Category: 1423-61-6

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[?]thiophene (6.53 g, 30.64 mmol), 5-fluoro-2- hydroxy phenyl boronic acid (4.87 g, 31.26 mmol), Pd(dppf)Cl2 (1.25 g, 1.53 mmol), 2-(di-tert-butylphosphino)biphenyl (0.28 g, 0.92 mmol), sodium carbonate (2 M, 30.64 mL, 61.92 mmol) in dioxane (60 mL, alternative THF) in a flask. Heat the mixture at 100 0C for 2 h. Dilute the mixture with chloroform/IPA (3/1). Wash the solution with aqueous saturated sodium chloride. Dry over sodium sulfate. Concentrate the solution in vacuo . Purify the residue by column chromatography (hexane to 10 % ethyl acetate in hexane) to give the title compound (6.0 g, 80 %) as a yellow solid. MS (ES) m/z 243 [M-I]+.

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

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 commercially available 7-bromobenzo[b]thiophene (8.0 g, 37.5 mmol) in ether (50.0 mL) was cooled to -78 C was and treated dropwise with BuLi (1.6 M solution in Hexanes, 21 mL, 37.5 mmol) and stirred at -78 C for 20 min. The reaction mixture was treated with DMF (5.4 g, 67.4 mmol) and stirred at -78 C for 1 h. The reaction mixture was diluted with water and extracted with ether. The combined organic layer were washed with water, dried (MgSO4) filtered concentrated in vacuo and purified by chromatography (SiO2, EtOAc/Hexanes) to yield 5 as a colorless oil. 1H NMR (400 MHz, CDCl3) delta 10.25 (s, 1H), 8.12 (d, 1 H, J = 7.6 Hz), 7.90 (d, 1H, J = 7.2 Hz), 7.67 (d, 1H, J = 5.6 Hz), 7.59 (t, 1H, J = 7.6 Hz), 7.45 (d, 1H, J = 5.6 Hz)., 1423-61-6

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

Reference£º
Article; Venkatraman, Srikanth; Velazquez, Francisco; Gavalas, Stephen; Wu, Wanli; Chen, Kevin X.; Nair, Anilkumar G.; Bennett, Frank; Huang, Yuhua; Pinto, Patrick; Jiang, Yueheng; Selyutin, Oleg; Vibulbhan, Bancha; Zeng, Qingbei; Lesburg, Charles; Duca, Jose; Huang, Hsueh-Cheng; Agrawal, Sony; Jiang, Chuan-Kui; Ferrari, Eric; Li, Cheng; Kozlowski, Joseph; Rosenblum, Stuart; Shih, Neng-Yang; Njoroge, F. George; Bioorganic and Medicinal Chemistry; vol. 21; 7; (2013); p. 2007 – 2017;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

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[?]thiophene (6.53 g, 30.64 mmol), 5-fluoro-2- hydroxy phenyl boronic acid (4.87 g, 31.26 mmol), Pd(dppf)Cl2 (1.25 g, 1.53 mmol), 2-(di-tert-butylphosphino)biphenyl (0.28 g, 0.92 mmol), sodium carbonate (2 M, 30.64 mL, 61.92 mmol) in dioxane (60 mL, alternative THF) in a flask. Heat the mixture at 100 0C for 2 h. Dilute the mixture with chloroform/IPA (3/1). Wash the solution with aqueous saturated sodium chloride. Dry over sodium sulfate. Concentrate the solution in vacuo . Purify the residue by column chromatography (hexane to 10 % ethyl acetate in hexane) to give the title compound (6.0 g, 80 %) as a yellow solid. MS (ES) m/z 243 [M-I]+.

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

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

Scheme I, step C: To magnesium turnings (703 mg, 0.0289 mole) in 10 mL anhydrous tetrahydrofuran was added part of a solution of of 7-bromobenzothiophene (6.16 g, 0.0289 mole) in 30 mL anhydrous tetrahydrofuran. The mixture was brought to reflux and when the grignard reaction started, foaming was controlled by removing the heating mantle. The balance of the benzothiophene solution was added at a rate to maintain gentle reflux and then refluxed an additional hour. The reaction was cooled to 25 C. and of N-boc-3-pyrrolidone (5.34 g, 0.0289 mole) in 20 mL anhydrous tetrahydrofuran was added. The reaction was refluxed 1 hr and then stirred at room temperature overnight. The reaction was cooled in an ice bath and add dropwise saturated ammonium chloride solution until a granular precipitate was formed. The precipitate was filtered and rinsed with additional tetrahydrofuran. Evaporation gave 9.9 g of crude material as an oil which was flashed chromatographed over silica gel. Elution with 20% ethyl acetate in hexane provided the title compound (1.004 g, 11%) as a white foam. Mass Spec ESI+, M+1=320.2 (MW=319.4) 1H NMR (300 MHz, CDCl3) delta 1.48 (9H, s); 2.17 to 2.23 (3H, m); 3.71 to 3.94 (4H, m); 7.33 to 7.81 (5H, m).

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; US6353008; (2002); B1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

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.,1423-61-6

Under Ar atmosphere, to a mixture of 7-bromo-benzo[b]thiophene (40 g, 0.19 mol) and Zn(CN)2 (16 g, 0.132 mol) were added Pd(PPh3)4 (10 g) and DMF (800 mL) and the mixture was stirred at 90 0C -100 0C for 3 h. The reaction solution was cooled to room temperature (30 0C) and filtered. The filtrate was concentrated under reduced pressure. The residue was taken up with EtOAc (1000 mL) and saturated aq. NaHCO3 (500 mL) and then filtered. The filtrate layers were separated. The organic layer was washed with brine, dried over Na2SO4 and concentrated to give a crude product, which was purified by column chromatography (silica, elute; PE to EtOAc_PE=l:30) to afford the title compound (24 g, 80 %) as a white solid.

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

Reference£º
Patent; TARGEGEN INC.; WO2009/49028; (2009); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

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, of 12.2g (35.2mmol) 7-bromobenzo [b] thiophene, 6.44g of (38.7mmol) 2- nitrophenyl boronic acid, and NaOH of 4.22g (105.6mmol), 300ml / was stirred into a THF / H2O of 150ml. 40 put the Pd (PPh3) 4 of 2.03g (5mol%) in, and the mixture was stirred for 12 hours at 80 . After completion of the reaction, and extracted with methylene chloride, put MgSO4, and filtered. After removal of the solvent of the filtered organic layer, was obtained by column chromatography 7- (2-nitrophenyl) benzo [b] thiophene 7.38 g (28.9 mmol, 82% yield)., 1423-61-6

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

Reference£º
Patent; DOOSAN CORPORATION; KIM, TAE HYUNG; LEE, IN HYUK; KIM, HOE MOON; SHIN, JIN YONG; PARK, HO CHEOL; LEE, CHANG JUN; BEAK, YOUNG MI; LEE, EUN JUNG; (96 pag.)JP2015/527347; (2015); A;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

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 1064-Benzo[b]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 triisopropyl borate (5 mL, 22 mmol) in THF (10 mL) dropwise over 5 min. Stir the mixture at -70 0C for 1 h and then remove the ice bath and allow the mixture to slowly warm to RT. Solution B: Treat a solution of 7-bromo-benzo[b]thiophene (3.8 g, 18 mmol), 2- (di-tert-butylphosphino)biphenyl (268 mg, 0.90 mmol), Pd(dppf)Cl2 (732 mg, 0.90 mmol) in 1,4-dioxane (30 mL) with 2 M aqueous sodium carbonate (72 mL, 36 mmol). Heat the solution to 80 0C once solution A reaches RT. Treat solution B with solution A dropwise over 10 min. Heat the combined solution to 85 0C for 5 h. Cool the mixture to RT and dilute with ethyl acetate and water. Wash the organic phase with water and aqueous saturated sodium chloride, dry over sodium sulfate, filter, and concentrate in vacuo. Purify the residue by column chromatography on 12O g silica gel eluting with a gradient of DCM to ethyl acetate to give the title compound (3.8 g) containing some starting 3-methoxymethoxy-pyridine. 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

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

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

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.

Combine 7-bromobenzo[b]thiophene (300 g, 1.41 mmol) and tri- isopropylborate (403.6 g, 2.15 mmol) in anhydrous THF (4 L) in a 12-L Morton flask fitted with a mechanical stirrer and cool under nitrogen in a dry-ice/acetone bath to – 70 0C. Add M-butyl lithium (1.6 M in hexane, 714 g, 1.68 mmol) dropwise at such a rate as to keep the internal temperature less than -67.5 0C. After the addition is complete allow the reaction mixture to stir at this temperature for 1 h. Remove the cooling bath and slowly add 4 L of water, which causes the temperature to rise to about -5 0C. Next, add concentrated HCl (75 mL) until the pH of the solution is about pH = 2. Allow the slurry to stir for 1 h. Add sufficient 5 N aqueous NaOH to adjust the pH of the mixture to about pH = 12 and transfer to a 22-L bottom-drop funnel. Separate and save the lower aqueous layer. Dilute the upper organic layer with 4 L of methyl-tert-butyl ether and extract with 1 L of 5 N aqueous NaOH. Separate the aqueous layer, combine with the previous aqueous extract and place back in the separatory funnel. Wash the aqueous layer with additional methyl-tert-butyl ether (4 L). Again, separate the aqueous layer and transfer to a 12-L, 3 -neck round bottom flask fitted with a mechanical stirrer. Cool the solution to +5 0C with an ice-water bath. Add concentrated HCl slowly until the pH of the solution is about pH = 2. Stir the mixture for 30 minutes and then filter off the resulting solid. Rinse the solid on the funnel twice with 2 L of water and allow to air-dry for 30 min. Place the solid in a vacuum oven at 50 0C and dry under vacuum overnight. The dried solid is slurried with 2 L of M-heptane for 30 min to remove the yellow color. Again filter off the solid, air-dry for 30 min and then vacuum-dry at 40 0C overnight to give the title compound (188.8 g, 75 %) as a white solid. 1H NMR (400 MHz, CD3OD) delta 7.86 (d, J= 8 Hz, IH), 7.49-7.57 (m, 2H), 7.30-7.39 (m, 2H)., 1423-61-6

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

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

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.

Scheme II, step C: 7-bromobenzo(b)thiophene (0.25 g, 1.17 mmol) and 1-(t-butoxycarbonyl)-3-hydroxy-3-tributylstannyl-2-pyrroline (1.17 mmol, prepared in Scheme II, step B above), 2,6-di-tert-butyl-4-methylphenol (25 mg) and tetrakis(triphenylphosphine)palladium(0) (0.046 g, 0.04 mmol) are combined in toluene (10 mL). The reaction mixture is heated to reflux for 16 hours. It is then cooled, filtered and concentrated under vacuum. The residue is purified by flash chromatography (5% ethyl acetate/hexane, silica gel) to provide the title compound., 1423-61-6

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

Reference£º
Patent; Eli Lilly and Company; US6353008; (2002); B1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

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

[0169] Under Ar atmosphere, to a mixture of 7-bromo-benzo[b]thiophene (40 g, 0.19 mol) and Zn(CN)2 (16 g, 0.132 mol) were added Pd(PPh3)4 (10 g) and DMF (800 mL) and the mixture was stirred at 90 0C -100 0C for 3 h. The reaction solution was cooled to room temperature (30 0C) and filtered. The filtrate was concentrated under reduced pressure. The residue was taken up with EtOAc (1000 mL) and saturated aq. NaHCO3 (500 mL) and then filtered. The filtrate layers were separated. The organic layer was washed with brine, dried over Na2SO4 and concentrated to give a crude product, which was purified by column chromatography (silica, elute; PE to EtOAc_PE=l:30) to afford the title compound (24 g, 80 %) as a white solid.

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

Reference£º
Patent; TARGEGEN INC.; WO2009/26345; (2009); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem