Category: indolines-derivatives

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 3335-98-6 as follows. Recommanded Product: 3335-98-6

General procedure: A mixture of isatins (1, 1.0 mmol), indolin-2-ones (2, 1.0 mmol) and ZrCl4 (23 mg, 0.1 mmol) was heated in anhydrous ethanol (5 mL) under reflux. After the disappearance of the reactants (8-12 h, monitored by TLC), the mixture was slowly cooled to room temperature. The red solids precipitated and were collected by filtration, then washed by a small amount of anhydrous ethanol to deliver pure compounds 3.

According to the analysis of related databases, 3335-98-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Liu, Meilin; Qiu, Shaozhong; Ye, Yu; Yin, Guodong; Tetrahedron Letters; vol. 57; 52; (2016); p. 5856 – 5858;,
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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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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. 84575-27-9, name is 7-Methoxyindoline-2,3-dione, A new synthetic method of this compound is introduced below., Product Details of 84575-27-9

To a stirring suspension of 7-methoxyindoline-2,3-dione (11 g, 64 mmol) in water (64 ml) was added potassium hydroxide (5.5 g, 80 mmol). The reaction mixture was stirred at 40C for 5h. The reaction mixure was allowed to cool to room temperature, the precipitate was removed through filtration and the filtrate lyophilized to give the title compound as a white solid. The product was used without purification in the next step. LC/MS = 196 [M+1].

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ALI, Amjad; ZHOU, Gang; KUANG, Rongze; LIM, Yeon-Hee; LO, Michael Man-Chu; TING, Pauline, C.; BIJU, Purakkattle; RUIZ, Manuel de Lera; DEGRADO, Sylvia, J.; TUNG, Alexander, L.; HENDERSON, Timothy, J.; HONG, Liwu; KIM, Jae-Hun; KIM, David Won-Shik; LEE, Joe, F.; WU, Jie; WU, Heping; XIAO, Yushi; YU, Tao; ZHU, Xiaohong; MCCORMICK, Kevin, D.; TAGAT, Jayaram, R.; XIAO, Dong; KHAN, Tanweer; CAO, Jianhua; BERLIN, Michael; ZHANG, Yonglian; (80 pag.)WO2016/126570; (2016); A1;,
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Application of 2058-72-2, 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. 2058-72-2 name is 5-Bromo-1-methylindoline-2,3-dione, 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.

General procedure: A solution of isatins 1 (0.6 mmol), 3-methyl-4-nitro-5-isatylidenylisoxazoles 2 (0.4 mmol) and proline or thioproline (0.8 mmol) in the 10.0 mL of EtOH at reflux for 5 h. After completion of the reaction, as indicated by TLC, the reaction mixture was directly subjected to flash column chromatography on silica gel (petroleum ether/EtOAc = 5:1-3:1) to furnish the corresponding products 3.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-1-methylindoline-2,3-dione, and friends who are interested can also refer to it.

Reference:
Article; Lin, Bing; Zhang, Wen-Hui; Wang, Dan-Dan; Gong, Yi; Wei, Qi-Di; Liu, Xiong-Li; Feng, Ting-Ting; Zhou, Ying; Yuan, Wei-Cheng; Tetrahedron; vol. 73; 34; (2017); p. 5176 – 5188;,
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Adding a certain compound to certain chemical reactions, such as: 39603-24-2, name is 5,7-Dimethylindoline-2,3-dione, 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 39603-24-2, Computed Properties of C10H9NO2

General procedure: To a round bottom flask containing 5 ml glycerol was added respective isatin (1 mmol) and respective thiosemicarbazide/semicarbazide (1 mmol) under stirring. The temperature of the reaction was set at 40 oC and the resulting mixture was stirred till completion and progress of reaction was monitored with TLC (Hexane/EtOAc 2:1). The reaction was quenched with hot water whence glycerol got dissolved in water and the resulting insoluble solid precipitate was filtered and dried to obtain the crude product which was as good as pure (1H NMR). The aqueous phase containing glycerol was extracted with methyl t-butyl ether (4 ¡Á 25 mL) to remove any trace of organic compounds and then evaporated in vacuo to give pure glycerol which was used for the next cycle.

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, 5,7-Dimethylindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Tiwari, Jyoti; Saquib, Mohammad; Singh, Swastika; Tufail, Fatima; Singh, Jaya; Singh, Jagdamba; Synthetic Communications; vol. 47; 21; (2017); p. 1999 – 2006;,
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13220-46-7, name is 4-Methylindolin-2-one, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. SDS of cas: 13220-46-7

5-Bromo-4-methyloxindole and 5,7-Dibromo-4-methyloxindole 4-Methyl-2-oxindole (5 g) in 40 mL of acetonitrile was treated with 7.26 g of N-bromosuccinimide and stirred at room temperature for 4 hours. Thin layer chromatography (ethyl acetate:hexane 1:2, silica gel) showed a mixture of 5-bromo (Rf 0.3) and 5,7-dibromo (Rf 0.5) products. Another 7.26 g of N-bromosuccinimide was added and the mixture stirred for 4 additional hours. The solid was collected by vacuum filtration, washed with 20 mL of acetonitrile and dried to give a 1:1 mixture of mono and dibromo compounds. The filtrate was concentrated and chromatographed on silica gel (ethyl acetate:hexane (1:2)) to give 1.67 g of 5-bromo-4-methyl-2-oxindole as a beige solid. The remaining 1:1 mixture of solids was recrystallized twice from glacial acetic acid to give 3.2 g of 5,7-dibromo-4-methyl-2-oxindole as a light orange solid. The filtrates from this material were chromatographed as above to give 0.6 g of 5-bromo-4-methyl-2-oxindole and 0.5 g of 5,7-dibromo-4-methyl-2-oxindole.

The synthetic route of 13220-46-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUGEN, Inc.; US2003/69421; (2003); A1;; ; Patent; Sugen, Inc.; US6051593; (2000); A;,
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Synthetic Route of 20876-36-2, 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. 20876-36-2, name is 5-Aminoindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows.

Part 1: tert-Butyl 2-oxo-2,3-dihydro-1H-indol-5-ylcarbamate (21): To a mixture of 5-amino-1,3-dihydro-2H-indol-2-one (148 mg, 11.0 mmol), di-tert-butyl dicarbonate (262 mg, 1.2 mmol), and Et3N (279 muL, 2.0 mmol) was added dry THF (5 mL). The suspension was then stirred at rt for 24 h. The reaction was concentrated in vacuo to yield tert-butyl 2-oxo-2,3-dihydro-1H-indol-5-ylcarbamate as a brown solid. 1H NMR (CDCl3, 400 MHz): delta 1.52 (s, 9H), 3.52 (s, 2H), 6.38 (brs, 1H), 6.76 (d, J=8.0 Hz, 1H), 7.07 (dd, J=2.4, 8.4 Hz, 1H), 7.26 (d, J=2.4 Hz, 1H), 7.42 (brs, 1H). MS (ES+): m/z 249 [M+1].

The chemical industry reduces the impact on the environment during synthesis 5-Aminoindolin-2-one. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Li, An-Hu; Dong, Hanqing; Zhang, Tao; US2006/63791; (2006); A1;,
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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 20780-77-2 as follows. Computed Properties of C8H4INO2

General procedure: A mixture of isatin 1 (1.0 mmol), malononitrile or cyanoacetic ester 2 (1.0 mmol), phthalhydrazide (1.0 mmol), and NiCl2 (0.2 mmol) in PEG 600 (5 mL) was stirred at 100 C for the appropriate time (refPreviewPlaceHolderTable 2). After complete conversion as indicated by TLC, water was added and the product was extracted with ethyl acetate (2¡Á10 ml). The organic phase was dried over anhydrous Na2SO4, and concentrated under reduced pressure. The crude product was recrystallized from ethanol to afford the pure product.

According to the analysis of related databases, 20780-77-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhang, Xiao-Nan; Li, Yong-Xiao; Zhang, Zhan-Hui; Tetrahedron; vol. 67; 38; (2011); p. 7426 – 7430;,
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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 20870-90-0 as follows. HPLC of Formula: C9H8BrNO

A mixture of 5-bromo-1-methyl-2-oxoindoline (500 mg, 2.212 mmol), Bis(pinacolato)diboron (730 mg, 2.88 mmol), KOAc (651 mg, 6.64 mmol) and PdCl2(dppf).CH2CI2 complex (81 mg, 0.1 1 1 mmol) in Dioxane (8.32 mL) was stirred at 1 15C for 20 min. The reaction mixture was cooled down to RT, filtered through a pad of Celite and the filtrate was concentrated under reduced pressure. EtOAc and saturated aqueous NaHC03 solution were added and both phases were separated. The organic phase was washed twice with brine, dried over MgS04, filtered and concentrated under reduced pressure to afford the title product (1.04 g, 2.208 mmol, quantitative yield) as brown solid. Rt = 1.917 min (LC-MS); ESI-MS = 274.1 [M+1]+ (LC-MS).

According to the analysis of related databases, 20870-90-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; ARISTA, Luca; CHAMOIN, Sylvie; D’ALESSANDRO, Pier Luca; LINDVALL, Mika; LIZOS, Dimitrios; STIEFL, Nikolaus Johannes; TEIXEIRA-FOUCHARD, Sylvie; ULLRICH, Thomas; WEILER, Sven; (151 pag.)WO2019/102256; (2019); A1;,
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Application of 39755-95-8, 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 39755-95-8 as follows.

Synthesis of 5-methoxyoxindole; [0095] To a solution of 5-methoxyisatin ( 10.62 g, 60 mmol) in DMSO (30 mL) was added N2H4 xH20 (hydrazine hydrate, 6 mL, 120 mmol) dropwise over 5 min (exothermic). After addition, the resulting mixture was heated at 140 C (oil temp.) for 2h and then cooled to rt. After diluting with H20 (30 mL), 6 M HC1 (12 mL, 72 mmol) was added and the resulting mixture was stirred for lh at rt. Ice (30 mL) was added and the reaction mixture was stirred O/N at rt. The precipitate formed was collected by suction filtration, rinsed with H20, then dried to give the 5-methoxyoxindole (6.523 g) as a brown solid, (about 10% impurity being the oxime from starting material 5-methoxyisatin) NMR (400 MHz, d6- DMSO) 6.78 (s, 1H), 6.85 (s, 1 H), 6.72-6.79 (m, 2H), 3.39 (s, 3H); ESI 164.0 [M + H]+, calcd for [C9H9N02 + H]+ 164.1.

According to the analysis of related databases, 39755-95-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UNIVERSITY HEALTH NETWORK; SAMPSON, Peter Brent; LIU, Yong; LI, Sze-Wan; FORREST, Bryan T.; PAULS, Heinz W.; EDWARDS, Louise G.; FEHER, Miklos; PATEL, Narendra Kumar B.; LAUFER, Radoslaw; PAN, Guohua; WO2011/123946; (2011); A1;,
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