Tag: 5381-20-4

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: 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.

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

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);,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

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: Titanium tetrachloride (1.90 g, 10 mmol) was slowly added to100 mL of anhydrous THF at 0 C, followed by addition of 5 mmol of the aldehyde (1) and stirred for 10 min, then ethyl 2-(3-bromopyridin-2-yl)acetate (2) (1.47 g, 6 mmol) was added. Subsequently, a solution of pyridine (3.16 g, 40 mmol) in 25 mL of anhydrous THF was added dropwise during a period of 30-60 min at 0 C. The reaction mixture was then stirred for 1 h at room temperature and refluxed for 24 h. After that the mixture was poured on to crashed ice and extracted with ethyl acetate (4 30 mL). The combined extracts were successively washed with brine, saturated sodium hydrogen carbonate and brine, and then dried over anhydrous MgSO4. The organic phase was filtrated and the solvent was removed in vacuo, the residue was purified by column chromatography (silica gel) using PE/EA (5:1) / DCM/MeOH (50:1) to provide 3.

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

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Article; Li, Bo; Yue, Zhi-Zhou; Feng, Jian-Ming; He, Qian; Miao, Ze-Hong; Yang, Chun-Hao; European Journal of Medicinal Chemistry; vol. 66; (2013); p. 531 – 539;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

5381-20-4, Thianaphthene-3-carboxaldehyde is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of thianaphthene-3-carboxaldehyde (0.106 g, 0.65 mmol), methyl 3-cyclopropyl-3-oxopropanoate (0.071 g, 0.72 mmol) and 4-amino-3-penten-2-one (0.088 g, 0.61 mmol) and acetic acid (0.035 mL) in isopropylalcohol (1.5 mL) was heated to 100C and left to stir for 19 hours. The mixture was allowed to cool to RT and was then treated with saturated aqueous sodium bicarbonate solution (10 mL). The solid was filtered off, washed with water, dried and purified by column chromatography (4:1 hexane: ethyl acetate) affording a fine yellow solid (0.075 g, 44 %). 1H-NMR (400 MHz, DMSO-d6) delta = 0.76 (s, 2H), 0.96 (d, 2H), 2.12 (s, 3H), 2.33 (s, 3H), 2.69 (s, 1H), 3.58 (s, 3H), 5.43 (s, 1H), 7.15 (s, 1H), 7.31 (s, 1H), 7.38 (s, 1H), 7.90 (s, 2H), 8.05 (d, 1H). HPLC-MS: Rt 4.302 min, m/z 234.1 (MH+-133). (0600) A second reaction product was isolated by column chromatography: Example J1-a: Dimethyl 4-(benzo[b]thiophen-3-yl)-2,6-dicyclopropyl-1,4-dihydropyridine-3,5-dicarboxylate (0601) 1H-NMR (400 MHz, DMSO-d6) delta = 0.56 (s, 2H), 0.82 (s, 2H), 0.90 (d, 2H), 1.04 (s, 2H), 2.56 (m, 2H), 3.55 (s, 5H), 5.37 (s, 1 H), 7.05 (s, 1 H), 7.11 (s 1 H), 7.32 (t, 1 H), 7.39 (t, 1H), 7.90 (d, 1 H), 7.98 (s, 1 H). HPLC-MS: Rt 4.935; m/z 276.1 (MH+)., 5381-20-4

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

Reference£º
Patent; Oncostellae, S.L.; KURZ, Guido; CAMACHO GOMEZ, Juan; (123 pag.)EP3480201; (2019); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

5381-20-4,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 11 Synthesis of N-benzo[b]thio-ohen-3-yl-methylidene-N’-(8-morpholin-4-yl-2-pyridin-4-yl-imidazo[1,2-b]pyridazin-6-yl)-hydrazine (Compound 11) (8-Morpholin-4-yl-2-pyridin-4-yl-imidazo[1,2-b]pyridazin-6-yl)-hydrazine (16.2mg, 0.0520mmol) was dissolved in ethanol (2mL). Thionaphthene-3-carboxyaldehyde (9.3mg, 0.057mmol) was added thereto and stirred at room temperature for 2 hours. Then, the reaction liquid was filtered, and the obtained solid material was washed with diethyl ether to obtain a title compound (21.6mg, 91%). The characteristic value of the compound is shown below. 1H-NMR (300 MHz, DMSO): delta 3.87-3.89 (m, 4H), 3.98-4.01 (m, 4H), 6.49 (s, 1H), 7.43-7.57 (m, 2H), 7.88 (d, 2H, J=6.2 Hz), 8.04 (d, 1H, J=7.6 Hz), 8.06 (s, 1H), 8.34 (s, 1H), 8.57 (d, 2H, J=6.2 Hz), 8.59 (s, 1H), 8.71 (d, 1H, J=8.2 Hz), 10.99 (s, 1H); MS (ESI) m/z 456 (M+H)+.

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

Reference£º
Patent; AJINOMOTO CO., INC.; EP2518072; (2012); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

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: In an oven-dried Schlenk tube equipped with a magnetic stir bar, the photocatalyst [Ir(dF-CH3-ppy)2(dtbpy)]PF6 (PC-1) (5.1 mg, 0.005 mmol, 1.0 mol%) was dissolved in MeCN (0.4 mL) andwater (0.1 mL) under an atmosphere of dry argon. In the absence of light, the respectivebenzothiophene (0.50 mmol, 1.0 equiv) and alkene (1.50 mmol, 3.0 equiv) were added in anargon stream. The reaction mixture was degassed by three freeze-pump-thaw cycles and thetube was finally backfilled with argon. The reaction was stirred under irradiation with visiblelight from two 30 W Kessil LED (lambdamax = 455 nm, see chapter 1.2 for emission spectrum). Afterthe indicated time, the solvent was removed in vacuo and the residue was purified by flashcolumn chromatography on silica gel to afford products 3a-3o as (mostly) inseparablemixtures of diastereomers.

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

Reference£º
Article; Strieth-Kalthoff; Henkel, Christian; Teders, Michael; Kahnt, Axel; Knolle, Wolfgang; Gomez-Suarez, Adrian; Dirian, Konstantin; Alex, Wiebke; Bergander; Daniliuc, Constantin G.; Abel; Guldi, Dirk M.; Glorius; Chem; vol. 5; 8; (2019); p. 2183 – 2194;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

5381-20-4,5381-20-4, Thianaphthene-3-carboxaldehyde is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a 20-mL sealed tube purged and maintained with an inert atmosphere of nitrogen,was placed a solution of 2-ethyl-5-[(3-methylcyclohexyl)oxyjaniline (1.0 g,4.29 mmol,as prepared in the previous step) in EtOH (10 mL) then 2-oxopropanoic acid (1.13 g,12.83 mmol) and 1-benzothiophene-3-carbaldehyde (626 mg,3.86 mmol) were added. The reaction was stirred overnight at 120C then concentrated under reduced pressure. The crude product was purified by Flash-PrepHPLC (IntelFlash-1: Column,C18; mobile phase,ACN,water (0.5% TFA) and ACN (80.0%ACN up to 95.0% in 15 mm); Detector,UV 254 nm) then the isomers were separated by PrepSFC (Prep 5FC350-2: Column,CHIRALPAK AD-H SFC,5*25cm,Sum; mobile phase,C02(50%),ethanol(2mM NH3-MeOH); Detector,UV 254 nm) affording 56.7 mg (3%) of 2-(1-benzothiophen-3-yl)-8-ethyl-5-[[(1 R,3 S)-3-methylcyclohexylj oxyl quinoline-4-carboxylic acid (Compound 182) as alight yellow solid,53.9 mg(4%) of 2-(1-benzothiophen-3-yl)-8-ethyl-5-[[(1 R,3R)-3-methylcyclohexyll oxyl quinoline-4-carboxylic acid (Compound 184) as a light yellow solid and a mixture of Compound 181 and Compound 183. This mixture was separated by Chiral-Prep-HPLC (HPLC-09: Column: CHIRALPAK-AD-H-5L002,20*250 mm; Mobile Phase A:Hex–HPLC,Mobile Phase B: IPA–HPLC; Flow rate: 15 mL/min; Gradient: 40 B to 40 B in 16 mm; 254 nm) affording 55.7 mg (3%) of 2-(1-benzothiophen-3-yl)-8-ethyl-5-[[(1 S,3R)-3-methylcyclohexyll oxyl quinoline-4-carboxylic acid (Compound 181) as a brown solid and 56.8 mg (3%) of 2-(1-benzothiophen-3-yl)-8-ethyl-5-[[(1 S,35)-3-methylcyclohexyljoxyjquinoline-4-carboxylic acid (Compound 183) as a brown solid. j0401j 2-(1-Benzothiophen-3-yl)-8-ethyl-5-j j(1S,3R)-3-methylcyclohexyljoxyjquinoline-4-carboxylic acid (Compound 181): Mass Spectrum(LCMS,ESI pos): Calcd. for C27H28NO3S: 446.2 (M+H); Found: 446.2. 1H NMR (300 MHz,DMSO-d6): oe 13.14 (brs,1H ),9.26 (d,J= 7.5 Hz,1H ),8.81 (s,1H ),8.12 (d,J= 7.8 Hz,1H ),8.04 (s,1H ),7.46-7.61 (m,3H),7.02 (d,J= 8.1H z,1H ),4.86-4.85 (m,1H ),3.25 (q,J= 7.5Hz,2H),1.97-1.72 (m,4H),1.70-1.61 (m,1H ),1.60-1.45 (m,2H),1.37 (t,J= 7.5 Hz,3H),1.10-0.93 (m,1H ),0.87 (d,J= 6.3 Hz,1H ). HPLC purity (254 nm): 99.5%.j0402j 2-(Benzo jbjthiophen-3-yl)-8-ethyl-5-(((1R,3S)-3-methylcyclohexyl)oxy)quinoline-4-carboxylic acid (Compound 182): Mass Spectrum(LCMS,ESI pos): Calcd. for C27H28NO3S: 446.2 (M+H); Found: 446.2. 1H NMR (300 MHz,DMSO-d6): oe 13.14 (brs,1H ),9.26 (d,J= 7.5 Hz,1H ),8.81 (s,1H ),8.12 (d,J= 7.8 Hz,1H ),8.04 (s,1H ),7.46-7.61 (m,3H),7.02 (d,J= 8.1H z,1H ),4.86-4.85 (m,1H ),3.25 (q,J= 7.5Hz,2H),1.97-1.72 (m,4H),1.70-1.61 (m,1H ),1.60-1.45 (m,2H),1.37 (t,J 7.5 Hz,3H),1.10-0.93 (m,1H ),0.87 (d,J= 6.3 Hz,1H ). HPLC purity (254 nm): 99.7%.j0403j 2-(Benzo jbjthiophen-3-yl)-8-ethyl-5-(((1S,3S)-3-methylcyclohexyl)oxy)quinoline-4-carboxylic acid (Compound 183): Mass Spectrum(LCMS,ESI pos): Calcd. for C27H28NO3S: 446.2 (M+H); Found: 446.2. 1H NMR (300 MHz,DMSO-d6): oe 13.14 (s,1H ),9.27 (d,J= 7.8 Hz,1H ),8.81 (s,1H ),8.12 (d,J 7.8 Hz,1H ),8.04 (s,1H ),7.46-7.61 (m,3H),7.11 (d,J= 8.1H z,1H ),4.50-4.57 (m,1H ),3.24 (q,J= 7.5Hz,2H),2.10-2.13 (m,2H),1.47-1.80 (m,3H),1.29-1.43 (m,5H),1.10-1.28 (m,1H ),0.94 (d,J= 6.6 Hz,3H),0.79-0.89 (m,1H ). HPLC purity (254 nm): 99.6%.j0404j 2-(Benzo jbjthiophen-3-yl)-8-ethyl-5-(((1R,3R)-3-methylcyclohexyl)oxy)quinoline-4-carboxylic acid (Compound 184): Mass Spectrum(LCMS,ESI pos): Calcd. for C27H28NO3S: 446.2 (M+H); Found: 446.2. 1H NMR (300 MHz,DMSO-d6): oe 13.14 (s,1H ),9.27 (d,J= 7.8 Hz,1H ),8.81 (s,1H ),8.12 (d,J 7.8 Hz,1H ),8.04 (s,1H ),7.46-7.61 (m,3H),7.11 (d,J= 8.1H z,1H ),4.50-4.57 (m,1H ),3.24 (q,J= 7.5Hz,2H),2.10-2.13 (m,2H),1.47-1.80 (m,3H),1.29-1.43 (m,5H),1.10-1.28 (m,1H ),0.94 (d,J= 6.6 Hz,3H),0.79-0.89 (m,1H ). HPLC purity (254 nm): 99.7%.

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

Reference£º
Patent; PROTEOSTASIS THERAPEUTICS, INC.; MUNOZ, Benito; BASTOS, Cecilia, M.; PARKS, Daniel; KOMBO, David; (301 pag.)WO2017/62581; (2017); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

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;,
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

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.

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Article; Pommidi, Anil; Shaik, Asha Begum; Chatterjee, Anindita; Somarapu, Vijaya Laxmi; Journal of the Iranian Chemical Society; (2020);,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

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.

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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