Category: 1423-61-6

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.

To a solution of 7-bromobenzo[b]thiophene (5.0 g, 24 mmol) in diethyl ether (50 mL) at 100 C under nitrogen was added dropwise t-BuLi (1.3 mol/L, 55 mL). The mixture was stirred at – 100 C for 15 min, and dry acetone (3.6 g, 48 mmol) was added dropwise at -100 C. The mixture was stirred at -100 C for 2 hours. TLC showed the reaction was complete and the formation of two products (about 1 : 1). The reaction mixture was quenched with saturated aqueous ammonium chloride (20 mL) dropwise at 0 C, and then extracted with ethyl acetate (3 x 50 mL). The combined organic layers were washed with brine (2 chi 50 mL), dried over anhydrous sodium sulfate, concentrated in vacuo and purified by silica gel column chromatography [petroleum ether: ethyl acetate = 40: 1] to give compound B-302 (0.80 g, 34% yield, the lower spot on TLC) as a yellow oil.

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; FORUM PHARMACEUTICALS, INC.; ACHARYA, Raksha; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; COOK, Andrew, Simon; HARRISON, Bryce, Alden; KOENIG, Gerhard; MCRINER, Andrew, J.; (400 pag.)WO2016/100184; (2016); 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

Preparation 2; Benzo[/?]thiophene-7-boronic acid; Combine 7-bromobenzo[?]thiophene (300 g, 1.41 mmol) and triisopropylborate (403.6 g, 2.15 mmol) in anhydrous tetrahydrofuran (THF) (4000 mL) 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 hour. Remove the cooling bath and slowly add 4 L of water. Next, add concentrated HCl (75 mL) until the pH of the solution is about pH=2. Allow the slurry to stir for 1 hour. Add sufficient 5 N aqueous NaOH to adjust the pH of the mixture to about pH=12. Separate the layers and save the aqueous layer. Dilute the organic layer with 4 L of methyl-tert-butyl ether and extract with 1 L of 5 N aqueous NaOH. Separate the layers. Combine the aqueous layer with the previous aqueous extract. Wash the aqueous layer with additional methyl-tert-butyl ether (4 L). Separate the layers and transfer the aqueous layers 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 min and 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. Remove the yellow color by slurrying the dried solid with 2 L of w-heptane for 30 min. Again filter off the solid, air-dry for 30 min, and vacuum dry at 40 0C overnight to afford 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, As the paragraph descriping shows that 1423-61-6 is playing an increasingly important role.

Reference£º
Patent; ELI LILLY AND COMPANY; WO2008/76705; (2008); 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

To a stirring solution of diisopropylamine (2.374 g, 23.46 mmol) in THF (12 mL) at -70 C under nitrogen was added butyllithium (8.26 mL, 20.65 mmol, 2.5M solution in hexanes). After 15 minutes at -70 C was added 7- bromo-l-benzothiophene (4.0 g, 18.77 mmol, Intermediate X13) in THF (10 mL). The cooling bath was removed and reaction warmed to -30 C then returned to -70 C. To the colorless solution was added di-tert-butyl (6-((E)- (((S)-tert-butylsulfinyl)imino)methyl)-5-chloro-2-pyridinyl)imidodicarbonate (8.63 g, 18.77 mmol, Intermediate AA4) in THF (15 mL) at a rate not to exceed – 60 C. After 18 h of warming to 20 C, the reaction was quenched with sat. NH4C1 (20 mL). The reaction was then partitioned between EtOAc (120 mL) and sat NH4C1 (50 mL). The organic was the dried over MgS04, concentrated onto dry silica (30 g) under reduced pressure, then purified by silica gel chromatography (330 g) eluting products with 10 to 50% EtOAc in hexanes to afford tert-butyl (6-((7-bromo-l-benzothiophen-2-yl)(((S)-tert- butylsulfinyl)amino)methyl)-5-chloro-2-pyridinyl)carbamate (6.0 g) as a white solid., 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; AMGEN INC.; ASHTON, Kate; BARTBERGER, Michael D.; BOURBEAU, Matthew Paul; CROGHAN, Michael D.; FOTSCH, Christopher H.; HUNGATE, Randall W.; KONG, Ke; NISHIMURA, Nobuko; NORMAN, Mark H.; PENNINGTON, Lewis D.; REICHELT, Andreas; SIEGMUND, Aaron C.; TADESSE, Seifu; ST. JEAN, David Jr; YANG, Kevin C.; YAO, Guomin; WO2013/173382; (2013); A1;,
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.

To a 2-L three-necked round-bottomed flask containing a solution of 7-bromo-l-benzothiophene (50 g, 236 mmol, Intermediate XI 3) in THF (400 mL) at -78 C was added LDA (236 mL of a 1.8 M solution in THF, 472 mmol, Sigma- Aldrich, India) and the mixture was stirred at -78 C for 45 min. A solution of N-((S,E)-(2-chlorophenyl)methylidene)-2-methyl-2- propanesulfinamide (57.3 g, 236 mmol, Intermediate Yl) in THF (100 mL) was added dropwise and the mixture was stirred at -78 C for 16 h. Water (500 mL) was added, the mixture was allowed to warm to room temperature, and was extracted with EtOAc (2 x 500 mL and 2 x 200 mL). The combined organic layers were dried (Na2S04), filtered, and concentrated under reduced pressure. The resulting product was purified by column chromatography (basic alumina, 0% to 10% EtOAc/hexane to deliver (S)-N-((R)-(7-bromo-l-benzothiophen-2- yl)(2-chlorophenyl)methyl)-2-methyl-2-propanesulfinamide (25 g) as a pale- yellow liquid.

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

Reference£º
Patent; AMGEN INC.; ASHTON, Kate; BARTBERGER, Michael D.; BOURBEAU, Matthew Paul; CROGHAN, Michael D.; FOTSCH, Christopher H.; HUNGATE, Randall W.; KONG, Ke; NISHIMURA, Nobuko; NORMAN, Mark H.; PENNINGTON, Lewis D.; REICHELT, Andreas; SIEGMUND, Aaron C.; TADESSE, Seifu; ST. JEAN, David Jr; YANG, Kevin C.; YAO, Guomin; WO2013/173382; (2013); A1;,
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.

To a stirring solution of diisopropylamine (0.594 g, 5.87 mmol) in THF (3 mL) at -70 C under nitrogen was added n-butyllithium, 2.5 M solution in hexanes (2.065 mL, 5.16 mmol) at a rate not to exceed -60 C. After 15 min a solution of 7-bromo-l-benzothiophene (Maybridge Chemical Co., Ltd., 1.0 g, 4.69 mmol) in THF (4 mL) was added dropwise at a rate that did not exceed an internal temperature of -65 C. This solution was stirred for 1 h at -75 C. To this was added a solution of N-((lE)-(2- chlorophenyl)methylidene)cyclopropanesulfonamide (1.144 g, 4.69 mmol, Intermediate AAIO) in THF (4 mL) at a rate that did not exceed an internal temperature of -65 C. After 15 min, the reaction was warmed to -30 C then quenched with saturated NH4C1 (20 mL). To the biphasic solution was added EtO Ac (20 mL). The isolated organic was then dried over MgS04, filtered, concentrated under reduced pressure, then purified by silica gel chromatography (80 g) eluting products with 0 to 30% gradient of EtO Ac/Hex to afford N-((7- bromo-l-benzothiophen-2-yl)(2-chlorophenyl)methyl)cyclopropanesulfonamide (0.71 g, 1.554 mmol, 33.1 % yield) as colorless oil (mixture of 2 enantiomers).

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; AMGEN INC.; ASHTON, Kate; BARTBERGER, Michael D.; BOURBEAU, Matthew Paul; CROGHAN, Michael D.; FOTSCH, Christopher H.; HUNGATE, Randall W.; KONG, Ke; NISHIMURA, Nobuko; NORMAN, Mark H.; PENNINGTON, Lewis D.; REICHELT, Andreas; SIEGMUND, Aaron C.; TADESSE, Seifu; ST. JEAN, David Jr; YANG, Kevin C.; YAO, Guomin; WO2013/173382; (2013); 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

In some embodiments (Scheme 3), in a 50 mL round-bottom flask, 7-bromo- benzo[Z?]thiophene (0.213 g,l mmol) and Pd(PPh3)4 (0.116 g, 0.1 mmol) are suspended in THF (3 mL), then zinc reagent (6 mL, 3 mmol) is added with syringe. The reaction is stirred at 60 C for three hours, then the reaction mixture is cooled to room temperature, solvent is removed, EtOAc (30 mL) is added, and the mixture washed with 2 N NaOH solution (20 mL x 2). The organic layer is dried with Na2S04 and concentrated. The crude product is purified by ISCO silica column using 0-25% EtOAc in hexanes to yield 49 mg (20.9% yield) desired product methyl (2S)-3-(l- benzothiophen-7-yl)-2-methylpropanoate. NMR. (499 MHz, CDC13) delta 7.70 (dd, J= 7.9, 1.1 Hz, 1H), 7.43 (d,J=5.4Hz, 1H), 7.36 (d,J= 5.4 Hz, 1H), 7.31 (t,J=7.6 Hz, 1H), 7.15 (d, J= 7.2 Hz, 1H), 3.66 (s, 3H), 3.35(dd,J = 13.9, 6.8 Hz, 1H), 3.12 – 3.00 (m, 1H), 2.93 (dd,J= 14.0,8.0 Hz, 1H), 1.21 (d,J=7.0Hz, 3H).

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

Reference£º
Patent; RIDEOUT, Darryl; LEDERMAN, Seth; DAUGHERTY, Bruce; GERSHELL, Leland, J.; (643 pag.)WO2016/105448; (2016); 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

General procedure: To a 10 mL round-bottom flask were added Cat.III (3.2 mg, 0.005 mmol, 2 mol %), Ag2O (116 mg, 0.5 mmol, 2 equiv), benzoquinone (14 mg, 0.125 mmol, 0.5 equiv), Cs(tfa) (64 mg, 0.25 mmol, 1 equiv.), benzothiophene/benzofurans (0.25 mmol, 1 equiv), aryl MIDA boronate ( 0.375 mmol, 1.5 equiv), and 15% H2O and 2% CF3SO3H of TFA (1 mL). The reaction mixture was stirred at 30-50 C for 20 h. The suspension was cooled to room temperature and extracted with dichloromethane (3 ¡Á 10 mL). The combined organic layers were washed with 20% aqueous NaHCO3 solution (40 mL). After evaporation of the solvent the crude product was purified by chromatography on silica gel to give the desired product., 1423-61-6

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

Reference£º
Article; Wang, Zhiwei; Li, Yabo; Yan, Beiqi; Huang, Mengmeng; Wu, Yangjie; Synlett; vol. 26; 4; (2015); p. 531 – 536;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem