Month: August 2021

61-70-1, name is 1-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: 61-70-1

General procedure: An oven-dried reflux tube equipped with a magnetic stir bar and a Teflon stopcock was charged with aryl halide (1 mmol), oxindole (1 mmol),potassium carbonate (1.1 mmol), catalyst nanoparticles (0.05 mmol)and 1,4-dioxane (2 ml) and heated at 70 C. The mixture was vigorously stirred under these reaction conditions and completion of the reaction was monitored by TLC (EtOAc: n-hexane, 25:75). After completion of the reaction, the reaction mixture was cooled to room temperature, the magnetic nanoparticles of the catalyst were collected using a magnet. Ethyl acetate (5 mL) and water (10 mL)were added to the mixture in the next step. The aqueous layer was furtherextracted by ethyl acetate (2*5 mL). The combined organic layerswere washed with saturated brine, dried over CaCl2, filtered, and concentrated to give a residue which was purified by recrystallization from ethanol and water or by column chromatography on silica gelusing EtOAc: n-hexane, 1:7.

The synthetic route of 61-70-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Moghaddam, Firouz Matloubi; Tavakoli, Ghazal; Latifi, Fatemeh; Saeednia, Borna; Catalysis Communications; vol. 75; (2016); p. 37 – 41;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 317-20-4, 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. 317-20-4 name is 7-Fluoroisatin, 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: In a 25 mL round bottom flask, isatins 1 (1 mmol), 3-phenylisoxazol-5(4H)-one 2 (1 mmol) or 3-ethylisoxazol-5(4H)-one 7 (1 mmol), pyrazol-5-amine 3 (1 mmol) or 6-aminopyrimidine-2,4-(1H,3H)-dione 5 (1 mmol), and Amberlyst-15 (100 mg) were stirred in CH3OH (5.0 mL) at 80 C. When the reaction was completed (detected by TLC), the spherical catalyst was separated by a sieve at once under hot condition. Then, the reaction mixture was cooled to room temperature, and solid precipitation occurred. After filtration, the crude product was recrystallized from EtOH and DMF to give pure compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 7-Fluoroisatin, and friends who are interested can also refer to it.

Reference:
Article; Niu, Qingqing; Xi, Junhua; Li, Lei; Li, Li; Pan, Chengli; Lan, Meijun; Rong, Liangce; Tetrahedron Letters; vol. 60; 43; (2019);,
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. 16800-68-3, name is 1-Acetylindolin-3-one, A new synthetic method of this compound is introduced below., SDS of cas: 16800-68-3

The N- acetyl-3-indolyl-one 1.75g (10mmol), 1,2- dimethyl-indole 1.35g (10mmol) and cuprous iodide 0.19g (1.0mmol) was dissolved in ethanol, was heated to 60 C after 12 hours the reaction, extracted with dichloromethane, the organic layers combined, dried over anhydrous sodium sulfate, dichloromethane / methanol to give a white solid product was recrystallized from N- acetyl -3- (indol-3-methyl-N- ) – indole (2.8g, yield 92%),

The synthetic route of 16800-68-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sun Yat-sen University; Weng, Jiang; Lu, Gui; Guo, Jing; (7 pag.)CN105669516; (2016); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 169037-23-4, These common heterocyclic compound, 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, 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: A mixture of 5,6-dimethoxy-2-[(E)-1-arylmethylidene]-1-indanone (1, 0.364 mmol), thiazolidine-4-carboxylic (3, 0.364 mmol) and 1-morpholinoindoline-2,3-dione (2,0.364 mmol) was dissolved in methanol (1 mL) and irradiated for 2-3.5 min in a CEM microwave synthesizer (100 0C, 100 W). After completion of the reaction as evident from TLC, the mixture was poured into water. The precipitated solid was filtered and washed with water to afford the products 4a-i which was purified by recrystallisation.

The synthetic route of 169037-23-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Almansour, Abdulrahman I.; Ali, Sadath; Ali, Mohamed Ashraf; Ismail, Rusli; Choon, Tan Soo; Sellappan, Velmurugan; Elumalai, Karthi Keyan; Pandian, Suresh; Bioorganic and Medicinal Chemistry Letters; vol. 22; 24; (2012); p. 7418 – 7421;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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 675109-26-9 as follows. Application In Synthesis of 6-Bromoisoindolin-1-one

A mixture of 6-bromoisoindolin-1-one (1.0 g, 4.72 mmol), Pd(dppf)Cl2 (104 mg, 0.14 mmol), K2CO3 (1.96 g, 14.2 mmol) and 3-pyridylboronic acid (580 mg, 4.72 mmol) in dioxane (45 mL) and water (5 mL) was heated to 100 C. overnight. After cooling, the mixture was poured into water and extracted with EtOAc (3×100 mL). The combined organic fractions were washed with brine and dried over sodium sulfate. The solvent was evaporated and the residue was purified by column chromatography on silica gel (1%-50% EtOAc in pet. ether) to afford 85B (500 mg, 50% yield) as an off-white solid: 1H NMR (400 MHz, DMSO-d6) delta 8.94 (d, J=2 Hz, 1H), 8.67 (s, 1H), 8.60 (dd, J=4.8 Hz, 1.2 Hz, 1H), 8.16-8.13 (m, 1H), 7.96-7.94 (m, 2H), 7.71 (d, J=8.8 Hz, 1H), 7.52-7.49 (m, 1H), 4.44 (s, 2H); ESI m/z 211.0 [M+H]+.

According to the analysis of related databases, 675109-26-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Seal Rock Therapeutics, Inc.; BROWN, Samuel David; US2018/291002; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 19727-83-4,Some common heterocyclic compound, 19727-83-4, name is 6-Nitroindoline, molecular formula is C8H8N2O2, 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.

7-(2-methoxyethoxy)quinazolin-4-yloxy]phenyl}acetamide used as a starting material was prepared as follows :-Di-tert-butyl dicarbonate (7.2 g) was added to a mixture of 6-nitroindoline (4.92 g) and methylene chloride (50 ml) and the mixture was stirred at ambient temperature for 1 hour. 4-Dimethylaminopyridine (0.37 g) was added and the reaction mixture was stirred at ambient temperature for 16 hours. The resultant mixture was evaporated and the residue was purified by column chromatography on silica using increasingly polar mixtures of petroleum ether (b.p. 40-60C) and ethyl acetate as eluent. There was thus obtained tert-butyl 6-mtroindoline- 1-carboxylate as a solid (5.45 g); 1H NMR: (CDCl3) 1.6 (s, 9H), 3.2 (t, 2H), 4.1 (t, 2H), 7.2 (d, IH), 7.85 (d, IH), 8.3 (br s, 0.5H), 8.7 (br s, 0.5H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Nitroindoline, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/40520; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 16800-68-3, 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. 16800-68-3, name is 1-Acetylindolin-3-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: 1a (35.0 mg, 0.2 mmol, 1 equiv.), tert-BuOK (22.4 mg, 0.2 mmol, 1.0 equiv.) were added to a Schlenk tube. Then 2 ml THF was added using a syringe. The reaction mixture was stirred 15min,and then added iodonium salt 2 (0.2 mmol, 1.0 eq). The reaction was stirred at 30C for 10 hours.After cooling to room temperature, the solvent was removed in vacuo and the residue was purifiedby silica gel using a proper eluent (EtOAc/Hexane) to afford the desired products

The synthetic route of 1-Acetylindolin-3-one has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Yanxia; Han, Jianwei; Liu, Zhen-Jiang; Synlett; vol. 26; 18; (2015); p. 2593 – 2597;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 99365-40-9, A common heterocyclic compound, 99365-40-9, name is 6-Bromoindolin-2-one, molecular formula is C8H6BrNO, 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.

Commercially available 6-bromoxindole (656 mg), zinc cyanide (288 mg) and tetrakis triphenylphosphine palladium(0) (175 mg) were suspended in dry N,N-dimethylformamide (6 mL). The resulting mixture was degassed by three pump/vent cycles with argon and then placed in a preheated oil bath (80 C.). After stirring at this temperature for 15 h the mixture was cooled to room temperature, diluted with water (60 mL) and extracted with ethyl acetate (3×60 mL). The combined organic layers were washed with water (2×60 mL), dried (MgSO4), filtered and concentrated. The remaining residue was purified by flash chromatography (silica, dichloromethane/methanol) to afford the title compound (385 mg; 81%). [MH]+=159.

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; Alantos Pharmaceuticals, Inc.,; US2006/173183; (2006); 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. 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one, A new synthetic method of this compound is introduced below., COA of Formula: C10H9Cl2NO

5. Preparation of ZPR in the melt of Na C03 decahydrate. To the melt of Na2C03 decahydrate (40g) was added BITP HCl (lOg) and CEI (10.35g) and the mixture was heated at 95 C for 10 hours. After 10 h the conversion to ZRP was 88. 2% (% area by HPLC). To the reaction mixture water was added and the solid was filtrated and washed with water. After drying the solid weighs 17.14g (purity by HPLC 88%).; 7. Preparation of ZPR in the presence of NaCl. In a three necked flask was charged 40 ml brine, BITP HC1 (14. 1g), CEI (10.35g) and Na2C03 (14. 1g) ; the mixture was than heated at 90C for 16hours. After this the mixture was cooled, water was added and the solid was filtrated, washed with water and dried. The product weights after drying 16.9g (purity by HPLC 87.5%).

The synthetic route of 118289-55-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TEVA PHARMACEUTICAL INDUSTRIES LTD.; TEVA PHARMACEUTICALS USA, INC.; WO2005/40160; (2005); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 611-09-6, name is 5-Nitroindoline-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 611-09-6, Application In Synthesis of 5-Nitroindoline-2,3-dione

General procedure: Dimedone (0.280 g, 2 mmol) and isatin (0.147 g, 1 mmol) weremixed in oxalic acid: proline LTTM (5 mL) as solvent and the resultantmixture was heated at 90 C for appropriate time. After the completionof the reaction indicated by TLC, mixture was stirred at room temperatureand 5 mL distilled water was added. The insoluble crude productwas filtered, washed with distilled water and recrystallized from ethanolto obtain pure product.

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:
Article; Chandam; Patravale; Jadhav; Deshmukh; Journal of Molecular Liquids; vol. 240; (2017); p. 98 – 105;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem