Some tips on 4923-87-9

The synthetic route of 4923-87-9 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.4923-87-9,5-Bromobenzothiophene,as a common compound, the synthetic route is as follows.

A solution of 5-bromobenzo[b]thiophene (LXVII) (1.2 g, 6 mmol), zinc cyanide (0.66 g, 6 mmol) and tetrakis(triphenylphosphorus)palladium (0) (0.65 g, 0.6 mmol) in dry DMF (10 mL) was stirred at reflux under nitrogen atmosphere for 1 h. The mixture was poured into cold water and extracted with EtOAc (3¡Á). The combined organic layers were concentrated in vacuum to give the crude benzo[b]thiophene-5-carbonitrile (LXVIII) as a white solid. (0.90 g, 6 mmol, 100%) ESIMS found C9H5NS m/z 160.0 (M+H).

The synthetic route of 4923-87-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Kumar KC, Sunil; Wallace, David Mark; Hood, John; Barroga, Charlene F.; US2014/243349; (2014); A1;,
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Benzothiophene | C8H6S – PubChem

 

Brief introduction of 4923-87-9

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4923-87-9, 5-Bromobenzothiophene is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: Aryl halide (0.5 mmol), alpha-Iminonitrile (0.6 mmol), Cu(TFA)2 (1.0 mmol), Pd(OAc)2(0.1 mmol) and 2ml DMF were added into a 15 ml sealed tube with a magneticstirring bar. Stirred under air at 120C for 24 h. Monitor the reaction by TLC. Themixture was poured into water (10 ml) and extracted by ethyl acetate (3¡Á10 ml).Dried by Na2SO4 and evaporated. Finally, pure the mixture by silica gel column.

As the paragraph descriping shows that 4923-87-9 is playing an increasingly important role.

Reference£º
Article; Shi, Yu-Long; Yuan, Qing; Chen, Zhen-Bang; Zhang, Fang-Ling; Liu, Kui; Zhu, Yong-Ming; Synlett; vol. 29; 3; (2018); p. 359 – 363;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

 

Downstream synthetic route of 4923-87-9

4923-87-9 5-Bromobenzothiophene 2776578, abenzothiophene compound, is more and more widely used in various.

4923-87-9, 5-Bromobenzothiophene is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Dissolve 5-bromo-benzo [b] thiophene (J. Mater. Chem., 10: 2069-2081,2000 ; 49 g, 7.0 mmol) in DMSO (40 mL). Add bis (pinacolato) diboron (7 mmol), PdCl2 (dppf)-CH2Cl2 (0.33 mmol), and KOAc (20 mmol). Flush the flask with N2, and then heat the reaction mixture to 80C with stirring. Continue to heat the reaction mixture for 3 hours, and then cool to room temperature. Add water (66 mL) and extract the aqueous layer with EtOAc (3 x 66 mL). Combine the organic layers and dry with Na2SO4, filter, concentrate and purify by flash column chromatography (silica gel, 0-5% Et20/pentane) to give 1.56 g of the title compound (86%).

4923-87-9 5-Bromobenzothiophene 2776578, abenzothiophene compound, is more and more widely used in various.

Reference£º
Patent; ELI LILLY AND COMPANY; WO2004/9086; (2004); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

 

Downstream synthetic route of 4923-87-9

4923-87-9 5-Bromobenzothiophene 2776578, abenzothiophene compound, is more and more widely used in various.

4923-87-9, 5-Bromobenzothiophene is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

(A) To a cooled (-10 qC to 5 C) solution of diisopropylamine (422 g, 4.17 mol) in anhydrous THF (4.0 L) was added n-butyllithium (1517 mL of 2.5 M in hexane, 3.79 mol) in drop-wise fashion over a period of 1.5 h under an inert atmosphere of nitrogen. Upon completion of the addition, the reaction solution was stirred at -10 C to 0 C for an additional 30 min, and then cooled to -78 C. A solution of 5-bromobenzo[b]thiophene (670 g, 3.16 mol) and TMSCl (512 g, 4.74 mol) in THF (3.4 L) was added in drop-wise fashion and the resulting reaction mixture was stirred at -78 C. After completion of the reaction, as judged by HPLC analysis, aq. NH4Cl solution (5% w/w, 2 L) was added in drop-wise fashion into the reaction mixture while still under a nitrogen atmosphere and maintaining a temperature between -78 qC and -65 C. The mixture was then allowed to warm to rt and the aqueous phase was removed. Water (2 L) was added to the organic phase and after stirring at room temperature for 15 min, the aqueous phase was removed. The combined aqueous layers were back-extracted with EtOAc (2 L), and the combined organic extracts were washed with sat.d aq. NaCl (2 L), dried (Na2SO4) and concentrated under reduced pressure to provide (5-bromobenzo[b]thiophen-2-yl)trimethylsilane (867 g, purity: 90.0 LCAP) as a light yellow liquid. 1H NMR (CDCl3) 7.93 (d, J = 1.5 Hz, 1H), 7.72 (d, J = 8.4 Hz, 1H), 7.39 (d, J = 8.4 Hz, 1H), 7.36 (s, 1H), 0.37 (s, 9H); LC/MS (APCI+) m/z 283.9 [M]+.

4923-87-9 5-Bromobenzothiophene 2776578, abenzothiophene compound, is more and more widely used in various.

Reference£º
Patent; JANSSEN PHARMACEUTICA NV; KUO, Gee-Hong; PLAYER, Mark R.; YANG, Shyh-Ming; ZHANG, Yue-Mie; HUANG, Hui; (260 pag.)WO2016/57731; (2016); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

 

Downstream synthetic route of 4923-87-9

4923-87-9 5-Bromobenzothiophene 2776578, abenzothiophene compound, is more and more widely used in various.

4923-87-9, 5-Bromobenzothiophene is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

5-bromobenzo[b]thiophene (3.0 g, 14.08 mmol) and 4-hydroxyphenylboronic acid (2.91 g, 21.11 mmol) were dissolved in DME 40 mL. Water 10 mL was added thereto. Pd(dbpf)Cl2 (459 mg, 0.70 mmol) and Cs2CO3 (13.68 g, 42.24 mmol) were added thereto, and refluxed with heating at 90 C. for a day. The reaction mixture was filtered through Celite. The obtained filtrate was extracted with EtOAc three times, dried over MgSO4, and then concentrated under reduced pressure. The obtained concentrate was purified by silica gel column chromatography (15-20% EtOAchexane) to yield the title compound as white solid (2.30 g, 72%)

4923-87-9 5-Bromobenzothiophene 2776578, abenzothiophene compound, is more and more widely used in various.

Reference£º
Patent; CHONG KUN DANG PHARMACEUTICAL CORP.; Lee, ChangSik; Jang, TaegSu; Choi, DaeKyu; Ko, MooSung; Kim, DoHoon; Kim, SoYoung; Min, JaeKi; Kim, WooSik; Lim, YoungTae; US2015/166480; (2015); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

Downstream synthetic route of 4923-87-9

4923-87-9 5-Bromobenzothiophene 2776578, abenzothiophene compound, is more and more widely used in various.

4923-87-9, 5-Bromobenzothiophene is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 1 To a solution of 6-bromobenzothiophene (10.0 g, 0.047 mol) and AcCl (4.43 g, 4.0 ml, 0.056 mol) in 1,2-dichloroethane (200 mL) was added SnCl4 (1.0 M/heptane, 56 mL) at 0 C. The mixture was allowed to reach RT and then stirred for 20 h. The mixture was poured onto ice/H2O and extracted with DCM. The organic layer was washed with sat. aqueous NaHCO3, dried and concentrated. Flash chromatography (EtOAc/hexanes, 1:9 then 1:4) afforded 6A (5.6 g).

4923-87-9 5-Bromobenzothiophene 2776578, abenzothiophene compound, is more and more widely used in various.

Reference£º
Patent; SCHERING CORPORATION AND PHARMACOPEIA, LLC; PHARMACOPEIA, INC.; US2010/197562; (2010); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

New learning discoveries about 4923-87-9

4923-87-9 5-Bromobenzothiophene 2776578, 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.4923-87-9,5-Bromobenzothiophene,as a common compound, the synthetic route is as follows.

In a 100 mL screwcapped vessel 5-bromobenzo[b]thiophene (2.30 g, 10.8 mmol) was dissolved in acetone (46 ml). Oxone, monopersulfate (potassium peroxymonosulfate) (27.0 g, 43.2 mmol) and water were added and stirred at 70 C overnight. To the reaction mixture water and ethyl acetate were added. The organic layer was separated, dried, filtered and the solvent was evaporated to dryness. The yellow residue was purified by flash-chromatography (n-heptane/DCM) to give 769 mg (29 %) of the title compound as a white solid. Rt = 2.393 min (HPLC method A).

4923-87-9 5-Bromobenzothiophene 2776578, abenzothiophene compound, is more and more widely used in various.

Reference£º
Patent; MERCK PATENT GMBH; CANCER RESEARCH TECHNOLOGY LIMITED; SCHIEMANN, kai; STIEBER, Frank; BLAGG, Julian; MALLINGER, Aurelie; WAALBOER, Dennis; RINK, Christian; CRUMPLER, Simon Ross; WO2014/63778; (2014); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

Downstream synthetic route of 4923-87-9

4923-87-9 5-Bromobenzothiophene 2776578, abenzothiophene compound, is more and more widely used in various.

4923-87-9, 5-Bromobenzothiophene is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of 5-bromo-1-benzothiophene (2 g, 9.385 mmol), phenylboronic acid (1.2 g, 9.841 mmol), Pd(PPh3)4, (544 g, 0.471 mmol), potassium carbonate (1.9 g, 13.747 mmol) in toluene and water (20+20 mL) mixture was refluxed at 100C for overnight. After completion of the reaction, the mixture was cooled to room temperature, diluted with ethyl acetate, filtered through a Celite bed, and washed with ethyl acetate. The combined filtrate was washed with water and brine. The organic layer was dried over sodium sulfate and concentrate under reduced pressure to give residue which was purified by column chromatography using hexane as eluent on silica gel to afford 5-phenyl-1-benzothiophene (1.7 g, 8.084 mmol, 86%) as white solid. ?H-NMR (400 MHz, CDC13): oe 7.95 (d, J=l.5 Hz, 1H), 7.86 (dd, J?=8.5 Hz, J?0.7 Hz, 1H), 7.60-7.58 (m, 2H), 7.52 (dd, J?=8.3 Hz, J?=1.7 Hz, 1H), 7.41-7.37 (m, 3H), 7.32-7.27 (m, 2H).

4923-87-9 5-Bromobenzothiophene 2776578, abenzothiophene compound, is more and more widely used in various.

Reference£º
Patent; CURADEV PHARMA PRIVATE LTD.; BANERJEE, Monali; MIDDYA, Sandip; SHRIVASTAVA, Ritesh; RAINA, Sushil; SURYA, Arjun; YADAV, Dharmendra B.; YADAV, Veejendra K.; KAPOOR, Kamal Kishore; VENKATESAN, Aranapakam; SMITH, Roger A.; THOMPSON, Scott K.; WO2014/186035; (2014); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem