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

Potassium hydroxide (3.11 g) and water (0.12 ML) are added to acetonitrile (50 ML). TRIMETHYLSULFONIUM iodide (5.65 g) and thianapthene-3-carboxaldehyde (4.50 g) are then added. The reaction mixture is heated to 60 C for 4 h. The reaction mixture is allowed to cool to room temperature and is then diluted with Et20 (25 ML). The precipitate is filtered off, and the filtrate is concentrated in vacuo. The resulting crude epoxide (6.20 g) is dissolved in methanol (40 ML) and added to a 2.0 M solution of methyl amine in methanol (100 mL). The reaction mixture is stirred at room temperature for 3 d. The reaction mixture is concentrated in vacuo. The resulting brown oil is PURIFIED VIA COLUMN CHROMATOGRAPHY (CHCL3/METHANOL, 95/5,90/10 ; CHC13/METHANOINI-LOH, 90/10/1) to yield 1.753 g of the title compound as a yellow solid. Physical characteristics. M. p. 98-102C ; 1H NMR (400 MHz, DMSO-d6) 8 7.98-7. 90,7. 51,7. 60, 7.40-7. 33,5. 43,5. 04,2. 80, 2.34 ; MS (ESI+) m/z 208 (M+H) +.

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

Reference£º
Patent; PHARMACIA & UPJOHN COMPANY; WO2004/106345; (2004); A2;,
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 mixture of the compound 15 (190.2 mg, 1.0 mmol) and 2-thiophenecarboxaldehyde (123.4 mg, 1.1 mol) in anhydrous ethanol (3.0 mL) was stirred over night at room temperature or reflux temperature. The corresponding imine was reduced with solid sodium borohydride (75.7 mg, 2.0 mmol) which was added slowly, the mixture was further stirred over night at room temperature. An additional ethanol (2.0 mL) was added to the reaction vessel after which 10% hydrochloric acid aqueous solution was added to quench excess sodium borohydride. The acidic mixture was basified with 25% aqueous ammonia solution. The desired product was extracted with dichloromethane (3 20 mL) and the solution was dried over sodium sulphate anhydrous. The solvent was removed under reduced pressure and the residue was purified by flash chromatography on silica gel, eluting with a gradient of 40-60% ethyl acetate in petroleum ether to give the title compound 17a1 [164.9 mg, 57.6% (from 15)] as a white solid, mp 100-101 C.

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

Reference£º
Article; Zhong, Zhao-Jin; Zhang, Da-Jun; Peng, Zong-Gen; Li, Yu-Huan; Shan, Guang-Zhi; Zuo, Li-Min; Wu, Lin-Tao; Li, Si-Yang; Gao, Rong-Mei; Li, Zhuo-Rong; European Journal of Medicinal Chemistry; vol. 69; (2013); p. 32 – 43;,
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.

Mix an aliquot (1 niL) of a 0.25 M solution of (S)-[l-(6-fluoropyridin-3-yl)- pyrrolidin-3-yl] -amine (0.25 mmol) in toluene, an aliquot (1 mL) of a 1.0 M solution of benzo [delta]thiophene-3-carboxaldehyde (1.0 mmol) in toluene and add a single activated 4A molecular sieve. Stir the reactants at room temperature in air. After 16 h add PS- Trisamine (1.5 mmol) and another single activated 4A molecular sieve. Stir the reactants at room temperature in air. After 24 h filter the reaction solution to remove the PS- Trisamine, and add an aliquot (2 mL) of a 0.25 M solution of sodium borohydride (0.5 mmol) in ethanol. Stir the reactants at room temperature in air. After 48 h add methanol (2 mL) to the reactants and agitate vigorously. Remove the excess reactants by ion- exchange chromatography using a 5g SCX-2 cartridge (0.5 mmol/g SO3H) by wetting it with one column volume of methanol. Apply the mixture to the cartridge and allow it to percolate through the stationary phase (under gravity) into a vial. Wash the cartridge with one column volume of methanol such that these washings also pass into the vial. Replace with a second vial and elute with 3.5N ammonia in methanol (10 mL). Evaporate the solvents from the ammonia washings on a heating block under a stream of nitrogen to give the title compound. 1H NMR (400 MHz, DMSOd6) delta 7.90-7.98 (2H, m)5 7.57 (IH, s), 7.39-7.42 (IH, m), 7.35-7.39 (2H, m), 7.08-7.13 (IH5 m), 6.96 (IH5 dd, J = 8.93, 3.30 ‘ Hz), 4.01 (2H5 S)5 3.43-3.50 (2H5 m), 3.20-3.27 (IH5 m), 3.17 (IH5 d, J = 5.14 Hz)5 3.07- 3.13 (IH5 m), 2.10-2.18 (IH5 m), 1.87-1.95 (IH5 m), MS (ES): m/z = 328 [M+H].

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

Reference£º
Patent; ELI LILLY AND COMPANY; WO2006/44454; (2006); 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

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

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

3-Benzo[b]thiophen-3-yl-3-hydroxy-propionitrile. (0168) To a stirring solution of diisopropylamine (0.93 mL, 6.58 mmol) in tetrahydrofuran (8 mL) at -78 C. under nitrogen was added a solution of n-butyllithium (2.75 mL, 6.88 mmol, 2.5 M in hexane). After the addition was complete, the mixture was stirred at -78 C. for 10 minutes and removed cooling bath for 5 minutes. The mixture was cooled back to -78 C., acetonitrile (0.31 mL, 5.98 mmol) was added and the reaction mixture was then stirred at -78 C. for 30 minutes. Benzo[b]thiophene-3-carbaldehyde (1 g, 5.98 mmol) in tetrahydrofuran (4 mL) was added and the resulting solution was allowed to warm to ambient temperature. After 18 hours at ambient temperature, saturated aqueous ammonium chloride (5 mL) was added to the reaction mixture and it was concentrated at reduced pressure. The resulting crude product was diluted with ethyl acetate (20 mL), washed with water (10 mL) followed by saturated aqueous sodium chloride (10 mL). The organic layer was concentrated and purified by column chromatography (80 g silica gel cartridge) eluting with ethyl acetate/hexane (30%-50%) to give the product as a light yellow oil (1.2 g, 99%).

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

Reference£º
Patent; Fox Chase Chemical Diversity Center, Inc.; Advanced Neural Dynamics, Inc.; Smith, Garry Robert; Brenneman, Douglas E.; Reitz, Allen B.; Zhang, Yan; Du, Yanming; US8609849; (2013); B1;,
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

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.

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

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