Category: 20870-78-4

Electric Literature of 20870-78-4,Some common heterocyclic compound, 20870-78-4, name is 5-Bromoindolin-2-one, molecular formula is C8H6BrNO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To 10 ml schlenk bottle by adding 5 – bromo -2 – indolone (1 a, 0.3 mmol), tert-butyl nitrite (t – BuONO, 2 a, 0.6 mmol) and THF (2 ml), then oxygen atmosphere (1 atm) next, the reactor is placed 25 C stirring under the conditions of reaction, monitoring the reaction by TLC or GC process, to the reaction raw material 5 – bromo -2 – indolone reaction is complete, to stop the reaction, the reaction the fluid uses full and salt water washing, recovering the organic phase, the aqueous phase is extracted with ethyl acetate, the combined organic phase; organic phase was dried with anhydrous sodium sulfate, filtered, distilled under reduced pressure, the residue by column chromatography (petroleum ether/ethyl acetate) separation to obtain the target product 5 – […], I – 6, the isolation yield is 76%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromoindolin-2-one, its application will become more common.

Reference:
Patent; Ningbo University; Huang Yiling; Wei Wenting; Ying Weiwei; Wu Yi; Wu Kewei; Cao Yiqi; Wang Yining; Zhu Liwei; (8 pag.)CN107141246; (2017); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 20870-78-4, These common heterocyclic compound, 20870-78-4, name is 5-Bromoindolin-2-one, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a solution of commercial available 5-bromoindoline-2-one 2b (425 mg, 2 mmol) and pyrrole 3 (636 mg, 2.4 mmol) in ethanol (4.0 mL) six drops of piperidine were added and the mixture was heated for six hours under reflux. After cooling on ice the precipitate was filtered off, washed with ethanol and dried under vacuum to give 5 (886 mg) as an orange solid in 96% yield, mp: 245-247C, HNMR (d, ppm, DMSO-d): 0.97 (t, 6H, N(CH2CH3)2); 2.43 (s, 3H, CH3); 2.44 (s, 3H, CH3); 2.50 (m, 6H, 3xCH2); 3.29 (m, 2H, NH-CH2); 6.82 (d, 1H, 7-H); 7.25 (d, 1H, 6-H); 7.42 (s, 1H, 4-H); 7.77 (s, 1H, NH-CH2); 8.10 (s, 1H, Hvinyl); 10.99 (s, 1H, NHindole); 13.62 (s, 1H, NHpyrrole); ESI-MS (ES+): m/z=461 (M+H)+

Statistics shows that 5-Bromoindolin-2-one is playing an increasingly important role. we look forward to future research findings about 20870-78-4.

Reference:
Article; Kuchar, Manuela; Oliveira, Maria Cristina; Gano, Lurdes; Santos, Isabel; Kniess, Torsten; Bioorganic and Medicinal Chemistry Letters; vol. 22; 8; (2012); p. 2850 – 2855;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 20870-78-4, These common heterocyclic compound, 20870-78-4, name is 5-Bromoindolin-2-one, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: To a Schlenk tube were added oxindole 1 (0.3 mmol), t-BuONO (0.6 mmol), andTHF (2 mL). Then the tube was stirred at 50 C under 1 atm of O2 for the indicatedtime until complete consumption of starting material monitored by TLC analysis.After the reaction was finished, the reaction mixture was washed with brine. The aqueous phase was re-extracted with ethyl acetate. The combined organic extractswere dried over Na2SO4, removal of the solvent under vacuum afforded the crudeproduct, which was purified further by column chromatography using hexane-ethylacetate.

Statistics shows that 5-Bromoindolin-2-one is playing an increasingly important role. we look forward to future research findings about 20870-78-4.

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 20870-78-4, name is 5-Bromoindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., name: 5-Bromoindolin-2-one

4 mmol of 5-bromo-2-fluorenone (IX) was dissolved in 20 ml of tetrahydrofuran solution, 4.8 mmol of sodium hydrogencarbonate was added, and then 8 mmol of di-tert-butyl dicarbonate was added, and the reaction system was stirred at 66 C. The reaction was quenched by TLC until the material disappeared, and then the mixture was evaporated to ethyl ether.Hexane:Separation and purification of ethyl acetate = 5:1 as eluent gave 670 mg of white solid. The yield was 54%.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 20870-78-4.

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 20870-78-4, name is 5-Bromoindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 20870-78-4

5-Bromo-1,3-dihydro-indol-2-one (Aldrich, 1.06 g, 5 mmol) was coupled with bis(pinacolato)diboron (Aldrich, 1.52 g, 6 mmol) catalyzed by PdCl2(dppf)2.CH2Cl2 (Aldrich, 82 mg, 0.1 mmol) using KOAc (Aldrich, 0.98 g, 10 mmol) as base in dioxane (anhydrous, Aldrich, 50 mL) at 80 C. for 10 h. After being cooled down to ambient temperature, the mixture was diluted with EtOAc (50 mL) and washed with brine (2×10 mL). The organic solution was then concentrated under vacuum. The title compound was purified by chromatography (SiO2, hexane:EtOAc, 70:30, Rf. 0.5) as a solid (0.96 g, yield, 74%). 1H NMR (300 MHz, CDCl3) delta 1.24 (s, 3 H), 1.28 (s, 3 H), 1.34 (s, 6 H), 3.69 (s, 2 H), 6.86 (d, J=7.8 Hz, 1 H), 7.57-7.78 (m, 2H) ppm. MS (DCl/NH3): 260 (M+H)+.

According to the analysis of related databases, 20870-78-4, the application of this compound in the production field has become more and more popular.

Application of 20870-78-4, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 20870-78-4 name is 5-Bromoindolin-2-one, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

5-Bromo-2-oxindole 16 (150 mg, 0.71 mmol), benzeneboronic acid (113 mg, 0.92 mmol), tetrakis(triphenylphosphine)palladium(0) (61 mg, 0.05 mmol) and Natrium carbonate (250 mg, 2.41 mmol) were suspended in toluene (1.5 mL) and ethanol (1.5 mL) and refluxed for 12 h at 100 C. Water was added and extracted 3 times with ethyl acetate. The combined organic layers were wash with 1N hydrochloric acid, brine, dried over MgSO4, filtered and concentrated in vacuum to give 75 mg (51%) as a light brown solid and was used for the next step without further structure determination.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromoindolin-2-one, and friends who are interested can also refer to it.

Reference:
Article; Goering, Stefan; Taymans, Jean-Marc; Baekelandt, Veerle; Schmidt, Boris; Bioorganic and Medicinal Chemistry Letters; vol. 24; 19; (2014); p. 4630 – 4637;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 20870-78-4,Some common heterocyclic compound, 20870-78-4, name is 5-Bromoindolin-2-one, molecular formula is C8H6BrNO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Example 51 5-(5-Bromo-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic Acid (2-diethylamino-ethyl)amide 5-Bromo-1,3-dihydroindol-2-one (0.17 g, 0.8 mmol) was condensed with 5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (2-diethylaminoethyl)amide (0.2 g) to give 0.09 g (26%) of the title compound as a yellow solid. 1H-NMR (360 MHz, DMSO-d6) delta 13.61 (s, br, 1H, NH), 10.98 (, br, 1H, NH), 8.09 (d, J=1.7 Hz, 1H, H-4), 7.76 (s, 1H, H-vinyl), 7.42 (t, J=5.5 Hz, 1H, CONHCH2), 7.24 (dd, J=1.7 & 8.0 Hz, 1H, H-6), 6.82 (d, J=8.0 Hz, 1H, H-7), 3.23-3.32 (m, 2H, NCH2), 2.46-2.55 (m, 6H, 3*NCH2), 2.43 (s, 3H, CH3), 2.42 (s, 3H, CH3), 0.96 (t, J=7.2 Hz, 6H, 2*NCH2CH3). MS-EI m/z 458 and 460 [M+-1 and M++1].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromoindolin-2-one, its application will become more common.

Reference:
Patent; Pharmacia Corporation; US2003/216410; (2003); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 20870-78-4,Some common heterocyclic compound, 20870-78-4, name is 5-Bromoindolin-2-one, molecular formula is C8H6BrNO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

5-Bromo-2-oxindole (10 g, 47 mmol), 7.4 g (61 mmol) of benzeneboronic acid, 4.0 g (3.5 mmol) of tetrakis(triphenylphosphine)palladium(0), 17 g (160 mmol) of anhydrous sodium carbonate, 100 mL of toluene and 100 mL of ethanol were refluxed for 18 hours. The mixture was vacuum filtered hot to remove insolubles. The organic layer of the filtrate was separated while hot and concentrated. The solids were collected by vacuum filtration and washed with 5 mL of ethanol. The solids were triturated with 1 N hydrochloric acid, collected by vacuum filtration, washed with water and dried under vacuum. The crude solids were triturated with dichloromethane and dried under vacuum to give 8.3 g (63% yield) of the title compound. 1H-NMR (dimethylsulfoxide-d6) delta10.00 (s, 1H), 7.20-6.80 (multiplets, 9H), 3.50 (s, 3H).

The synthetic route of 20870-78-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUGEN, Inc.; US2004/186160; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 20870-78-4, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 20870-78-4, name is 5-Bromoindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

5-(4,4,5,5-Tetramethyl-l,3,2-dioxaboroIan-2-yl)-l,3-dihydroindol-2-one; A mixture of 5-bromo-2,3-dihydroindol-2-one (500 mg), bis(pinacolato)diboron (899 mg) and potassium acetate (695 mg) in DMF (20 mL) was degassed for 5 minutes. 1,1′- 5 Bis(diphenylphosphino)ferrocenedichloropalladium(II) dichloromethane adduct (78 mg) was added to the mixture and the reaction was heated to 8O0C and left to stir for 3 hours. The reaction mixture was filtered through celite and concentrated in vacuo. The residue was suspended in water (50 mL) and extracted with ethyl acetate (2 x 50 mL). The organics were dried (MgSO4), filtered and concentrated in vacuo to give the desired 0 material as a brown solid. (611 mg). Mass Spectrum; M+H+MeCN+ 301.NMR Spectrum: 1H NMR (DMSOd6) deltal.28 (12H, s), 3.47 (2H, s), 6.82 – 6.84 (IH, d), 7.51 (2H, m), 10.52 (IH, s)

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 5-Bromoindolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/80382; (2007); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 20870-78-4, name is 5-Bromoindolin-2-one, A new synthetic method of this compound is introduced below., Quality Control of 5-Bromoindolin-2-one

To a solution of 5-Bromo-1,3-dihydro-indol-2-one (318 mg, 1.5 mmol) and Bis(pinacolato)diboron (420 mg, 1,65 mmol) in dioxane (15 mL) was added KOAc (516 mg, 5.25 mmol). The resulting mixture was degassed, treated with [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium methylene choloride complex (62 mg, 0.075 mmol), heated at 90 C. for 12 h and concentrated. The residue was dissolved in CH2Cl2 (100 mL), washed with water (100 mL) and brine (100 mL), dried (MgSO4), filtered and concentrated. The concentrate was purified by flash chromatography on silica gel eluding with 30% ethyl acetate/hexanes to afford 320 mg of Example 133a (82%). 1H NMR (300 MHz, DMSO-D6) delta ppm 1.27 (s, 12H) 3.46 (s, 2H) 6.81 (d, J=7.72 Hz, 1H) 7.49 (m, 2H) 10.51 (s, 1H)) MS (ESI) m/z 260.2 (M+H)+, 276.8 (M+NH4)+

The synthetic route of 20870-78-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Iyengar, Rajesh R.; Judd, Andrew S.; Zhao, Gang; Kym, Philip R.; Sham, Hing L.; Gu, Yugui; Liu, Gang; Liu, Mei; Zhao, Hongyu; Clark, Richard F.; Frevert, Ernst U.; Cool, Barbara L.; Zhang, Tianyuan; Keyes, Robert F.; Hansen, Todd M.; Xin, Zhili; US2005/38068; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem