Heterocyclic Building Blocks-Benzothiophene

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

In a 300 mL round bottomed flask, 5-bromobenzo[b]thiophene (5.6 g, 26 mmol) and dichloro(diphenylphosphinopropyne)nickel (0.54 g, 1.0 mol, 4 mol %) were dissolved in anhydrous THF (50 mL). A 1.0M octylmagnesium bromide solution (31 mL, 31 mmol, 1.2 eq.) was added thereto, and the mixture solution was stirred at room temperature for one day. After the completion of the reaction, hydrochloric acid and toluene were added, and an organic phase was extracted with toluene, and dried over sodium sulfate. The resulting crude product was purified by column chromatography, whereby intermediate C1 was obtained (4.1 g, yield 62%).

As the paragraph descriping shows that 4923-87-9 is playing an increasingly important role.

Reference£º
Patent; IDEMITSU KOSAN CO., LTD.; US2012/273768; (2012); 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,5381-20-4

General procedure: To a stirred solution of the triphenylphosphonium salt (0.005 mol) and the corresponding aldehyde (0.011 mol) in absolute ethanol (100 mL) the solution of sodium ethoxide (0.253 g, 0.011 mol in 15 mL of absolute ethanol) was added dropwise. The reaction was complete within 3-4 h (usually was left to stand overnight). After removal of the solvent, the residue was worked up with water and benzene. The benzene extracts were dried (anhydrous MgSO4) and concentrated. The crude reaction mixture was purified and the isomers of products 7 and 8 were separated by repeated column chromatography on silica gel using petroleum ether as the eluent. The first fractions yielded cis,cis-, cis,trans- and the last fractions trans,trans-isomers. The data of the new compounds 7a-c and 8a,b are given below. All isomers of 2,2′-(1,2-phenylenedivinylene)dithiophene (7a), 3,3′-(1,2-phenylenedivinylene)dithiophene (8a) and 3,3′-(1,2-phenylenedivinylene)dibenzo[b]thiophene (8b) are separated and described by spectroscopic methods whereas in the case of 7b and 7c only trans,trans-isomers are isolated.

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

Reference£º
Article; Vuk, Dragana; Marini?, ?eljko; Mol?anov, Kre?imir; Koji?-Prodi?, Biserka; ?indler-Kulyk, Marija; Tetrahedron; vol. 68; 34; (2012); p. 6873 – 6880;,
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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: A mixture of aromatic aldehydes 1a-u (0.73 mmol,0.0892 mL), iodine (10 mol%, 18.5 mg), ethyl pyruvate 2(0.73 mmol, 0.0817 mL) was heated at 80 C for 2 h. Aftercompletion of the reaction (TLC), the reaction mixture was washed with saturated sodium thiosulfate solution (5 mL)to destroy iodine, and after the addition of diethyl ether(20 mL), both aqueous and organic phases were separated.The organic layer was washed with saturated aqueous NaCland filtered over MgSO4.The filtrate was concentrated underreduced pressure. The filtrate was loaded on to silica gel columnchromatography using hexane-EtOAc (10:2 and 10:1)as eluent to obtain pure products 3a-u. Spectroscopic datafor a representative compounds are given below.

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

Reference£º
Article; Pommidi, Anil; Shaik, Asha Begum; Chatterjee, Anindita; Somarapu, Vijaya Laxmi; Journal of the Iranian Chemical Society; (2020);,
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1127-35-1, Benzo[b]thiophene-3(2H)-one 1,1-Dioxide is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,1127-35-1

To a solution of 3,4,5-trimethoxybenzaldehyde (1) (0.392 g, 2.00 mmol) in acetic acid (10 mL) piperidine (10% mol equiv) and benzo[b]thiophen-3(2H)one 1,1-dioxide (2) (0.364 g, 2.00 mmol) were added. The reaction mixture was stirred under reflux for 30 min. After cooling the precipitate was filtered off and crystallised from a mixture of acetic acid and methanol giving 3c (0.505 g, 70%) as yellow crystals, Rf=0.58 (50% EtOAc/hexane), mp 203-205 C. 1H NMR (CDCl3) delta: 3.95 (s, 6H), 3.99 (s, 3H), 7.43 (s, 2H), 7.83 (dd, J=7.7, 7.7 Hz, 1H), 7.91 (s, 1H), 7.92 (dd, J=7.7, 7.7 Hz, 1H), 8.03 (d, J=7.7 Hz, 1H), 8.10 (d, J=7.7 Hz, 1H). 13C NMR (CDCl3) delta: 56.4, 61.2, 111.2, 121.4, 124.8, 125.5, 129.5, 132.4, 134.2, 136.5, 143.5, 144.2, 145.4, 153.3, 178.8. IR (film) nu: 1506, 1578, 1702 cm-1. MS (+ESI) m/z (relative intensity) 361 ([M+H]+, 100). Anal. Calcd for C18H16O6S: C 59.99; H 4.48; found: C 59.64; H 4.56.

The synthetic route of 1127-35-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Cekavicus, Brigita; Vigante, Brigita; Rucins, Martins; Birkmane, Kintija; Petrova, Marina; Belyakov, Sergey; Zuka, Liga; Plotniece, Aiva; Pajuste, Karlis; Gosteva, Marina; Sobolev, Arkadij; Tetrahedron; vol. 69; 26; (2013); p. 5550 – 5557;,
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20532-28-9, 5-Aminobenzothiophene is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,20532-28-9

EXAMPLE 61 Benzo[b]thiophen-5-yl-(6-methyl-pyrido[3,4-d]pyrimidin-4-yl)-aminehydrochloride This material was prepared from 6-methyl-pyrido[3,4-d]pyrimid -4-one (1.0 eq.) and 5-amino-benzo[b]thiophene (1.5 eq.) as described for Example 60. The polymer was filtered off and washed several times with 30% methanol/70% chloroform. Triethylamine (3.0 eq) was added to the filtrate and washings before they were concentrated in vacuo. The residue was flash chromatographed on silica in 10% methanol/methylenechloride to afford 135 mg of product as the free base (LC-MS: 293(MH+)). This material was dissolved in a minimum volume of chloroform and 1 mole equivalent of HCl in ether was added dropwise with stirring. The reaction mixture was diluted with ether (4volumes) and the precipitated title product was filtered and dried in vacuo (152 mg; M.P. 273-276 C.; LC-MS: 293 (MH+); anal. RP-HPLC:4.10 min.).

The synthetic route of 20532-28-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Pfizer Inc; US6395733; (2002); B1;,
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20699-85-8, Methyl 5-aminobenzo[b]thiophene-2-carboxylate is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,20699-85-8

A solution of 4-((ieri-butoxycarbonyl)amino)-i-methyl-iH-pyrrole-2-carboxylic acid (500 mg, 2.1 mmol) in A V-dimethylformamide (10 mL) was charged with i-(3- dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (725 mg, 3.8 mmol) and 4- (dimethylamino)pyridine (577 mg, 4.7 mmol). The reaction mixture was stirred at room temperature for 2 h. Methyl 5-aminobenzo[]thiophene-2-carboxylate 17 (392 mg, 1.9 mmol) was then added and the resulting mixture was stirred at room temperature for 16 h. This was then poured into ice-water (20 mL) and extracted with ethyl acetate (3 x 50 mL). The combined organic extracts were sequentially washed with 1 M citric acid (30 mL), a saturated aqueous solution of sodium hydrogen carbonate (35 mL), water (35 mL) and brine (35 mL). The organic layer was then dried over sodium sulfate, filtered and concentrated. The resulting residue was purified by column chromatography (silica), eluting with ethyl acetate/hexane (from 0% to 50%), to give the title compound 18 (610 mg, 75%) as a beige solid. (0901) MS (ES+): m/z = 430 (M+H)+; LCMS: tR = 7.90 min.

The synthetic route of 20699-85-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; FEMTOGENIX LIMITED; THURSTON, David Edwin; RAHMAN, Khondaker Mirazur; JACKSON, Paul Joseph Mark; (137 pag.)WO2016/198869; (2016); A1;,
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22913-24-2,22913-24-2, Methyl benzo[b]thiophene-2-carboxylate is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

fac-(NEt4)2[ReBr3(CO)3] (200 mg,0.260 mmol) was dissolved in methanol (10 ml). BSOC(24.98 mg, 0.130 mmol) was added as a solid and the resultingmixture was stirred at room temperature for 2 h. The productwas collected dried in vacuo (yield: 55 mg, 0.101 mmol, 78%). IR (KBr, cm-1): nuCO 2005, 1867.. UV-Vis: 211 nm,, epsilon = 2981 M-1 cm-1. 1H NMR(300 MHz, methanol-d4): delta 8.14 (s,1H), 8.02 (m, 2H), 7.51 (m, 2H), 3.92 (s, 3H). 13C NMR(150 MHz, methanol-d4): delta 143.4, 140.1, 138.0, 134.4, 131.8,128.2, 126.7, 126.2, 123.7. ICP-EOS: Recalcd: 34.33; Refound:34.39. Analysis calculated (%): C 28.79, H 1.49, S 5.91; found:C 28.19, H 1.42, S 5.82.

The synthetic route of 22913-24-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Nkoe, Pheello I.; Visser, Hendrik G.; Swart, Chantel; Brink, Alice; Schutte-Smith, Marietjie; Acta Crystallographica Section C: Structural Chemistry; vol. 74; (2018); p. 1116 – 1122;,
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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,5381-20-4

General procedure: Benzo[b]thiophene-3-carbaldehyde (40 mg, 0.25 mmol, 1.0 equiv),Pd(TFA) 2 (4.2 mg, 5 mol%), (4-FC 6 H 4 ) 3 P (9.5 mg, 12 mol%), DPEphos (8mg, 6 mol%), and Cs 2 CO 3 (122 mg, 0.375 mmol) were placed in atransparent Schlenk tube equipped with a stirring bar. The tube wasevacuated and filled with argon for three times. Degassed DMF (2.5mL) and tert-butyl bromide (51 mg, 0.375 mmol, 1.5 equiv) were add-ed via a gastight syringe. The reaction mixture was stirred under theirradiation of 36 W blue LEDs (distance app. 2.0-3.0 cm from thebulb) at r.t. for 24 h. The mixture was quenched with brine and ex-tracted with EtOAc (3 ¡Á 10 mL). The organic layers were combinedand concentrated under reduced pressure. The product was purifiedby flash column chromatography on silica gel using PE or a mixture of PEand EtOAc (10:1 v/v) as eluent; yield: 50.1 mg (92%); pale yellow liquid.

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

Reference£º
Article; Wang, Guang-Zu; Shang, Rui; Fu, Yao; Synthesis; vol. 50; 15; (2018); p. 2908 – 2914;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

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 6-bromobenzothiophene-3-carbaldehyde 915Benzothiophene-3-carbaldehyde (81 1 mg, 5 mmol, 1 equiv) 3a was dissolved in acetonitrile (15 ml.) and to this solution was slowly added bromine (1 ,29 ml_, 25 mmol, 5 equiv). The resulting reaction mixture was stirred at room temperature for 18 hour after which it was partitioned between an aqueous sodium bicarbonate solution (50 ml.) and EtOAc (50 ml_). To this biphasic solution was added dropwise, under vigorous stirring, a saturated aqueous sodium thiosulfate solution until discoloration of the organic medium. The organic layer was separated, and the aqueous layer was extracted with EtOAc (25 ml_). The organic fractions were combined, dried (MgS04), filtered and concentrated under vacuum. Purification through column chromatography (Rf0.14, EtOAc/PE: 1/13) yielded 6-bromobenzothiophene-3- carbaldehyde 9 (482 mg, 2 mmol, 40%) as a white powder. 9: 6-bromobenzothiophene-3-carbaldehyde 40% as white powder; Rf0.14 (EtOAc/PE: 1/13); m.p 1 1 1 C;1H-NMR (400 MHz, CDCI3): delta = 7.63 (dd, J = 8.7, 1.7 Hz, 1 H); 8.04 (d, J = 1.7 Hz, 1 H); 8.30 (s, 1 H); 8.56 (d, J = 8.7 Hz, 1 H); 10.12 (s, 1 H);13C-NMR (100.6 MHz, CDCIs): delta = 120.2, 125.0, 125.9, 129.6, 134.0, 136.1 , 141.8, 143.2 and 185.1 ; IR (cm”1): v = 1662 (C=0); Elemental Analysis Calcd (%) for C9H5BrOS: C 44.84 H 2.09; Found: C 45.17 H 1.71 .

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

Reference£º
Patent; UNIVERSITEIT GENT; DE VREESE, Rob; D’HOOGHE, Matthias; (52 pag.)WO2016/110541; (2016); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

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: A mixture of compound 9 or 10 (0.11 mmol), O-(7-aza-1H-benzotriazol-1-yl)-N,N,N’,N’-tetramethyluronium hexafluorophosphate (0.21mmol), and N,N-diisopropylethylamine (0.54 mmol) in dry DMF (1.5 mL) was stirred at 0 C for 30 min. The appropriate acid (0.16 mmol) was then added. After stirring at room temperature for 1-4 h, the reaction mixture was diluted with saturated aqueous NaHCO3, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous MgSO4, and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with EtOAc-hexane (1:1 to 1:3) to afford the corresponding compounds 11a-o and 12a-c.

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

Reference£º
Article; Koh, Eun Jeong; El-Gamal, Mohammed I.; Oh, Chang-Hyun; Lee, So Ha; Sim, Taebo; Kim, Garam; Choi, Hong Seok; Hong, Jun Hee; Lee, Sang-Gi; Yoo, Kyung Ho; European Journal of Medicinal Chemistry; vol. 70; (2013); p. 10 – 21;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem