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.

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

EXAMPLE 62 2-(3-Benzo[b]thienyl)-2-trimethylsiloxyethanenitrile Benzo[b]thiophene-3-carbaldehyde [1.8 g., 11 mmoles, J. Chem. Soc. C., pp. 339-340 (1969)] and about 100 mg. of zinc iodide were combined in 35 ml. of ether. Trimethylsilylcarbonitrile (1.98 g., 20 mmoles) was added dropwise. After approximately 1 hour, the reaction mixture was washed in sequence with saturated sodium bicarbonate, water and brine, dried over anhydrous sodium sulfate, filtered and evaporated to yield 2-(3-benzo[b]thienyl)-2-trimethylsiloxyethanenitrile [2.5 g., oil, Rf 0.7 (1:2 ethyl acetate:hexane)].

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

Reference£º
Patent; Pfizer Inc.; US4332952; (1982); A;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

 

Simple exploration of 5381-20-4

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

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.

General procedure: To a stirred solution of 5 (1 equiv.) in THF (~20 mL) was added dropwise a 2.0 M solution of lithium diisopropylamide (LDA) in THF/heptane/ethylbenzene (2.2 equiv.) at -78 C. The reaction mixture was stirred for 30 min at 0 C followed by dropwise addition of aldehyde (1.2equiv.). The solution was stirred for 16 h at room temperature, quenched by a saturated aqueous solution of NH4Cl and extracted with ethyl acetate. The organic phase was dried with MgSO4, evaporated, and the residue was purified by silica gel column chromatography

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

Reference£º
Article; Ishita, Keisuke; Stefanopoulos, Stavros; Khalil, Ahmed; Cheng, Xiaolin; Tjarks, Werner; Rappleye, Chad A.; Bioorganic and Medicinal Chemistry; vol. 26; 9; (2018); p. 2251 – 2261;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

 

Simple exploration of 5381-20-4

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

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.

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.

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

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

 

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: 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.

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

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

 

Brief introduction of 5381-20-4

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

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

4-Phenyl-piperidine-1-sulfonic acid amide (1.5 g, 6.24 mmol) was dissolved in ethanol (20 mL). Benzo[b]thiophene-3-carbaldehyde (1.0 g, 6.24 mmol) was then added and the reaction mixture was warmed to 45 C. overnight. The reaction mixture was cooled to room temperature and then treated with sodium borohydride (0.2 g, 5.29 mmol). The reaction was then quenched by addition of 1 N HCl. The reaction mixture was stirred overnight. The product precipitated from solution and was removed by vacuum filtration to yield the title compound as a white solid. 1H NMR (DMSO-d6): delta 7.99 (2H, q, J=12.0, 7.7 Hz), 7.86 (1H, dd, J=5.0 Hz), 7.66 (1H, s), 7.42 (2H, dt, J=14.0, 6.7 Hz), 7.35-7.24 (3H, m), 7.24-7.09 (2H, m), 4.37 (2H, d, J=5.8 Hz), 3.56 (2H, d, J=11.5 Hz), 2.75-2.59 (3H, m), 1.68 (2H, d, J=13.5 Hz), 1.31 (2H, dd, J=25.0, 13.5 Hz).

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

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

 

Some tips on 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 solution of an aromatic aldehyde 1 (0.500 mmol, 1.0 equiv) and TMSN3 (115 mg, 1.00 mmol,2.0 equiv) in a premixed HFIP/ACN mixture (2.0 mL, 1:1) in a nitrogen-flushed two dram vial wasadded triflic acid (TfOH; 17.7 L, 0.200 mmol, 0.40 equiv) (exotherm and brisk effervescence due tonitrogen gas evolution was immediately observed). The vial was capped and the reaction mixture wasallowed to stir at rt for 20-75 min. The reaction mixture was concentrated under nitrogen. The residueobtained was suspended in CH2Cl2/hexanes mixture and loaded on a silica gel in a 5 g samplecartridge. Purification using a normal phase silica flash column on a CombiFlash purification systemafforded a corresponding aromatic nitrile 2 upon concentration of appropriate fractions.

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

Reference£º
Article; Motiwala, Hashim F.; Yin, Qin; Aube, Jeffrey; Molecules; vol. 21; 1; (2016);,
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.

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., 5381-20-4

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

 

Some tips on 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: 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

 

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

General procedure: 3-Substituted propiolic acid (0.5 mmol) was dissolved in methanol (2 mL) followed by addition of appropriate 2-bromophenethylamine (0.5 mmol), aldehyde (0.5 mmol) and isocyanide (0.5 mmol). The reaction mixture was stirred at rt for 24 h in a sealed screw cap vial. The resulting mixture was concentrated and subjected to the column chromatography on silicagel with hepthane-EtOAc (15-40%) as eluent to give the desired propargylamides 7a-g,i.

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

Reference£º
Article; Peshkov, Anatoly A.; Peshkov, Vsevolod A.; Pereshivko, Olga P.; Van Der Eycken, Erik V.; Tetrahedron; vol. 71; 23; (2015); p. 3863 – 3871;,
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.

General procedure: To a solution of the appropriate aldehyde or ketone (1 eq.) in 50% aqueous ethanol (v/v), thiosemicarbazide (1 eq.) was added. The mixture was stirred at 60C for 2-12h, cooled at room temperature and diluted with water. The precipitate formed was collected and recrystallized from water and ethanol to give the desired product in 65-95% yield., 5381-20-4

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

Reference£º
Article; Linciano, Pasquale; Moraes, Carolina B.; Alcantara, Laura M.; Franco, Caio H.; Pascoalino, Bruno; Freitas-Junior, Lucio H.; Macedo, Sara; Santarem, Nuno; Cordeiro-da-Silva, Anabela; Gul, Sheraz; Witt, Gesa; Kuzikov, Maria; Ellinger, Bernhard; Ferrari, Stefania; Luciani, Rosaria; Quotadamo, Antonio; Costantino, Luca; Costi, Maria Paola; European Journal of Medicinal Chemistry; vol. 146; (2018); p. 423 – 434;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem