Category: 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.

6314-28-9, General procedure: The DCC (1.2 equiv) was added to the solution of caudatin(0.2 mmol), DMAP (0.2 equiv), and appropriate carboxylic acid (1.2 equiv) in anhydrous CH2Cl2 (8 mL) at 0 C.The resulting mixture was stirred at room temperature until the starting material was not observed by TLC. The reaction mixture was filtered, and the residue was washed with CH2Cl2 (210 mL). Then, the CH2Cl2 solution was washed with 5% HCl (330 mL), saturated NaHCO3 (330 mL) and saturated NaCl (330 mL), respectively. Subsequently, the organic layer was dried by Na2SO4 and concentrated to dryness under reduced pressure. At last, the residue was purified by column chromatography over the silica gel with petroleum ether/acetone (60:40 – 95:5) to yield the pure target compounds.

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

Reference£º
Article; Wang, Li-Jun; Chen, Hao; Ma, Yun-Bao; Huang, Xiao-Yan; Geng, Chang-An; Zhang, Xue-Mei; Chen, Ji-Jun; Medicinal Chemistry; vol. 11; 2; (2015); p. 165 – 179;,
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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.

5381-20-4, General procedure: Amixture of the heterocyclic salt I1-I16 (2.5 mmol), aldehyde (7.5 mmol, 3 molar equiv, unlessotherwise stated) and piperidine (0.50 mL, 5 mmol, 2 molar equiv) in EtOH (25 mL) was heatedunder reflux for 2.5 h. After cooling to room temperature, the precipitated solid was collectedby filtration, washed with EtOH (2 ¡Á 5 mL) and Et2O (2 ¡Á 5 mL) and dried. The crude iodidesalt was either purified through a recrystallization from a suitable solvent (as indicated below)to give an analytically pure sample, or subjected to anion exchange to bromide or chloride, asdescribed below. Procedure for anion exchange: Ion-exchange resin (Amberlite IRA-402, Cl- form, or AmberliteIRA-400, Br- form, about 20 mmol equiv) was thoroughly rinsed with a mixture of MeCN andMeOH (1:1, v/v) and charged into a short glass column. The dye (iodide salt) was dissolvedin a minimal amount of a mixture of MeCN and MeOH (1:1, v/v) and loaded in the column. Theproduct was then eluted with the same solvent mixture (about 50 mL). The solvents wereremoved in vacuo and the residue was recrystallized from a suitable solvent (as indicatedbelow), to give an analytically pure dye.

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

Reference£º
Article; Xie, Xiao; Zuffo, Michela; Teulade-Fichou, Marie-Paule; Granzhan, Anton; Beilstein Journal of Organic Chemistry; vol. 15; (2019); p. 1872 – 1889;,
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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,95-15-8

EXAMPLE 1 N-(1-trans-(2-(benzo[b]thien-2-yl)cyclopropyl)ethyl)-N-hydroxyurea STR18 To a solution of benzo[b]thiophene (11.49 g, 85.6 mmol) in 300 mls THF at -78 C., was added n-butyllithium (36.0 mls of a 2.5 M solution in hexanes, B9.9 mmol) dropwise and the mixture was stirred for 30 mins at -78 C. N,N,-Dimethylformamide (6.57 g, 89.9 mmol) was added and the reaction was allowed to stir for 30 min. The cooling bath was then withdrawn and the reaction was allowed to warm to room temperature. It was then diluted with saturated aqueous NH4 Cl (250 mL) and extracted with ethylacetate (3*250 mL). The organics were combined, dried with MgSO4 and concentrated. The resulting residue was taken up in 20 mL ethanol and saturated aqueous NaHSO3 (200 mL) was added. The resulting precipitate was collected and washed with ether. It was then dissolved in saturated aqueous Na2 CO3 (200 mL) and the resulting aqueous solution was extracted with ethylacetate (3*200 mL). The organics were combined, dried with MgSO4 and concentrated to afford 13.63 g (98%) of benzo[b]thien-2-ylcarboxaldehyde.

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

Reference£º
Patent; Abbott Laboratories; US5037853; (1991); A;,
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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

6314-28-9, To a solution of benzo[t]thiophene-2-carboxylic acid (274 mg, 1.54 mmol) and 4- (tert-butyl)thiazol-2-amine (200 mg, 1.28 mmol) in DMF (0.84 mL) was added HATU (585 mg, 1.54 mmol) followed by DIEA (791 uL, 4.90 mmol). The mixture was heated to 80 C for 3 h then cooled to ambient temperature, diluted with ethyl acetate (5 mL) and brine (5 mL), and extracted with ethyl acetate (1X5 mL). The organics were combined, washed with brine (2X5 mL), dried with sodium sulfate, filtered, and concentrated. Flash chromatography (0-60% hexanes/ethyl acetate) provided N-(4-tert-butyl-1 ,3-thiazol-2-yl)-1 -benzothiophene-2- carboxamide (397 mg, 98% yield) as an off-white solid. (A145) H NMR (400 MHz, DMSO-d6) delta 12.92 (s, 1 H), 8.63 (s, 1 H), 8.38 – 7.81 (m, 2H), 7.71 – 7.29 (m, 2H), 6.85 (s, 1 H), 3.33 (s, 3H), 1.31 (s, 9H). LCMS for C16H16N202S, found 317 [M+H]+.

As the paragraph descriping shows that 6314-28-9 is playing an increasingly important role.

Reference£º
Patent; KEZAR LIFE SCIENCES; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; MCMINN, Dustin; JOHNSON, Henry; TAUNTON, John, William; CARRASCO, Yazmin, Paulina; SHARP, Phillip, Patrick; (156 pag.)WO2019/46668; (2019); A1;,
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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

As the paragraph descriping shows that 130-03-0 is playing an increasingly important role.

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.1423-61-6,7-Bromobenzo[b]thiophene,as a common compound, the synthetic route is as follows.,1423-61-6

Under Ar atmosphere, to a mixture of 7-bromo-benzo[b]thiophene (40 g, 0.19 mol) and Zn(CN)2 (16 g, 0.132 mol) were added Pd(PPh3)4 (10 g) and DMF (800 mL) and the mixture was stirred at 90 0C -100 0C for 3 h. The reaction solution was cooled to room temperature (30 0C) and filtered. The filtrate was concentrated under reduced pressure. The residue was taken up with EtOAc (1000 mL) and saturated aq. NaHCO3 (500 mL) and then filtered. The filtrate layers were separated. The organic layer was washed with brine, dried over Na2SO4 and concentrated to give a crude product, which was purified by column chromatography (silica, elute; PE to EtOAc_PE=l:30) to afford the title compound (24 g, 80 %) as a white solid.

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

Reference£º
Patent; TARGEGEN INC.; WO2009/49028; (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.17402-83-4,Benzo[b]thiophen-4-amine,as a common compound, the synthetic route is as follows.

l-Benzothiophen-4-amine (3.3g, 0.022 mol) was added to a stirred solution of ((4-((2-oxo-l,2- dihydroquinolin-7-yl)oxy)butyl)azanediyl)bis(ethane-2,l-diyl)dimethanesulfonate (10 g, 0.021 mol) in toluene (90 ml) at 25-35¡ãC. Then potassium tertiary butoxide (7.1g, 0.063 mol) was added to the reaction mixture slowly. Completion of reaction was confirmed using thin layer chromatography (TLC). After completion of the reaction, water (50 ml) was added to reaction mixture and extracted. The organic phase was separated and evaporated under vacuum to obtain residue. Methanol (50 ml) was added to the residue and stirred for 2 h at 25-35¡ãC. The solid obtained was filtered, washed with methanol (20 ml) then dried to obtain the title product as off white solid (10 g)., 17402-83-4

As the paragraph descriping shows that 17402-83-4 is playing an increasingly important role.

Reference£º
Patent; AMNEAL PHARMACEUTICALS COMPANY GMBH; JAGTAP, Bhushan Nimba; BADGUJAR, Narendra Dattatray; MAHETA, Abhay Subodhbhai; BUTANI, Pankaj Chhaganbhai; AJUDIA, Paragkumar Vrujlal; KOILPILLAI, Joseph Prabahar; AGARWAL, Virendra Kumar; HEDAPARA, Kalpesh Ratilal; (96 pag.)WO2018/172463; (2018); 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

Preparation III 3-bromo-5-chlorobenzothiophene To a solution of 0.30 gm (1.77 mMol) 5-chlorobenzothiophene 1.0 mL acetic acid was added a solution of 0.31 gm (1.95 mMol) bromine in 1.0 mL acetic acid under a nitrogen atmosphere. The reaction was heated to 50C for 4 hours at which time the volatiles were removed under reduced pressure. The residue was partitioned between dichloromethane and aqueous sodium bicarbonate. The phases were separated and the organics were washed with saturated aqueous sodium chloride, dried over sodium sulfate and concentrated under reduced pressure to give 0.335 gm (76%) of the title compound as a tan solid. m.p.= 85-86C MS(FD): m/e=249 (M+2) EA: Calculated for: C8H4BrClS: Theory: C, 38.82; H, 1.63. Found: C, 39.12; H, 1.72.

20532-33-6, The synthetic route of 20532-33-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ELI LILLY AND COMPANY; EP812826; (1997); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.4923-87-9,5-Bromobenzothiophene,as a common compound, the synthetic route is as follows.,4923-87-9

General procedure: A 10-mL Schlenk tube was charged with Pd(OAc)2 (1.7 mg, 0.0075 mmol, 3.0 mol %), SPhos (6.2 mg, 0.015 mmol, 6.0 mol %), Na2CO3 (53.0 mg, 0.50 mmol, 2.0 equiv), potassium 6-fluoropyridine-2-trifluoroborate (101.5 mg, 0.50 mmol, 2.0 equiv) and heteroaryl halides (0.25 mmol, 1.0 equiv), followed by the addition of ethanol (2.0 ml). The reaction was carried out at 85 C for 16 h under the protection of nitrogen gas. Then, the reaction mixture was allowed to cool down to room temperature and the reaction solution was filtered through a thin pad of silica gel (eluting with ethyl acetate) and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel flash chromatography to produce the desired products (ethyl acetate/hexane=1:2-1:80).

4923-87-9 5-Bromobenzothiophene 2776578, abenzothiophene compound, is more and more widely used in various fields.

Reference£º
Article; Ren, Wei; Li, Jingya; Zou, Dapeng; Wu, Yangjie; Wu, Yusheng; Tetrahedron; vol. 68; 5; (2012); p. 1351 – 1358;,
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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.

5381-20-4, Synthesis of 2-(3-(trifluoromethyl)phenyl)benzo[b]thiophene-3-carbaldehyde (29a): 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. Pd(dba)2 (17 mg, 3 mol %) and P(o-furyl)3 (14 mg, 6 mol %) dissolved in THF (2 mL), and mixed with 3-iodobenzomethyltrifluoride (354 mg, 1.3 mmol, 1.3 equiv) were then transferred via cannula to the reaction mixture. The resulting mixture was stirred for 1 h at 25 C. The reaction mixture was then quenched 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, 1:3) furnished compound 29a (281 mg, 92%) as a colourless solid. m.p.: 102.8 – 104.2 C.1H-NMR (400 MHz, CDCl3) delta: 10.02 (s, 1 H), 8.79 (m, 1 H), 7.45-7.87 (m, 7 H).13C-NMR (100 MHz, CDCl3) delta: 185.9, 158.0, 138.0, 136.8, 133.7, 132.4, 131.5 (q, J (C-F)=33.0 Hz), 130.7, 129.5, 127.0 (q, J (C-F)=3.8 Hz), 126.6 (q, J (C-F)=3.8 Hz), 126.5, 126.2, 123.5 (q, J (C-F)=272.5 Hz), 121.7.MS (70 eV, El) m/z (%): 306 (97) [M+], 305 (100), 278 (12), 257 (13), 237 (28), 233 (18), 208 (29), 160 (13), 44 (40).IR (ATR) v (cm-1): 3068, 2866, 2359, 1926, 1745, 1669, 1590, 1520, 1483, 1459, 1438, 1421, 1392, 1351, 1325, 1310, 1288, 1265, 1217, 1178, 1156, 1118, 1097, 1092, 1073, 1051, 1018, 1000, 994, 966, 947, 933, 907, 868, 863, 812, 773, 754, 733, 703, 679, 653, 641, 633, 620, 608, 603.HRMS (El) for C16H9F3OS (306.0326): 306.0326.

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

Reference£º
Patent; Knochel, Paul; Mosrin, Marc; US2011/288296; (2011); A1;,
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