Category: 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. Recommanded Product: 20870-78-4

5-Phenyloxindole 5-Bromo-2-oxindole (5 g, 23.5 mmol) was dissolved in 110 mL toluene and 110 mL ethanol with stirring and a little heat. Tetrakis(triphenylphosphine)palladium(0) (1.9 g, 1.6 mmol) was added followed by 40 mL (80 mmol) 2M aqueous sodium carbonate. To this mixture was added benzene boronic acid (3.7 g, 30.6 mmol) and the mixture was heated in a 100 C. oil bath for 12 hours. The reaction was cooled, diluted with ethyl acetate (500 mL), washed with saturated sodium bicarbonate (200 mL), water (200 mL), 1N HCl (200 mL) and brine (200 mL). The organic layer was dried over magnesium sulfate and concentrated to afford a brown solid. Trituration with dichloromethane afforded 3.8 g (77%) of 5-phenyl-2-oxindole as a tan solid. 1H NMR (360 MHz, DMSO-d6) delta 10.4 (br s, 1H, NH), 7.57 (dd, J=1.8 and 7.2 Hz, 1H), 7.5 to 7.35 (m, 5H), 7.29 (m, 1H), 6.89 (d, J=8.2 Hz, 1H), 3.51 (s, 2H, CH2CO). MS m/z 209 [M+].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 20870-78-4, its application will become more common.

Reference:
Patent; Sugen, Inc.; US6878733; (2005); B1;,
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In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 20870-78-4 as follows. Application In Synthesis of 5-Bromoindolin-2-one

A mixture of 28b (513mg, 2.42mmol), 4,4,5,5-tetramethyl-2-(4,4,5,5- tetramethyl (l,3,2-dioxaborolan-2-yl))-l ,3,2-dioxaborolane (716mg, 2.82mmol) and KOAc (878mg, 8.95mmol) in dioxane (2OmL) was purged with nitrogen for lOmin, then added Pd(dppf)Cl2. CH2Cl2 (108mg, 0.13mmol). The resulting mixture was stirred at 800C overnight and evaporated. The residue was dissolved in ethyl acetate and filtrated. The filtrate was washed with brine (15mLchi2), dried over Na2SO4 and concentrated. The residue was purified by column chromatography (EA: PE =4:1) to afford 28c (470mg, 75%).

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.

Reference:
Patent; XCOVERY, INC.; WO2008/88881; (2008); A1;,
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Related Products of 20870-78-4, The chemical industry reduces the impact on the environment during synthesis 20870-78-4, name is 5-Bromoindolin-2-one, I believe this compound will play a more active role in future production and life.

Reference Example 27 Production of (Z)-5-((5-bromo-2-oxoindolin-3-ylidene)methyl)-N-(2-(diethylamino)ethyl)-2,4-dimethyl-1H-pyrrole-3-carboxamide To the solution of 5-bromoindolin-2-one (262 mg, 1.24 mmol) in EtOH (5 ml) was added N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide (298 mg, 1.12 mmol) and piperidine (112 muL, 1.13 mmol). The mixture was stirred at 80 C. for 1 hour. After cooled down to room temperature, the reaction mixture was concentrated, filtrated, and washed with EtOH to give (Z)-5-((5-bromo-2-oxoindolin-3-ylidene)methyl)-N-(2-(diethylamino)ethyl)-2,4-dimethyl-1H-pyrrole-3-carboxamide (368 mg) as orange solid. MS m/z 459.4/461.4 (M+H)

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; Tsuboi, Katsunori; Takanashi, Yosuke; Tojo, Shingo; Kodama, Tomohiro; Kubota, Katsumi; Kanai, Toshio; US2014/275076; (2014); A1;,
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Reference 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-bromoindolin-2-one (1.50 g; 6.93 mmol; 1.00 eq) was dissolved in THF (45.00 ml) then di-ferf-butyl dicarbonate (2.29 g; 10.40 mmol; 1.50 eq) and NaHC03 (5.24 g; 62.41 mmol; 9.00 eq) were added. The mixture was stirred 3h under reflux. Solids were filtered and the filtrate was concentrated. The residue was purified by chromatography (gradient from 100% n-heptane to 80/20 n-heptane / EtOAc) to give tert-butyl 5-bromo-2-oxo-indoline-1-carboxylate (1.52 g; 71 %) as a white solid.

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; Eng Bang Tiba; Ba Seu-ma-tin; Kon Tal-sil-bi-e; Ju Ni-en-jang—ru-i-seu; Ma Sa-reu-di-e-reu-keu-ri-seu-tin; Mon Tal-be-ti-keu-ri-seu-chan; Su Deu-an-ne; (111 pag.)KR2019/137803; (2019); A;,
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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.

NaH (60 % in mineral oil; 5.66 g, 141.48 mmol) was added portionwise to a mixture of 5-bromo-l,3-dihydro-2H-Indol-2-one (10.0 g, 47.16 mmol) in THF (100 ml) at 0 C.The mixture was stirred for 30 min, and then CH3I (21.42 g, 150.91 mmol) was added.The r.m. was stirred at 0 C for 30 min. Subsequently, H20 (2 ml) was added dropwise.The solvent was removed in vacuo. The residue was dissolved in H20 (q.s.) and extracted with EtOAc. The separated organic layer was washed with brine, dried (Na2S04), filtered and evaporated in vacuo. The residue was purified by column chromatography (eluent: PE/EtOAc 20/1). The desired fractions were collected and the solvent was evaporated. Yield: 9.5 g of intermediate 3 (79 % yield).

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.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; MEERPOEL, Lieven; MAES, Louis, Jules, Roger, Marie; DE WIT, Kelly; WO2012/84804; (2012); A1;,
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Adding some certain compound to certain chemical reactions, such as: 20870-78-4, name is 5-Bromoindolin-2-one, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 20870-78-4. 20870-78-4

Description 3:(Z)-3-{(1H-Pyrrol-2-yl)methylene)-5-bromoindolin-2-oneIn a 35 ml microwave tube were placed 5-bromo-1,3-dihydro-2H-indol-2-one (1 mmol), pyrrole-2-carbaldehyde (1.2 mmol), piperidine (2 drops), ethanol (10 ml) and a magnetic stir bar. The vessel was sealed with a septum and placed in the microwave cavity. Initial microwave irradiation of 200 W was used, the temperature being ramped from RT to 150 C. Once 150 C was reached the reaction vessel was held at this temperature for 30 min by moderation of the initial microwave power. After cooling, solvent was removed in vacuo and ethyl acetate was added to the reaction mixture. The precipitate was collected by filtration and washed with ethyl acetate (2x 10 ml) to afford a yellow-brown solid. The results set out below identify the product as the title compound D3.

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 5-Bromoindolin-2-one.

Reference:
Patent; University of Greenwich; SPENCER, John; WO2012/25726; (2012); A1;,
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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. 20870-78-4

To a stirred solution of 5-bromoindolin-2-one (LIV, 7.25 g, 34.36 mmol) in tetrahydrofuran (70 mL) under nitrogen atmosphere, was added sodium hydride (5.9 g, 137.0 mmol) portion-wise at 0 C. After addition of sodium hydride, the reaction was stirred at room temperature for 30 min, then cooledto 0 C. methyl iodide (8.5 mL, 137.0 mmol) was added, and then allowed to stir at room temperature for 2h. The reaction mass was cooled to 0 C and carefully quenched with ice-water. Then the reaction mixture was diluted with water (150 mL) and ethylacetate (150 mL). The organic layer was separated, washed with water, brine solution, dried over sodium sulphate and concentrated under reduced pressure to afford the titled product as brown colour solid (LV, 7.4 g, 85%). LC-MS m/z calcd for CnHi2BrNO, 253.0; found 254.0 [M+H]+.

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

Reference:
Patent; JUBILANT BIOSYS LIMITED; RAJAGOPAL, Sridharan; HALLUR, Mahanandeesha S.; DEWANG, Purushottam; MURUGAN, Kannan; KUMAR C.H., Durga Prasanna; IYER, Pravin; MULAKALA, Chandrika; SIVANANDHAN, Dhanalakshmi; NAIR, Sreekala; ZAINUDDIN, Mohd.; TANTRY, Subramanyam Janardhan; GAJENDRAN, Chandru; RAJAGOPAL, Sriram; (334 pag.)WO2017/195216; (2017); A1;,
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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.

Under argon, 2.64 g (66 mmol) of sodium hydride (60% in mineral oil) were suspended in 25 ml of THF and cooled to 0 C. A solution of 4.00 g (18.86 mmol) of 5-bromo-1,3-dihydro-2H-indol-2-one in 25 ml of DMF was added dropwise and the mixture was stirred at 0 C. for 30 min. Subsequently, 4.11 ml (66 mmol) of methyl iodide were slowly added dropwise thereto, then the reaction mixture was warmed to RT and stirring continued at this temperature overnight. For workup, the mixture was poured onto 200 ml of 1M hydrochloric acid and extracted three times with ethyl acetate. The combined organic phases were washed with water, then a saturated sodium chloride solution, dried over sodium sulphate and concentrated on a rotary evaporator. The residue was dissolved in 200 ml of acetonitrile and the mineral oil was extracted with n-pentane. The acetonitrile phase removed was concentrated on a rotary evaporator and the remaining brownish solid was dried under HV. This gave 4.45 g (84% of theory) of the title compound in 91% purity. LC-MS (Method 3): Rt=1.18 min; m/z=254, 256 (M+H)+. 1H NMR (400 MHz, DMSO-d6): delta [ppm]=1.27 (s, 6H), 3.12 (s, 3H), 6.99 (d, 1H), 7.45 (dd, 1H), 7.60 (d, 1H).

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; BAYER PHARMA AKTIENGESELLSCHAFT; Fuerstner, Chantal; Ackerstaff, Jens; Straub, Alexander; Meier, Heinrich; Tinel, Hanna; Zimmermann, Katja; Tersteegen, Adrian; Zubov, Dmitry; Kast, Raimund; Schamberger, Jens; Schaefer, Martina; Boerngen, Kirsten; US2015/148340; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 20870-78-4, name is 5-Bromoindolin-2-one, belongs to indolines-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 20870-78-4, 20870-78-4

A. 5-(4,4,5,5-Tetramethyl-l ,3>2-dioxaborolan-2-yl)indolin-2-one. Bis(pinacolato)diboron (1.31 g, 4.71 mmol), dichloro[l,l’-bis(diphenylphosphino) ferrocenejpalladium (II) dichloro-methane (385 mg, 0.47 mmol) and potassium acetate (1.38 g, 14.1 mmol) were successively added to a solution of 5-bromooxindole (1.0 g, 4.71 mmol) in methylene chloride (25 mL), followed by DMSO (15 mL). The crude mixture was diluted with water, extracted with methylene chloride (3x). the combined organic fractions were washed with water, brine, dried over magnesium sulfate, filtered, and the volatiles were removed under reduced pressure. The crude product was triturated with diethyl ether, sonicated, and the precipitate was collected by filtration to afford the title compound (165 mg, 14%). MS (ESI) m/z 260.3 [M+l]+.

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; SIGNAL PHARMACEUTICALS, LLC; WO2008/51493; (2008); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

A common compound: 20870-78-4, name is 5-Bromoindolin-2-one, belongs to indolines-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 20870-78-4

General procedure: To a Schlenk tube were added indolin-2-one 1 (0.3 mmol), t-BuOOH (0.6 mmol), and DCE (2 mL). Then the tube was stirred at 85 oC under air for the indicated time 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 (3¡Á10 mL). The combined organic extracts were dried over Na2SO4, removal of the solvent under vacuum afforded the crude product, which was purified further by column chromatography using hexane-ethyl acetate (10:1).

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, 20870-78-4, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Ying, Wei-Wei; Zhu, Wen-Ming; Liang, Hongze; Wei, Wen-Ting; Synlett; vol. 29; 2; (2018); p. 215 – 218;,
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