Simple exploration of 1423-61-6

As the paragraph descriping shows that 1423-61-6 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.1423-61-6,7-Bromobenzo[b]thiophene,as a common compound, the synthetic route is as follows.

Preparation 64; Benzo [b] thiophene-7-carboxaldehyde; Dissolve 7-bromothiophene (5.0 g, 23.5 mmol) in anhydrous tetrahydrofuran (15 mL) under nitrogen and add magnesium metal turnings (712 mg, 29.3 mmol). Stir and warm the reaction to 50C to initiate the Grignard reagent formation. After the exothermic reaction subsides, reflux for 30 minutes. Dilute the solution with tetrahydrofuran (15 ml) and cool to 25C. Add the Grignard reagent dropwise via cannula to a stirred solution of N, N-dimethylformamide (10.2g, 139 mmol) in tetrahydrofuran (25 mL) at-78C under nitrogen. Stir the reaction at 0C for 1 hour and quench with aqueous saturated ammonium chloride. Dilute with diethyl ether, wash with distilled water, and aqueous saturated sodium chloride. Dry the organic phase over anhydrous magnesium sulfate, filter, and concentrate under reduced pressure. Chromatograph on flash silica using a gradient from neat hexane to 50% ethyl acetate in hexane to obtain the title compound as an off-white solid. HRMS : 162. 0138, 1423-61-6

As the paragraph descriping shows that 1423-61-6 is playing an increasingly important role.

Reference£º
Patent; ELI LILLY AND COMPANY; WO2003/76442; (2003); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

 

Simple exploration of 1423-61-6

As the paragraph descriping shows that 1423-61-6 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.1423-61-6,7-Bromobenzo[b]thiophene,as a common compound, the synthetic route is as follows.

A solution of 7-bromobenzo[b]thiophene (6 g, 28.6 mmol) in tetrahydrofuran (60 mL) was cooled to -60 C. Lithium diisopropylamide (2M in THF, 43 mL, 86 mmol) was added dropwise and stirred at -60 C for 1 hour. Then N,N-dimethylformamide (6.3 g, 85.8 mmol) was added and stirred at -60 C for 2 hours. TLC showed the reaction was completed. The reaction was quenched by water and extracted with dichloromethane (30 mL x 3). The combined organic phases were washed with brine, dried over sodium sulfate and concentrated in vacuum. The residue was purified by silica gel column chromatography [petroleum ether/ethyl acetate=15: l ] to afford compound B-110 (5.2 g, 76% yield) as yellow solid. GCMS: M= 241 .9, tR= 10.655., 1423-61-6

As the paragraph descriping shows that 1423-61-6 is playing an increasingly important role.

Reference£º
Patent; FORUM PHARMACEUTICALS, INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; MCRINER, Andrew, J.; WO2015/66371; (2015); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

 

New learning discoveries about 1423-61-6

The synthetic route of 1423-61-6 has been constantly updated, and we look forward to future research findings.

1423-61-6, 7-Bromobenzo[b]thiophene is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Combine 7-bromo-benzo[b] thiophene (426 mg, 2 mmol), bis-(pinacolato)- diboron (756 mg, 3 mmol), Pd(dppf)Cl2 (81 mg, 0.1 mmol), potassium acetate (294 mg, 3 mmol) in dimethyl sulfoxide (DMSO) (10 mL) in a flask. Bubble nitrogen through the mixture for 5 minutes (min). Seal the flask and place it into an oil bath to heat at 100 0C for 4 hours (h). Dilute the mixture with chloroform/isopropyl alcohol (IPA) (3/1). Wash the solution with aqueous saturated sodium chloride. Dry over sodium sulfate. Concentrate the solution in vacuo to a dark residue. Purify by column chromatography (hexane-^ 20 % ethyl acetate in hexane) to give the title compound as a colorless solid (342 mg, 66 %). MS (ES) m/z 261 [M+l]+., 1423-61-6

The synthetic route of 1423-61-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ELI LILLY AND COMPANY; WO2008/144223; (2008); A2;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

 

Downstream synthetic route of 1423-61-6

The synthetic route of 1423-61-6 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.1423-61-6,7-Bromobenzo[b]thiophene,as a common compound, the synthetic route is as follows.

A solution of 6.58 ML (47 MMol) diisopropylamine in 25 ML tetrahydrofuran was cooled to 0C and then 29.4 ML (47 MMol) n-butyllithium (1.6 M in hexanes) were added.. The mixture was allowed to warm to room temperature over 1 hour and was then added dropwise to a mixture of 5.0 gm (24 MMol) 7-bromobenzothiophene and 6.1 ML (47 MMol) trimethylsilyl chloride in 15 ML tetrahydrofuran at -78C. The reaction mixture was stirred for 2 hours and was then poured into ice water.. This mixture was extracted well with diethyl ether.. The combined organic phases were washed with 1N hydrochloric acid, dried over sodium sulfate and concentrated under reduced pressure to provide 6.1 gm (91%) of the title compound., 1423-61-6

The synthetic route of 1423-61-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ELI LILLY AND COMPANY; EP1204660; (2004); B1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

 

Some tips on 1423-61-6

As the paragraph descriping shows that 1423-61-6 is playing an increasingly important role.

1423-61-6, 7-Bromobenzo[b]thiophene is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 1: Methyl 3-(benzothiophen-7-yl)-l-phenyl-pyrazole-5-carboxylate [00171] A suspension of intermediate 2 (3 mL of the solution from step 3, -0.54 mmol), 7-bromobenzothiophene (116 mg, 0.54 mmol), Pd(PPh3)4 (32.1 mg, 28 muiotaetaomicron), caesium fluoride (134 mg, 0.88 mmol) and methanol (1 mL) was stirred in a microwave reactor at 120 C for 30 min. The supernatant was decanted, evaporated to dryness and used immediately., 1423-61-6

As the paragraph descriping shows that 1423-61-6 is playing an increasingly important role.

Reference£º
Patent; CHDI FOUNDATION, INC.; DOMINGUEZ, Celia; MUNOZ-SANJUAN, Ignacio; MAILLARD, Michel; VATER, Huw, D.; JARVIS, Rebecca, E.; LUCKHURST, Christopher, A.; BUeRLI, Roland, W.; WISHART, Grant; STOTT, Andrew, J.; WO2014/159214; (2014); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

 

Downstream synthetic route of 1423-61-6

The synthetic route of 1423-61-6 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.1423-61-6,7-Bromobenzo[b]thiophene,as a common compound, the synthetic route is as follows.

i) 4-Benzo[b]thiophen-7-yl-pyridine This compound was prepared in analogy to the procedure described in Example 16i) starting from 7-bromo-benzo[b]thiophene (Focus synthesis, CAS:1423-61-6) using 4-pyridineboronic acid as reagent to obtain 4-benzo[b]thiophen-7-yl-pyridine as a grey solid. MS (ISP): m/e 212.1 (M+H)+

The synthetic route of 1423-61-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Hebeisen, Paul; Kitas, Eric A.; Minder, Rudolf E.; Mohr, Peter; Wessel, Hans Peter; US2009/143448; (2009); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

 

Analyzing the synthesis route of 1423-61-6

1423-61-6 7-Bromobenzo[b]thiophene 12045538, abenzothiophene compound, is more and more widely used in various.

1423-61-6, 7-Bromobenzo[b]thiophene is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Preparation 24; 4-Benzo[?]thiophen-7-yl-3-methoxymethoxy-pyridine; Solution A: Treat a solution of 3 -methoxymethoxy -pyridine (2.5 g, 18 mmol) in diethyl ether (90 mL) at -70 0C with tert-butyl lithium (1.7 M in pentane, 10 mL, 18 mmol) dropwise over 10 min. Stir the mixture at -70 0C for 40 min and add a solution of -14-triisopropyl borate (5 mL, 22 mmol) in THF (10 mL) dropwise over 5 min. Stir the mixture at -70 0C for one hour and then remove the ice bath and allow the mixture to slowly warm to room temperature.Solution B: Treat a solution of 7-bromo-benzo[]thiophene (3.8 g, 18 mmol), 2- (di-tert-butylphosphino)biphenyl (268 mg, 0.90 mmol), [1,1 ‘- bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (1 : 1) (732 mg, 0.90 mmol) in 1,4-dioxane (30 mL) with 2 M aqueous sodium carbonate (72 mL, 36 mmol). Once solution A reaches room temperature, heat the solution to 80 0C. Treat solution B with solution A dropwise over 10 min. Heat the combined solution to 85 0C for 5 hours. Cool the mixture to room temperature and dilute with ethyl acetate and water. Wash the organic phase with water and saturated aqueous sodium chloride, dry over sodium sulfate, filter, and concentrate in vacuo. Purify the crude product by column chromatography on 120 g silica gel eluting with a gradient of dichloromethane to ethyl acetate to give the title compound (3.8 g) containing some starting 3 -methoxymethoxy -pyridine. Use product without further purification. 1H NMR (400 MHz, CDCl3) delta 8.68 (s, IH), 8.42 (d, J= 4 Hz, IH), 7.88 (d, J= 8 Hz, IH), 7.33- 7.50 (m, 5H), 5.12 (s, 2H), 3.36 (s, 3H).

1423-61-6 7-Bromobenzo[b]thiophene 12045538, abenzothiophene compound, is more and more widely used in various.

Reference£º
Patent; ELI LILLY AND COMPANY; WO2008/76704; (2008); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

 

Brief introduction of 1423-61-6

1423-61-6 7-Bromobenzo[b]thiophene 12045538, abenzothiophene compound, is more and more widely used in various.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1423-61-6,7-Bromobenzo[b]thiophene,as a common compound, the synthetic route is as follows.

Preparation 12-Benzo[b]thiophen-7-yl-4,4,5,5-tetramethyl-[l,3,2]dioxaborolane Combine 7-bromo-benzo[b]thiophene (426 mg, 2 mmol), bis(pinacolato)diboron (756 mg, 3 mmol), Pd(dppf)Cl2 (81 mg, 0.1 mmol), and potassium acetate (294 mg, 3 mmol) in dimethylsulfoxide (DMSO) (10 mL) in a flask. Bubble nitrogen through the mixture for 5 min. Seal the flask and put it into an oil bath and heat to 100 0C for 4 hours (h). Dilute the mixture with chloroform/is opropyl alcohol (IPA) (3/1). Wash the solution with saturated aqueous sodium chloride. Dry over sodium sulfate. Concentrate the solution in vacuo to a dark residue. Purify by column chromatography (hexane-^ 20 % ethyl acetate in hexane) to afford the title compound as a colorless solid (342 mg, 66 %). MS (ES) m/z 261 [M+ 1]+.

1423-61-6 7-Bromobenzo[b]thiophene 12045538, abenzothiophene compound, is more and more widely used in various.

Reference£º
Patent; ELI LILLY AND COMPANY; WO2008/144222; (2008); A2;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

 

New learning discoveries about 1423-61-6

The synthetic route of 1423-61-6 has been constantly updated, and we look forward to future research findings.

1423-61-6, 7-Bromobenzo[b]thiophene is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Under a nitrogen stream, 12.2 g (35.2 mmol) of 7-bromobenzo [b] thiophene,6.44 g (38.7 mmol) of 2-nitrophenylboronic acid,4.22 g (105.6 mmol) of NaOH and 300 ml / 150 ml of THF / H2O were added and stirred. 2.03 g (5 mol%) of Pd (PPh3) 4 was added at 40 deg. CFollowed by stirring at 80 C for 12 hours.After completion of the reaction, the mixture was extracted with methylene chloride, and the mixture was filtered through MgSO4.After removing the solvent of the filtered organic layer, the residue was purified by column chromatography 7.38 g (28.9 mmol, yield 82%) of 7- (2-nitrophenyl) benzo [b] thiophene were obtained.

The synthetic route of 1423-61-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Doosan Co., Ltd; Kim Hoe-mun; Kim Seong-mu; Kim Yeong-bae; Kim Tae-hyeong; Park Ho-cheol; Lee Chang-jun; Baek Yeong-mi; Shin Jin-yong; (188 pag.)KR101879905; (2018); B1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

 

Analyzing the synthesis route of 1423-61-6

1423-61-6 7-Bromobenzo[b]thiophene 12045538, abenzothiophene compound, is more and more widely used in various.

1423-61-6, 7-Bromobenzo[b]thiophene is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Preparation 108A: 5-(Benzo[b]thiophen-7-yl)-4-methylpyrimidine[00353] A vessel capable of sealing was charged with a mixture of 7- bromobenzo[b]thiophene (100 mg, 0.467 mmol), 4-methylpyrimidin-5-ylboronic acid (97 mg, 0.70 mmol), PdCl2(dppf)-CH2Ci2 adduct (19.2 mg, 0.023 mmol), dioxane (3 mL), and a 2.0 M water solution of K3PO4 (0.7 mL, 1.41 mmol) and was purged with nitrogen for 10 min. The vessel was sealed and heated at 100 C for 16 hours. Upon cooling, the reaction mixture was diluted with CH2CI2 and filtered with CH2Cl2/MeOH washing. The filtrate was concentrated under reduced pressure. The residue was dissolved in CH2CI2 and washed with water, brine, dried over anhydrous Na2S04 and concentrated under reduced pressure. The crude material was purified by BIOTAGE eluting with 0%-15% EtOAc/CH2Cl2 at 30 mL/min. Concentration of appropriate fractions provided the title compound (32 mg, 30% yield). LC/MS: Example 108A (at) 2.49 min (RT) (Condition G). MS (ES): m/z=227.07.1 [M+H]+. ? NMR (400 MHz, CDC13) delta ppm 9.19 (1 hr, s), 8.68 (1 hr, s), 7.92 (1 hr, d, J=8.06 Hz), 7.38-7.52 (3 hr, m), 7.23 (1 hr, d, J=7.05 Hz), 2.44 (3 hr, s).

1423-61-6 7-Bromobenzo[b]thiophene 12045538, abenzothiophene compound, is more and more widely used in various.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; BALOG, James Aaron; HUANG, Audris; VELAPARTHI, Upender; LIU, Peiying; WO2013/49263; (2013); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem