Category: 324-03-8

324-03-8, Name is 6-Fluoroindoline-2,3-dione, 324-03-8, 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.

General procedure: Isatin derivatives (S1) were synthesized by treating isatins with NaH and then reacting with methyl iodide or benzyl bromide or allyl bromide, respectively, in dry DMF at room temperature.

Statistics shows that 6-Fluoroindoline-2,3-dione is playing an increasingly important role. we look forward to future research findings about 324-03-8.

Reference:
Article; Zhang, Lin-Lin; Da, Bing-Chao; Xiang, Shao-Hua; Zhu, Shuai; Yuan, Zi-Yun; Guo, Zhen; Tan, Bin; Tetrahedron; vol. 75; 12; (2019); p. 1689 – 1696;,
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324-03-8, Adding some certain compound to certain chemical reactions, such as: 324-03-8, name is 6-Fluoroindoline-2,3-dione, 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 324-03-8.

Example 125 3-Cyclopentyl-2-(6-fluoro-2-oxo-2,3-dihydro-indol-1-yl)-N-thiazol-2-yl-propionamide A stirred suspension of sodium hydride (60% dispersion in oil, 290 mg) in N,N-dimethylformamide at 0 C. was treated with a solution of 6-fluoro-1H-indole-2,3-dione (1.0 g) in N,N-dimethylformamide (total volume, 20 mL). The reaction mixture was stirred for 30 min at 0 C. and then 2-bromo-3-cyclopentyl-propionic acid methyl ester (prepared as in Example 1, 1.71 g) was added and it was stirred for 1 h at 0 C. It was then slowly allowed to warm to room temperature and stirred for another 3 h at room temperature. After this time, the reaction mixture was diluted with water and extracted with methylene chloride (3*10 mL). The organic layers were combined and dried over sodium sulfate, filtered and the filterate concentrated in vacuo. The crude material was purified by column chromatography (silica gel, 5% ethyl acetate/hexanes) to afford 3-cyclopentyl-2-(6-fluoro-2,3-dioxo-2,3-dihydro-indol-1-yl)-propionic acid methyl ester (1.0 g, 52%).

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 324-03-8.

Reference:
Patent; Kester, Robert Francis; US2012/142705; (2012); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 324-03-8, name is 6-Fluoroindoline-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 324-03-8, 324-03-8

General procedure: Compound 2h was prepared from 6-fluoro-1H-indole-2,3-dione 1f and dl-leucine in a similar manner to that described for the synthesis of compound 2a and obtained in 64% yield as a yellow solid. 1H NMR (400 MHz, DMSO-d6) delta 0.86-0.91 (m, 6H), 1.31-1.45 (m, 2H), 1.61-1.69 (m, 1H), 1.79-1.89 (m, 1H), 2.16-2.23 (m, 1H), 2.93-2.96 (m, 1H), 3.12 (s, 3H), 3.28-3.32 (m, 1H), 3.42-3.53 (m, 1H), 6.55-6.61 (m, 1H), 6.66-6.74 (m, 1H), 7.01-7.09 (m, 1H), 10.45 (s, 1H). MS m/z 321 (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, 6-Fluoroindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article in Press; Ito, Masahiro; Iwatani, Misa; Yamamoto, Takeshi; Tanaka, Toshio; Kawamoto, Tomohiro; Morishita, Daisuke; Nakanishi, Atsushi; Maezaki, Hironobu; Bioorganic and Medicinal Chemistry; (2017);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

324-03-8, 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. 324-03-8, name is 6-Fluoroindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: 5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)indolin-2-one (10 g, 38.6 mmol) was added in toluene (250 ml_). The mixture was cooled down to 0C and NaH 60% in mineral oil (2.315 g, 57.9 mmol) was added portionwise. The reaction mixture was allowed to warm up and stir at RT for 30 min. Dimethyl sulfate (5.53 ml_, 57.9 mmol) was added and the reaction mixture was heated up and stirred at 60C for 3 hr, cooled down to 5C and quenched with water (50 ml_). The reaction mixture was diluted with EtOAc and washed with saturated aqueous NaHC03 solution and brine. The organic layer was dried over MgS04, filtered and concentrated under reduced pressure to afford the title product (1 1.3 g, 36.0 mmol, 93% yield) as brown solid. Rt = 1.03 min (UPLC-MS); ESI-MS = 274.2 [M+1]+ (UPLC-MS); 1H NMR (400 MHz, DMSO-d6) d ppm 1.29 (s, 12 H) 3.13 (s, 3 H) 3.55 (s, 2 H) 6.99 (d, J= 7.82 Hz, 1 H) 7.53 (s, 1 H) 7.61 (d, J= 7.95 Hz, 1 H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

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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Indoline | C8H9N – PubChem

324-03-8,Some common heterocyclic compound, 324-03-8, name is 6-Fluoroindoline-2,3-dione, molecular formula is C8H4FNO2, 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.

In a RB flask charge under stirring at 2530 C, 336 gr of crude compound of formula lila (0,0203 mole) and dissolve in 336 mL tetrahydrofuran. To the clear solution add 1.902 gr cyanoacetic acid (0.0224 mole) and 2.7 mL triethylamine (0.0194 mole). Warm up reaction mass to reflux and continue stirring overnight.When reaction is completed, allow reaction mass to cool down (2530 C). Concentrate solvent till total dryness. To the oily residue add 168 mL D.M. water and extract three times with 336 mL ethyl acetate (each time). Combine organic layers, dry over sodium sulfate, filter and evaporate solvent till total dryness, to provide 4.116 gr of crude compound of formula ha,IH NMR (300 MHz, DMSOd6) 7,47 (dd, J1 = 82 Hz, J2 = 56 Hz, 1H), 689 682(m, 1H), 67 (dd, Ji = 9,2 Hz, J2 = 24 Hz, 1H), 664 (s, 1H), 336 (s, IH), 309 294(m, 2H). 13C NMR (75 MHz, DMSOd6) 177,4, 1636, 1439, 1438, 126,2, 1 17A, 1085, 987, 720, 26,4.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 324-03-8, its application will become more common.

Reference:
Patent; PHARMATHEN S.A.; KOFTIS, V. Theocharis; NEOKOSMIDIS, Efstratios; RAPTIS, Christos; TRAKOSSAS, Sakellarios; ANDREOU, Thanos; VARVOGLI, Anastasia – Aikaterini; (30 pag.)WO2017/67670; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

The chemical industry reduces the impact on the environment during synthesis 324-03-8, name is 6-Fluoroindoline-2,3-dione, I believe this compound will play a more active role in future production and life. 324-03-8

General Procedure: To a solution of 4-chloro isatin (500 mg, 2.75 mmol) in acetone (5 mL) was added diethylamine (314 muL, 3.02 mmol) at room temperature. The mixture was heated to 50 oC for 14 hours with magnetic stirring and then concentrated under reduced pressure. The resulting alcohol intermediate was triturated in diethyl ether with sonication, filtered and the resulting white solids were used without further purification. To a solution of the alcohol intermediate dissolved in ethanol (3 mL) was added concentrated hydrochloric acid (1 mL). The mixture was stirred at room temperature for 14 hours and then quenched with a solution of saturated sodium bicarbonate (5 mL). The mixture was extracted with dichloromethane (20 mL), concentrated and purified by silica gel flash chromatography using a gradient of 30 – 80% ethyl acetate in hexanes to afford the target compound 10 as a yellow solid.

The chemical industry reduces the impact on the environment during synthesis 324-03-8. I believe this compound will play a more active role in future production and life.

Reference:
Conference Paper; Kloeck, Cornelius; Jin, Xi; Choi, Kihang; Khosla, Chaitan; Madrid, Peter B.; Spencer, Andrew; Raimundo, Brian C.; Boardman, Paul; Lanza, Guido; Griffin, John H.; Bioorganic and Medicinal Chemistry Letters; vol. 21; 9; (2011); p. 2692 – 2696;,
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Indoline | C8H9N – PubChem

324-03-8, 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 324-03-8 as follows.

To a 250 mL round-bottom flask was added 6-fluoro-2,3-dihydro-lH-indole-2,3-dione (8 g, 48.45 mmol, 1.0 equiv.), iodomethane (15.1 g, 106.38 mmol, 2.2 equiv.), potassium carbonate (26.7 g, 193.18 mmol, 4.0 equiv.), and CH3CN ( 150 mL). The resulting mixture was stirred overnight at 60 C. The reaction was quenched with water. The resulting solution was extracted with ethyl acetate (100 mL x 3); and the combined organic layers were washed with brine (50 mL x 2), dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was purified via silica gel column chromatography eluting with ethyl acetate/petroleum ether (20%-40%) to give 6-fluoro-l-methyl-2,3-dihydro-lH-indole-2,3-dione 30b (7 g, 81%) as a red solid.

According to the analysis of related databases, 6-Fluoroindoline-2,3-dione, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARDELYX, INC.; CHAO, Jianhua; JAIN, Rakesh; HU, Lily; LEWIS, Jason Gustaf; BARIBAULT, Helene; CALDWELL, Jeremy; (249 pag.)WO2018/39384; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

324-03-8, A common compound: 324-03-8, name is 6-Fluoroindoline-2,3-dione, 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.

Mg(ClO4)2 (0.1 g) was added to a mixture of isatin (2 mmol), and dimedone (4 mmol) in aqueousethanol solution (50%, v/v, 5 mL), and the resulting mixture was stirred at 80C for 10-12 h. Upon completion of the reaction (TLC, Ethyl acetate/Petroleum ether = 1:4), the mixture was allowedto cool to room temperature. The resulting solid was filtered and washed successively with water(2 30 mL) and cold aqueous ethanol (2 1 mL) to afford a crude product, which was recrystallizedfrom EtOH to afford the pure product 3. Some insolubility could be observed in the refluxing ethanolduring the recrystallization process, which should be filtered when hot.

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, 6-Fluoroindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Chen, Chunfeng; Lv, Chunlei; Liang, Jianfeng; Jin, Jianqing; Wang, Lijun; Wu, Chunlei; Shen, Runpu; Molecules; vol. 22; 8; (2017);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

324-03-8, A common heterocyclic compound, 324-03-8, name is 6-Fluoroindoline-2,3-dione, molecular formula is C8H4FNO2, 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 mixture of 5.0 g (30.3 mmol) 6-fluoro-1 H-indole-2,3-dione in 75 mL of 33% aq. potassium hydroxide solution was added 4.67 g (53.0 mmol) pyruvic acid and this mixture was heated at 40 C for 18 hours. After cooling to room temperature 10% aq. sulfuric acid was added (pH about 1 ). The formed solid was isolated by filtration and dried in vacuum. The solid was the desired 7-fluoroquinoline-2,4-dicarboxylic acid, which was used without further purification. Yield: 6.02 g (85%) 1H-NMR (300 MHz, DMSO d6) delta (ppm) = 7.78 (ddd, 1 H), 7.99 (dd, 1 H), 8.42 (s, 1 H), 8.89 (dd, 1 H).

The synthetic route of 324-03-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BUCHMANN, Bernd; HEISLER, Iring; MUeLLER, Thomas; CLEVE, Arwed; HEROULT, Melanie; NEUHAUS, Roland; PETRUL, Heike; QUANZ-SCHOeFFEL, Maria; (194 pag.)WO2016/12474; (2016); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

A common heterocyclic compound, 324-03-8, name is 6-Fluoroindoline-2,3-dione, molecular formula is C8H4FNO2, 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. 324-03-8.

General procedure: The typical process for preparation of isatin-DHEAconjugates 4a-e is shown as following: To a solution of dehydroepiandrosterone-17hydrazone 3 (0.3 g, 1 mmol) inethanol (15 mL) was added the equal amounts of substituted isatin (1 mmol), which werestirred at ambient temperature or 50 oC and detected by thin-layerchromatography. Then the solution was concentrated, and the condensation product 4a-eseparated out on cooling (0-4 oC) and was recrystallized from ethanol. All the compounds were characterized by ESI-MS, 1HNMR spectroscopic data

The synthetic route of 6-Fluoroindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ke, Shaoyong; Shi, Liqiao; Yang, Ziwen; Bioorganic and Medicinal Chemistry Letters; vol. 25; 20; (2015); p. 4628 – 4631;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem