Category: 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

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.

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

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

Synthesis of 2-(phenylethynyl)benzo[b]thiophene-3-carbaldehyde (29c): 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. I2 (381 mg, 1.5 mmol) dissolved in dry THF (2 mL) was then dropwise added and the resulting mixture was stirred for 0.5 h. To the solution of freshly generated in situ 2-iodobenzo[b]thiophene-3-carbaldehyde, NEt3 (7 mL), Cul (8 mg, 4 mol %), Pd(dba)2 (17 mg, 3 mol %) and P(o-furyl)3 (14 mg, 6 mol %) in THF (2 mL) and phenylacetylene (254 mg, 1.5 mol, 1.5 equiv) were successively slowly added. The reaction mixture was stirred at rt for 2 h. The reaction mixture was quenched with a sat. aq. Na2S2O3 solution (10 mL) and 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, 1:2) furnished compound 29c (165 mg, 63%) as a yellowish solid.m.p.: 104.9-106.5 C.1H-NMR (400 MHz, CDCl3) delta: 10.47 (s, 1 H), 8.69 (m, 1 H), 7.77 (m, 1 H), 7.60 (m, 2 H), 7.38-7.51 (m, 5 H).13C-NMR (100 MHz, CDCl3) delta: 185.6, 138.9, 138.5, 135.9, 135.2, 131.8, 129.8, 128.6, 126.8, 126.5, 124.9, 121.6, 121.3, 102.9, 80.0.MS (70 eV, El) m/z (%): 262 (100) [M+], 234 (38), 232 (13), 202 (11), 189 (13).IR (ATR) v (cm-1): 2969, 2832, 2359, 2340, 2203, 1739, 1661, 1587, 1569, 1507, 1481, 1458, 1442, 1427, 1361, 1316, 1293, 1250, 1229, 1216, 1177, 1162, 1141, 1119, 1070, 1059, 1043, 1015, 997, 953, 918, 868, 748, 737, 697, 687, 668, 630, 621, 616, 610.HRMS (El) for C17H10OS (262.0452): 262.0459.

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

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

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;,
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.

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;,
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.

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;,
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.

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;,
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

To a mixture of benzo[b]thiophene-3-carbaldehyde (10 g, 0.06 mol) and hydroxylamine hydrochloride (6.4 g, 0.09 mol) in anhydrous methyl alcohol (100 mL) was added potassium carbonate (12.4 g, 0.09 mol) at room temperature. The mixture was stirred at room temperature overnight. On completion, a filtration was performed and the residue was purified by silica gel chromatography eluting with petroleum ethenethyl acetate = 10: 1 to give compound B- 103 (7.0 g, 66% yield) as a white solid. LCMS: (ES+) m/z (M+H)+ = 178.1 , tR=0.725.

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

Reference£º
Patent; FORUM PHARMACEUTICALS, INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; MCRINER, Andrew, J.; WO2015/66371; (2015); 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

To a solution of 5′-chloro-2′-hydroxyacetophenone (50 mg, 0.29 mmol) in ethanol (1.5 mL)50% aqueous potassium hydroxide solution (1.5 mL) and thianaphthene-3-carbaldehyde (57 mg, 0.35 mmol) were added and the mixture was stirred at room temperature.Upon completion of the reaction, the reaction mixture was neutralized with 2N hydrochloric acid.The reaction mixture was extracted with ethyl acetate, and the obtained organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure.The residue was purified by silica gel column chromatography with hexane-methylene chloride (5: 1), methylene chloride and acetic acid effluent solvent,The fractions containing the desired product were collected and the solvent was distilled off under reduced pressure and then recrystallized from methanol. As a result,Compound [4] (14 mg, 0.043 mmol) was obtained as a yellow solid in 15% yield. The results of 1 H NMR and HRMS of the compound [4] are shown below.

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

Reference£º
Patent; KANAZAWA UNIVERSITY; MIZOKAMI, ATSUSHI; GOTO, KYOKO; SAITO, YOHEI; IZUMI, KOUJI; (29 pag.)JP2017/178941; (2017); A;,
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.

General procedure: The requisite aldehyde (0.560 mmol) was dissolved in EtOH (3 mL) before sequential addition of piperidine (0.056 mmol) and rhodanine (0.560 mmol). The flask was sealed, heated to 70 C for 16 h and cooled to room temperature. Water (10 mL) was added and the resulting precipitate filtered, washing with water, ice-cooled EtOH and Et2O. The remaining solid was collected and dried under vacuum.

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

Reference£º
Article; Bataille, Carole J.R.; Brennan, Meabh B.; Byrne, Simon; Davies, Stephen G.; Durbin, Matthew; Fedorov, Oleg; Huber, Kilian V.M.; Jones, Alan M.; Knapp, Stefan; Liu, Gu; Nadali, Anna; Quevedo, Camilo E.; Russell, Angela J.; Walker, Roderick G.; Westwood, Robert; Wynne, Graham M.; Bioorganic and Medicinal Chemistry; vol. 25; 9; (2017); p. 2657 – 2665;,
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.

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.1 H NMR (400 MHz, CDCl 3 ): delta = 10.75 (s, 1 H), 8.68 (d, J = 8.1 Hz, 1 H),7.76 (d, J = 8.0 Hz, 1 H), 7.47-7.43 (m, 1 H), 7.38-7.34 (m, 1 H), 1.66 (s,9 H).13 C NMR (101 MHz, CDCl 3 ): delta = 185.9, 172.5, 138.7, 135.6, 129.4,125.9, 125.0, 124.8, 121.3, 36.6, 33.3.HRMS (ESI): m/z calcd for C 13 H 15 OS + [M + H] + : 219.0838; found:219.0839.

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

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