Month: July 2021

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. 264916-06-5, name is tert-Butyl 5-aminoisoindoline-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 264916-06-5

Step-1: Synthesis of tert-butyl 5-((1-(6-(tert-butyl)pyridin-2-yl)-2-ethyl-3-oxo-2,3-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)amino)isoindoline-2-carboxylate To a stirred solution of 1-(6-(tert-butyl)pyridin-2-yl)-2-ethyl-6-(methylthio)-1,2-dihydro-3H-indazol-3-one (200 mg, 0.582 mmol, 1.0 eq) in (2.0 mL) of toluene was added m-CPBA (287 mg, 1.164 mmol, 2.0 eq) and allowed to stir at rt for 30 minutes. tert-butyl 5-aminoisoindoline-2-carboxylate (164 mg, 0.698 mmol, 1.2 eq) and DIPEA (0.40 mL, 2.328 mmol, 4.0 eq) were added and allowed to stir at rt for overnight. The formation of precipitates were observed which were filtered to afford the desired compound tert-butyl 5-((1-(6-(tert-butyl)pyridin-2-yl)-2-ethyl-3-oxo-2,3-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)amino)isoindoline-2-carboxylate (135 mg, 43.83%) as brown solid.

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 264916-06-5.

Reference:
Patent; giraFpharma LLC; Chakravarty, Sarvajit; PHAM, Son Minh; Kankanala, Jayakanth; AGARWAL, Anil Kumar; PUJALA, Brahmam; SONI, Sanjeev; ARYA, Satish K.; PALVE, Deepak; Gupta, Ashu; KUMAR, Varun; (498 pag.)US2019/106427; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 56341-37-8, 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. 56341-37-8, name is 6-Chlorooxindole belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 59 Preparation of intermediate E/Z-2-[4-chloro-2-(6-chloro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-phenoxy]-2-methyl-propionic acid tert-butyl ester To a mixture of 2-(4-chloro-2-formyl-phenoxy)-2-methyl-propionic acid tert-butyl ester (5.17 g, 17.3 mmol) and 6-chlorooxindole (2.89 g, 17 3 mmol) were anhydrous methanol (100 mL) at room temperature was slowly added piperidine (1.7 mL, 17.3 mmol). The reaction mixture was heated at 70 C. for 0.5 h. Then the mixture was cooled to room temperature and filtered. The precipitate was dried and collected to give E/Z-2-[4-chloro-2-(6-chloro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-phenoxy]-2-methyl-propionic acid tert-butyl ester as a yellow solid (Yield 6.5 g, 84%).

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-Chlorooxindole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Zhang, Jing; Zhang, Zhuming; US2010/210674; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 22190-33-6, name is 5-Bromoindoline, 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 22190-33-6, Quality Control of 5-Bromoindoline

Step A: tert-Butyl 5-bromo-2,3-dihvdro-lH-indole-l-carboxylate To a stirred solution of 5-bromoindoline (320 mg, 1.62 mmol) in THF (8 mL) was added di-tert-butyl dicarbonate (529 mg, 2.42 mmol) and the resulting mixture was stirred at ambient temperature for 18 h. The reaction mixture was concentrated in vacuo and the residue was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc – 100:0 to 90:10, to give the title compound.

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; BELL, Ian, M.; ZHAO, Lianyun; FRALEY, Mark; ZHU, Cheng; BIFTU, Tesfaye; BRNARDIC, Edward Joseph; WANG, Cheng; ZARTMAN, C. Blair; GALLICCHIO, Steven; NGUYEN, Diem; CROWLEY, Brendan; POTTEIGER, Craig; (257 pag.)WO2016/22644; (2016); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 6780-38-7, A common heterocyclic compound, 6780-38-7, name is 2-(1,3-Dioxoisoindolin-2-yl)acetyl chloride, molecular formula is C10H6ClNO3, 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 stirred solution of 3 (10.00 g, 54.57 mmol) and triethylamine (15.21 mL, 109.10mmol) in 200 mL CHCl3 at 5-10 C a solution of phthalylglycyl chloride 4 (14.64 g, 65,48 mmol) in CHCl3 (50 mL) was added dropwise over 30 min. During the chlorideaddition the product precipitated. The mixture was stirred additionally at 24 oC for 30min and then chloroform (1.50 L) was added to completely dissolve the product. Theorganic phase was washed with water (300 mL), 5% sodium carbonate solution (300mL) and water (300 mL) and dried over MgSO4. The solution was concentrated invacuo to 1/3 of the initial volume and after cooling to 10 C the precipitated productwas filtered off to give 17.60 g (87%) of product 5 as pale beige solid; mp = 234-235C. IR (KBr): 3269, 3063, 3026, 1772, 1732, 1666, 1587, 1541, 1413, 1257, 1211,952, 715 cm-1; 1H NMR (500 MHz, CDCl3): delta 3.99 (s, 2 H), 4.30 (s, 2 H), 7.05-7.18(m, 7 H, Ar), 7.22-7.30 (m, 2H, Ar), 7.75-7.77 (m, 2 H, Ar), 7.85-7.87 (m, 2 H, Ar); 13C NMR (125 MHz, CDCl3): delta 38.3, 41.6, 123.8, 124.1, 125.8, 126.7, 127.7, 128.1,128.9, 128.9, 131.0, 131.4, 131.9, 134.3, 135.1, 138.7, 164.2, 167.6; HRMS (ESI):m/z calcd for C23H18N2O3Na [M+Na]+: 393.1215; found: 393.1223.

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:
Article; Roszkowski, Piotr; Maurin; Czarnocki, Zbigniew; Beilstein Journal of Organic Chemistry; vol. 11; (2015); p. 1509 – 1513;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 3891-07-4, name is 2-(2-Hydroxyethyl)isoindoline-1,3-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 3891-07-4, category: indolines-derivatives

To a solution of N-(2-hydroxyethyl)phthalimide (2g, 10.5mmol) in anhydrous tetrahydrofuran (30mL) was added 60% NaH (0.84 g, 21 mmol) at -5C. The mixture was stirred at the same temperature for 20 min. Commercially available 4b (1.5 mL, 12.6 mmol) was added to the mixture and was stirred at the same temperature for 30 min and then stirred at room temperature for 4 h and filtered. The filtrate was concentrated under reduced pressure to give 5b (2.65 g, 90%) as a off-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, 2-(2-Hydroxyethyl)isoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Wang, Minghua; Ye, Cheng; Liu, Mingliang; Wu, Zhaoyang; Li, Linhu; Wang, Chunlan; Liu, Xiujun; Guo, Huiyuan; Bioorganic and Medicinal Chemistry Letters; vol. 25; 14; (2015); p. 2782 – 2787;,
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 59-48-3 as follows. name: Indolin-2-one

5-Acetyl-3-(3-methyl-1H-indol-2-ylmethylene)-1,3-dihydro-indol-2-one 2-Oxindole (3 g) was suspended in 1,2-dichloroethane and slowly treated with 3.2 mL of acetyl chloride. The resulting suspension was heated to 50 C. for 5 hours, cooled, and poured into water. The resulting precipitate was collected by vacuum filtration, washed copiously with water and dried under vacuum to give 2.9 g (73% yield) of 5-acetyl-2-oxindole as a brown solid. 1H NMR (360 MHz, DMSO-d6) delta10.75 (s, br, NH), 7.83 (d, J=8 Hz, 1H), 7.78 (s, 1H, H-4), 6.88 (d, J=8 Hz, 1H), 3.53 (s, 2H, CH2), 2.49 (s, 3H, CH3).

According to the analysis of related databases, 59-48-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SUGEN, Inc.; US2002/183364; (2002); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 89-40-7, 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. 89-40-7, name is 5-Nitroisoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: In a typical experiment, a mixture of nitroarene compound (1.0 mmol),ammonium formate (3.3 mmol, 208 mg, 1.1 equivalent), palladium catalyst (10 % Pdon activated carbon, 2 mol%, 21 mg) and silica (175 mg) was ball milled in thepresence of dry methanol (eta = 0.25 muL mg-1) for 90 minutes. After milling, a smallsample (? 1 mg) of the crude reaction mixture was suspended in methanol andimmediately analyzed by TLC (typically using dichloromethane : methanol = 20 : 1mixture as an eluent). The crude mixture was left in a well ventilated hood overnight,suspended in methanol and filtered over a Buechner funnel. Evaporation of the filtrateafforded the desired amino-derivative. If necessary, the final product was purified bycolumn chromatography.

The synthetic route of 5-Nitroisoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Portada, Tomislav; Margeti?, Davor; ?trukil, Vjekoslav; Molecules; vol. 23; 12; (2018);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. category: indolines-derivatives

General procedure: To a solution of 1a (35 mg, 0.2 mmol) and 2a (52.4 mg,0.4 mmol) in DCE (3 mL) was added iodine (10 mg, 0.04 mmol). The reaction mixture was heated at 80 C for 24 h, then cooled to room temperature and quenched with saturated sodium thiosulfate. The mixture was extracted with CH2Cl2, the combined organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel to afford title compound.

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

Reference:
Article; Guo, Jing; Weng, Jiang; Huang, Gong-Bin; Huang, Lin-Jie; Chan, Albert S.C.; Lu, Gui; Tetrahedron Letters; vol. 57; 49; (2016); p. 5493 – 5496;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 112656-95-8, A common heterocyclic compound, 112656-95-8, name is 7-Nitroindoline-2,3-dione, molecular formula is C8H4N2O4, 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: Mg(ClO4)2 (10 mol %) was added to a mixture of isatin (2 mmol), malononitrile or ethyl cyanoacetate (2mmol), and dimedone (2 mmol) in aqueous ethanol solution(50%, v/v, 5 mL), and the resulting mixture was stirred at 50C for 30-60 min. Upon completion of the reaction (TLC),the mixture was allowed to 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 pure product 4.

The synthetic route of 112656-95-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wu, Chunlei; Shen, Runpu; Chen, Jianhui; Hu, Chunqi; Bulletin of the Korean Chemical Society; vol. 34; 8; (2013); p. 2431 – 2435;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 611-09-6, 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. 611-09-6, name is 5-Nitroindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a mixture containing isatin derivatives (1 mmol),malononitrile or ethyl cynocette (1mmol) and 1,3-cyclldiketone (1 mmol) in water (5 mL), H-Fe3O4(at)DA-SO3H(0.01g) were added and stirred under reflux condition. The progress of the reaction was monitored by TLC (n-hexane:EtOAc 7:3). After completion of the reaction the mixture was cooled and the catalyst was separated by means of an external magnet from mixture, then the crude product was collected and washed with distilled water and dried. They were weighted for reporting of the yields.

The synthetic route of 5-Nitroindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mirhosseyni, Marzie Sadat; Nemati, Firouzeh; Elhampour, Ali; Combinatorial Chemistry and High Throughput Screening; vol. 21; 7; (2018); p. 487 – 494;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem