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: As a typical experiment, the reaction of the aryl bromide (1 mmol), benzothiophene (1.5 mmol) and KOAc (0.196 g, 2 mmol) at 150C during 16 h in DMF or DMAc (4 mL) in the presence of Pd(OAc)2 (0.224 mg,0.001 mmol) or (1.12 mg, 0.005 mmol) prepared as a solution in DMAc (1 mg of Pd(OAc)2 in 1 mL of DMAc) under argon affords the coupling product after evaporation of the solvent and purificationon silica gel.

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

Reference:
Article; Zhao, Liqin; Bruneau, Christian; Doucet, Henri; Tetrahedron; vol. 69; 34; (2013); p. 7082 – 7089;,
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.

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 × 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.

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

Reference:
Article; Wang, Guang-Zu; Shang, Rui; Fu, Yao; Synthesis; vol. 50; 15; (2018); p. 2908 – 2914;,
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, Step 1 : Preparation of intermediate methyl 2-(1 -benzothiophen-3-yl)-2- hydroxyacetate (4a)Trimethylsilylcyanide (924 muIota_, 7.39 mmol) was added at 0C to a solution of thianaphtene-3-carboxaldehyde (1 g, 6.16 mmol) and zinc iodide(ll) (198 mg, 0.62 mmol) in anhydrous dichloromethane (40 mL) under a nitrogen atmosphere. After 2 hours, the reaction mixture was quenched with a saturated aqueous solution of sodium carbonate and extracted with dichloromethane (2 x 20 mL). The organic layer was washed with brine (10 mL), dried over sodium sulfate, filtered and evaporated to dryness. The residue was dissolved in anhydrous methanol and the solution was cooled at 0C. Hydrogen chloride was bubbled for 5 minutes. The mixture was then warmed at room temperature for 20h and concentrated in vacuo. The residue was partitioned between ethyl acetate (10 mL) and a saturated aqueous solution of sodium bicarbonate (10mL). The aqueous layer was extracted with ethyl acetate (2×1 OmL). The organic layer was washed with brine (10 mL), dried over sodium sulfate, filtered and evaporated to dryness. The residue was purified by flash chromatography on silica gel (dichloromethane/ethanol 95/5) to afford the desired alcohol (4a) as a white solid (550 mg, 2.47 mmol, 40%). 1H NMR (400 MHz, CDCI3) delta 3.78 (s, 3H), 5.56 (s, 1 H), 7.35-7.45 (m, 2H), 7.49 (s, 1 H), 7.86-7.92 (m, 2H).MS m/z ([M-OH]+) 205.

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

Reference:
Patent; LABORATOIRE BIODIM; CHASSET, Sophie; CHEVREUIL, Francis; LEDOUSSAL, Benoit; LE STRAT, Frederic; BENAROUS, Richard; WO2012/137181; (2012); A1;,
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

General procedure: A mixture of malononitrile (1.1 mmol) and substituted aldehydes(1.0 mmol) in ethanol in the presence of triethylamine wasstirred at room temperature. After the complete disappearance ofboth starting materials (monitored by TLC), 2-thioxo-1, 3-thiazolidin-4-one (1.0 mmol) was added and the stirring wascontinued for 2 -2hrs. The completion of the reaction wasmonitored by TLC. The solid formed in the reaction mixture wasfiltered, dried and recrystallized in ethanol to obtain the pureproduct in good yields., 5381-20-4

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

Reference:
Article; Noorulla; Suresh, Ayyadurai Jerad; Devaraji, Vinod; Mathew, Bijo; Umesh, Devi; Journal of Molecular Structure; vol. 1147; (2017); p. 682 – 696;,
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.

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

There was suspended, in ethanol (3.0 mL), 5-chloro-7-morpholin-4-yl-2-pyridin-4-yl-pyrazolo[1,5-a]pyrimidine (80 mg, 0.26 mM), then acetic acid (7.4 muL, 0.13 mM) and thianaphthene-2-carboxy-aldehyde (46 mg, 0.29 mM) were added to the suspension and the mixture was stirred at room temperature for one hour. This reaction liquid was filtered and the resulting solid was washed with ethanol and then with diethyl ether to thus give the title compound (3.4 mg, yield: 2.9%). 1H-NMR (300 MHz, DMSO-d6); delta 3.80 (bs, 4H), 3.94 (bs, 4H), 6.41 (s, 1H), 6.78 (s, 1H), 7.49 (t, 1H, J=6.9 Hz), 7.59 (t, 1H, J=6.9 Hz), 7.93 (d, 2H, J=6.3 Hz), 8.08 (d, 1H, J=7.8 Hz), 8.14 (s, 1H), 8.41 (s, 1H), 8.67 (d, 2H, J=6 Hz), 8.74 (d, 2H, J=7.8 Hz); MS (ESI) m/z 456 (M+H)+.

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

Reference:
Patent; AJINOMOTO CO., INC.; US2011/294781; (2011); 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.

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

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

Reference:
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

 

Simple exploration 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 round-bottom flask equipped with a magnetic stirring bar were added 3-diazoindolin-2-imines 1 (0.1mmol), aryl aldehydes (2) (0.15mmol), BF3·OEt2 (0.1mmol), and ethyl acetate (1mL) under air atmosphere. The mixture was stirred at room temperature for 2h. The resulted mixture was evaporated under reduced pressure and the residue was purified by flash column chromatography on a silica gel with petroleum ether/ethyl acetate (6:1, v/v) to give pure products 3.

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

Reference:
Article; Huang, Kai; Lu, Ping; Wang, Yanguang; Tetrahedron; vol. 75; 27; (2019); p. 3779 – 3787;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

 

Analyzing the synthesis 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

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

 

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

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*75 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).

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

Reference£º
Patent; Smith-Swintosky, Virginia L.; Parker, Michael H.; Reitz, Allen B.; Maryanoff, Bruce E.; US2007/293476; (2007); 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, To dry ethanol (20 mL) was added benzo[b]thiophene-3-carbaldehyde (246 mg, 1.52 mmol) and sodium borohydride (115 mg, 3.03 mmol), and the reaction was stirred at room temperature for 90 mins. When the reaction was complete by TLC, excess sodium borohydride was quenched with sodium hydroxide solution (1%, 20 mL), and the reaction was extracted with ethyl acetate (3 ¡Á 20 mL) before being dried (MgSO4), filtered and concentrated in vacuo to yield the title product in quantitative yield (249 mg). Rf = 0.40 (5:2 petroleum ether: ethyl acetate); 1H NMR (300 MHz, CDCl3): deltaH = 7.90 – 7.83 (2H, m, Ar), 7.44 – 7.34 (3H, m, Ar), 4.92 (2H, s, CH2), 1.95 (1H, br s, OH); 13C NMR (75 MHz, CDCl3) deltaC = 140.87 (Ar), 137.75 (Ar), 136.04 (Ar), 124.69 (Ar), 124.32 (Ar), 123.95 (Ar), 122.99 (Ar), 122.05 (Ar), 59.88 (CH2); MS (EI): m/z 164 (M).

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

Reference£º
Article; Sherer, Christopher; Tolaymat, Ibrahim; Rowther, Farzana; Warr, Tracy; Snape, Timothy J.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 7; (2017); p. 1561 – 1565;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem