Simple exploration of 5381-25-9

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5381-25-9,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.5381-25-9,1-Benzothiophene-3-carboxylic acid,as a common compound, the synthetic route is as follows.

Benzothiophene-3-carboxylate 2h (eq. 1, 0.624mmol) and SOCl2 (1.5 eq, 0.936mmol) in toluene was heated at reflux for 2h.The reaction was detected by TLC. After the reaction was completed, the reaction mixture was concentrated under reduced pressure to give benzo[b]thiophene-3-carbonyl chloride as a crude product.This was dissolved in 5 mL of dichloromethane, and aqueous ammonia (25% aqueous ammonia solution, 1 mL) was added dropwise thereto under ice-cooling, and stirred at room temperature.The reaction was detected by TLC. After the reaction was completed, it was washed with dilute hydrochloric acid, and then extracted with ethyl acetate (3¡Á30 mL), and then washed with saturated brine and dried over anhydrous sodium sulfate.Concentration and purification with a mobile phase of petroleum ether and ethyl acetate (V/V = 2 / 1) over silica gel column to afford white solid benzo[b]thiophene-3-carboxamide 4h as 99.5mg.4h (1 equivalent, 0.562 mmol) of benzo[b]thiophene-3-carboxamide was dissolved in 5 mL of anhydrous THF, and LiAlH4 (3 eq., 1.686 mmol) was added portionwise in an ice bath, and the mixture was refluxed for 4 hours. .After the reaction was completed, the reaction was quenched by sequentially adding 0.4 mL of H 2 O, 0.4 mL of 15% NaOH solution, and 1.2 mL of H 2 O.Ethyl acetate was added, the suspension was filtered, and the filtrate was dried over anhydrous sodium sulfate, and then the solvent was evaporated under vacuo to give benzo[b]thiophen-3-ylmethylamine as a crude product.

As the paragraph descriping shows that 5381-25-9 is playing an increasingly important role.

Reference£º
Patent; Wuhan University; Wu Shuwen; Zhou Haibing; Lan Ke; Yu Yongshi; (21 pag.)CN108129454; (2018); A;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

 

Some tips on 5381-25-9

As the paragraph descriping shows that 5381-25-9 is playing an increasingly important role.

5381-25-9, 1-Benzothiophene-3-carboxylic acid is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Production example 10370 mg of oxalyl chloride was added to a mixture of 400 mg of benzo[b]thiophene-3-carboxylic acid and 20 ml of methanol under ice cooling. This mixture was stirred for 2 hours at 80C. After being cooled to room temperature, the reaction mixture was concentrated under reduced pressure. Tert-butyl methyl ether was added to the residues, and the residue was washed with an aqueous saturated sodium hydrogen carbonate solution and saturated saline. The organic layer was dried over magnesium sulfate and then concentrated under reduced pressure, thereby obtaining 380 mg of methyl benzo[b]thiophene-3-carboxylate (hereinafter, described as a “compound 12 of the present invention”).1H-NMR (CDCl3) delta: 8.60 (m, 1H), 8.39 (s, 1H), 7.88 (m, 1H), 7.49 (m, 1H), 7.43 (m, 1H), 3.97 (s, 3H), 5381-25-9

As the paragraph descriping shows that 5381-25-9 is playing an increasingly important role.

Reference£º
Patent; Sumitomo Chemical Company Limited; MUKUMOTO, Fujio; TAMAKI, Hiroaki; KUSAKA, Shintaro; IWAKOSHI, Mitsuhiko; EP2923573; (2015); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

 

New learning discoveries about 5381-25-9

The synthetic route of 5381-25-9 has been constantly updated, and we look forward to future research findings.

5381-25-9, 1-Benzothiophene-3-carboxylic acid is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,5381-25-9

To a stirred solution OF 4- [ (Z)- (4-BROMOPHENYL) (ethoxyimino) methyl]-1- (4-methyl-4- piperidinyl) piperidine (50 mg, 0.12 MMOL), benzo [b] thiophene-3-carboxylic acid (22 mg, 0.13 MMOL), and Et3N (24.3 mg, 0.24 MMOL) in DMF (2 ML), HATU (61 mg, 0.16 MMOL) was added at room temperature. After 16 h the mixture was poured into ice water (10 mL), and was extracted with CH2CI2 (3X10 mL). The organic phase was dried over NA2SO4, and concentrated in vacuo. Purification by preparative TLC afforded title compound as a white solid. MS: 569 (M++1).

The synthetic route of 5381-25-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; SCHERING AKTIENGESELLSCHAFT; WO2004/113323; (2004); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

 

Downstream synthetic route of 5381-25-9

The synthetic route of 5381-25-9 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.5381-25-9,1-Benzothiophene-3-carboxylic acid,as a common compound, the synthetic route is as follows.

5381-25-9, General procedure: A mixture of the corresponding carboxylic acid (12.3mmol) and thionyl chloride (6 ml, 83 mmol) in 40 ml of dry dichloromethane (DCM) was stirred under reflux for 6 h. After cooling to room temperature, DCM and excess thionyl chloride were evaporated under reduced pressure. The residue was treated without further purification.

The synthetic route of 5381-25-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Sweidan, Kamal; Engelmann, Joern; Rayyan, Walid Abu; Sabbah, Dima; Zarga, Musa Abu; Al-Qirim, Tariq; Al-Hiari, Yusuf; Sheikha, Ghassan Abu; Shattat, Ghassan; Letters in drug design and discovery; vol. 12; 5; (2015); p. 417 – 429;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

 

Analyzing the synthesis route of 5381-25-9

Big data shows that 5381-25-9 is playing an increasingly important role.

5381-25-9, 1-Benzothiophene-3-carboxylic acid is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: The starting aryl carboxylic acid (1.0 equiv) was added as a 0.5 M solution in dry CH2Cl2 to a dry round-bottom flask charged with a stir bar under nitrogen atmosphere. The solution was then cooled to 0C. Catalytic DMF (few drops to 1mL) was then added. Oxalyl chloride (1.2 equiv) was added over 1min with stirring at 0C using a needle to vent into a balloon. After 15min, the reaction was allowed to warm to room temperature with continued stirring. Upon completion, the reaction was concentrated under reduced pressure; the generated acid chloride was re-dissolved in dry THF to make a 1M solution, and the solution was added slowly to the prepared enolate at-78C. The enolate was prepared by first adding MeOAc (1.05 equiv) to a dry flask charged with a stir bar under nitrogen. The flask was cooled down to-78C to which LHMDS (1M in THF, 2.10 equiv) was added dropwise and stirred for 45minat-78C. The reaction was monitored by TLC until complete conversion of the acid chloride was observed. Upon completion, the reaction was quenched with NH4Cl (aq) at-78C, extracted with EtOAc three times, dried over Na2SO4, and filtered through a celite plug. The combined organic layers were concentrated under reduced pressure and purified by flash chromatography on silica gel using EtOAc/Hexanes as the mobile phase., 5381-25-9

Big data shows that 5381-25-9 is playing an increasingly important role.

Reference£º
Article; Martin, M. Cynthia; Sandridge, Matthew J.; Williams, Corey W.; Francis, Zola A.; France, Stefan; Tetrahedron; vol. 73; 29; (2017); p. 4093 – 4108;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

 

Brief introduction of 5381-25-9

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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.5381-25-9,1-Benzothiophene-3-carboxylic acid,as a common compound, the synthetic route is as follows.

While stirring (1RS,2SR)-2-amino-1-(4-fluorophenyl)-3-[4-(trifluoromethyl)phenyl]propan-1-ol (0.173 g, 0.552 mmol), 1-benzothiophene-3-carboxylic acid (see Synth. Commun., 15, 711-713 (1984)) (0.10 g, 0.55 mmol) and 1-hydroxybenzotriazole hydrate (85 mg, 0.55 mmol) in acetonitrile (10 ml), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.11 g, 0.55 mmol) was added, and the mixture was stirred overnight at room temperature. The reaction solution was diluted with ethyl acetate, washed with aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate and passed through silica gel. The solvent was evaporated under reduced pressure and the obtained residue was crystallized from diethyl ether-hexane to give the objective substance. white crystal yield 0.204 g, 78% mp 188-189C; 1H-NMR (CDCl3, 200MHz) delta 2.88-3.08 (2H, m), 3.64 (1H, d, J = 3.6 Hz), 4.59-4.72 (1H, m), 5.13 (1H, t, J = 3.2 Hz), 6.04 (1H, d, J = 8.8 Hz), 7.09 (2H, t, ! J = 8.8 Hz), 7.31-7.60 (9H, m), 7.82-7.92 (2H, m); IR (KBr) 3333, 1622, 1537, 1510, 1331, 1159, 1123, 1069, 833, 766 cm-1; Anal. Calcd for C25H19F4NO2S: C, 63.42; H, 4.04; N, 2.96. Found: C, 63.50; H, 4.10; N, 2.90.

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Reference£º
Patent; Takeda Chemical Industries, Ltd.; EP1362846; (2003); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem