder, mp 245C. 1H NMR (CDCl3, 400 MHz): 2.70 (s, 2H),4.02 and 4.59 (AB-syst, 2J=20.2Hz, 4H), 7.70 (d, 3J=7.2Hz, 2H), 7.78 (t, 3J=7.2Hz, 2H), 7.80 (t, 3J=7.2Hz, 2H), 7.80 (d, 3J=7.2Hz, 2H). 13C NMR (CDCl3, 100.56 MHz): 21.1, 55.9, 59.8,122.0, 124.4, 133.2, 133.7, 134.6, 141.6, 159.5. IR (film) 1318, 1464, 1664 cm-1. MS (+ESI) m/z (relative intensity) 399 ([M+H]+100). Anal. Calcd. for C19H14N2O4S2¡Á CH3COOH: C, 55.01; H, 3.95; N, 6.11. Found: C, 55.36; H, 3.67; N,6.20. The 1H NMR spectrum was in accordance with described in the literature.

1127-35-1 Benzo[b]thiophene-3(2H)-one 1,1-Dioxide 70780, abenzothiophene compound, is more and more widely used in various.

Reference£º
Article; Cekavicus, Brigita; Vigante, Brigita; Rucins, Martins; Plotniece, Aiva; Pajuste, Karlis; Petrova, Marina; Belyakov, Sergey; Duburs, Gunars; Sobolev, Arkadij; Tetrahedron Letters; vol. 55; 33; (2014); p. 4601 – 4604;,
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1196-19-6, 3-(Bromomethyl)benzo[b]thiophene is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 1 Production of ((benzothiophene-3-yl)methyl)(4-methoxy-2-nitrophenyl)amine 740 mg (2.8 mmol) of 4-methoxy-2-nitrotrifluoroanilide were dissolved in 5 ml of dimethylformamide followed by the sequential addition of 503 mg (3.64 mmol) of potassium carbonate and 773 mg (3.4 mmol) of 3-bromomethylbenzothiophene and heating to 100 C. After 12 hours, 5 ml of 5 M aqueous sodium hydroxide solution were added and refluxed, as is, for 1 hour. After 15 minutes, the solution was cooled to room temperature followed by the addition of 10 ml of water and extraction with chloroform. After washing the organic phase twice with 25 ml of saturated brine and drying with magnesium sulfate, it was concentrated and dried under reduced pressure. The residue was then purified by silica gel column chromatography (hexane:ethyl acetate=60:1) to obtain 400 mg of ((benzothiophene-3-yl)methyl)(4-methoxy-2-nitrophenyl)amine in the form of an orange powder (yield: 44%).

1196-19-6 3-(Bromomethyl)benzo[b]thiophene 11264641, abenzothiophene compound, is more and more widely used in various.

Reference£º
Patent; TEIJIN LIMITED; US2005/267148; (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.3541-37-5,Benzo[b]thiophene-2-carboxaldehyde,as a common compound, the synthetic route is as follows.

General procedure: Representative Procedure for Mukaiyama Aldol Reactions of Me2C C(OMe)OSiMe3 with Aryl Aldehydes Catalyzed by 1-5. To an oven-dried 10-mL vial equipped with a magnetic stirring bar and a septum was added acetonitrile (5 mL), 1 (0.03 mmol), and aldehyde (1.0 mmol). The mixture was stirred for 30 min at room temperature, followed by addition of Me2C C(OMe)OSiMe3 (1.2 mmol). When the reaction was judged to be complete by TLC, the reaction was quenched by adding 2 N HCl (3 mL) solution followed by stirring the reaction mixture for an additional 3 h at room temperature. The reaction mixture was extracted with methylene chloride and dried over Na2SO4, the solution was filtered and dried on a rotavap apparatus, and then the crude product was purified by silica gel column chromatography (EtOAc:hexanes = 1:9).

As the paragraph descriping shows that 3541-37-5 is playing an increasingly important role.

Reference£º
Article; Kim, So Han; Yoon, Sungwoo; Kim, Youngjo; Verkade, John G.; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 189; (2014); p. 1193 – 1206;,
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