Analyzing the synthesis route of 5381-20-4

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

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: To a solution of aldehyde 1 (1 equiv.) in tetrahydrofuran (THF) was slowly added 1.0 M allyl magnesium bromide (2 equiv.) at 0 oC. Some of the aldehydes 1f-1m, 1w, and 1x were treated with the solution of zinc and allyl bromide instead of allyl magnesium bromide because allyl magnesium bromide did not work properly. The reaction mixture was warmed to room temperature and stirred for 2-12 h. Saturated NH4Cl aqueous solution was added to the mixture and it was poured into ethyl acetate and extracted with ethyl acetate 2 times. The combined organic layers were washed with brine, dried with Na2SO4, filtered, and concentrated. The residue was purified by silica gel column chromatography (Hexane/Ethyl acetate) to give compounds 2 (26-99% of yield).

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

Reference£º
Article; Lee, Sun-Mi; Lee, Won-Gil; Kim, Young-Chul; Ko, Hyojin; Bioorganic and Medicinal Chemistry Letters; vol. 21; 19; (2011); p. 5726 – 5729;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

 

Brief introduction of 5381-20-4

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

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 solution of arylcarbaldehyde (10.4 mmol) and (ethoxycarbonylmethylene)triphenylphosphorane (14.6 mmol) in THF (20 mL) was heated at 80 C for 12 h. After cooling to an ambient temperature, the reaction mixture was quenched with water, and then was extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, and evaporated in vacuo. The residue was purified by column chromatography (silica gel, 30 g) using EtOAc-hexane (3:97, v/v) as an eluent to give the (E)-acrylate 9.

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

Reference£º
Article; Nishiyama, Takashi; Hatae, Noriyuki; Hayashi, Kaori; Obata, Manami; Taninaka, Kimiko; Yamane, Masahiro; Oda, Shota; Abe, Takumi; Ishikura, Minoru; Hibino, Satoshi; Choshi, Tominari; Heterocycles; vol. 95; 1; (2017); p. 251 – 267;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

 

New learning discoveries about 5381-20-4

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

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, Thianaphthene-3-carboxaldehyde (5 g, 30.8 mmol) was dissolved in THF (50 mL). Sulfamide (12.22 g, 123.30 mmoles) and sulfamic acid (0.29 g, 3.08 mmoles) were added and the reaction mixture heated to 45 C. for 18 h. The reaction mixture was then cooled to room temperature and filtered through a sintered glass funnel. The resulting solution was treated with lithium borohydride (2.0 M in THF, 5 mL, 10 mmol) via addition funnel. After addition (5 minutes) the reaction mixture was stirred for 1 hour. 1 N HCl (20 mL, 20 mmol) was added and the reaction mixture concentrated to remove THF. The resulting suspension was treated with water (100 mL) and vigorously stirred. The resulting solid was filtered and dried to yield the title compound as a light pink solid. 1H NMR (DMSO-d6): delta 7.98 (1H, dd, J=6.5, 2.3 Hz), 7.92 (1H, dd, J=6.6, 2.4 Hz), 7.62 (1H, s), 7.36-7.45 (2H, m), 7.08 (1H, t, J=6.3 Hz), 6.72 (2H, s), 4.31 (2H, d, J=6.3 Hz).

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

Reference£º
Patent; Abdel-Magid, Ahmed F.; Mehrman, Steven J.; US2006/270856; (2006); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

 

Brief introduction of 5381-20-4

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

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 j (adapted from Lu Liu et al, Chem. Int. Ed. 2009, 48, 6093-6096) Intermediate j1: 3-(benzo[b]thiophen-3-ylmethylene)pentane-2,4-dione Benzo[b]thiophene-3-carbaldehyde (1 g, 6.16 mmol, 1 eq) was dissolved in toluene (0.5 M) at RT, and acetic acid (0.176 ml, 3.08 mmol, 0.5 eq), piperidine (0.061 ml, 0,61 mmol, 0.1 eq), molecular sieves (6 g) and 2,4-pentanedione (0.95 ml, 9.24 mmol, 1.5 eq) were added. The reaction mixture was heated in a microwave oven at 111 C until the disappearance of starting material (4 h). The mixture was allowed to cool to RT and then concentrated. The resulting residue was purified by flash column chromatography on silica gel using ethyl acetate/hexane (1:6) as eluent to afford the Knoevenagel product as a yellow solid (1.8 g, 60%). 1H-NMR (300 MHz, CDCl3) delta = 7.89 (t, J = 7.5 Hz, 2H), 7.76 (s, 1 H), 7.72 (s, 1 H), 7.48 (p, J = 7.4 Hz, 2H), 2.49 (s, 3H), 2.30 (s, 3H).

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

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

 

Downstream synthetic route of 5381-20-4

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

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 benzo[b]thiophene-3-carbaldehyde1 (1.62 g, 10 mmol) in ethanol (5 mL), 2-ethanonederivatives (2a, 2b) (10 mmol) dissolved in ethanol(2-3 mL) was added portion wise (Scheme 1). The reactionmixture was stirred at room temperature for 20 min,during which it turned to a homogeneous solution. ThenKOH solution (40 %, 2 mL) was added drop wise and theresultant mixture was stirred at room temperature for3-4 h. The precipitated product of chalcone was thencollected by filtration. The crude product was purified byrecrystallization from chloroform-methanol (1:1 v/v,10 mL) to afford (80-85 % yield) the product as yellow tolight brown needles (3a, 3b). Single crystals suitable forX-ray diffraction of both of the chalcones were obtained byrecrystallization from a saturated solution in DMSO.

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

Reference£º
Article; Patel, Paresh N.; Chadha, Anju; Journal of Chemical Crystallography; vol. 46; 5; (2016); p. 245 – 251;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

 

New learning discoveries about 5381-20-4

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

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

 

Downstream synthetic route of 5381-20-4

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

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

Thianaphthene-3-carboxaldehyde (1.62 g, 10.0 mmol) was dissolved in anhydrous ethanol (50 mL). Sulfamide (4.0 g, 42 mmol) was added and the mixture was heated to reflux for 16 hours. The mixture was cooled to room temperature. Sodium borohydride (0.416 g, 11.0 mmol) was added and the mixture was stirred at room temperature for three hours. The reaction was diluted with water (50 mL) and extracted with chloroform (3¡Á75 mL). The extracts were concentrated and chromatographed (5% methanol in DCM) to yield the title compound as a white solid.1H NMR (DMSO-d6): delta 7.98 (1H, dd, J=6.5, 2.3 Hz), 7.92 (1H, dd, J=6.6, 2.4 Hz), 7.62 (1H, s), 7.36-7.45 (2H, m), 7.08 (1H, t, J=6.3 Hz), 6.72 (2H, s), 4.31 (2H, d, J=6.3 Hz).

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

Reference£º
Patent; Smith-Swintosky, Virginia L.; US2007/191461; (2007); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

 

Downstream synthetic route of 5381-20-4

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

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: 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

 

Simple exploration of 5381-20-4

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

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: 3-(2-Methyl-5,6,7,8-hydrobenzo[4,5]-thieno[2,3-d]pyrimidin-4-yl)-2-thioxothiazolidin-4-one 7 (0.2 g,(0.60 mmol, 1 equiv) and aromatic aldehyde (0.77 mmol, 1.3 equiv). were thoroughly mixed then placedinto a specially designed microwave test tube containing 5 mL EtOH and three drops of piperidine. Thecharged tube was heated for 25 min at 100 C and 250 psi pressure. After cooling, the solid mass wasplaced in 50 mL cold EtOH and crushed. The slurry was filtered to give a solid that was washed severaltimes with EtOH/hexane mix (20%, v/v), then dried under vacuum to give the corresponding 5-aryl/hetaryl-2-thiocothiazolidine-4-one (8a-o) whose structures were identified by IR, LC/MS, GC/MS andNMR analysis. The physical and spectral properties of these compounds are shown later in the experimentalsection

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

Reference£º
Article; Mendoza, Kimberly; Kamila, Sukanta; Biehl, Edward R.; Heterocycles; vol. 88; 1; (2014); p. 741 – 753;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

 

Downstream synthetic route of 5381-20-4

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

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: 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