Category: 169037-23-4

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. 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Product Details of 169037-23-4

Preparation of 3-hydroxy-5-trifluoromethoxy-3-(nitromethyl)indolin-2-one 5-trifluoromethoxy isatin ((0.115 g) and nitromethane (0.1 ml) were added to water and the reaction mixture was vigorously stirred at a temperature of 30 C. for 20 minutes. The obtained product was extracted with ethyl acetate and the solvent was removed to give pure product.

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

Reference:
Patent; RAO, Mandapati Mohan; PRATHIMA, Parvathaneni Sai; US2013/345438; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, 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. Computed Properties of C9H4F3NO3

General procedure: The title compound was synthesized in one step from commercially available starting materials according to the following procedure. Into a 20mL microwave reaction vial, containing a magnetic stir bar, were weighed 5-(trifluoromethoxy)isatin (460mg, 2.0mmol), K2CO3 (550mg, 4.0mmol), KI (33mg, 0.20mmol), followed by acetonitrile (20mL, 0.1M) and 2-bromoethyl phenyl ether (480mg, 2.4mmol). After being sealed with a crimp cap, the vessel was placed in a microwave reactor and heated to 160C for 10min, with magnetic stirring. After cooling to ambient temperature, the reaction was diluted with CH2Cl2 (?20mL) and washed with brine. The organic layer was separated and dried over Na2SO4. Solvent was removed under reduced pressure and the crude product was purified via flash column chromatography (silica gel, hexane/ethyl acetate, 0-50% ethyl acetate gradient). Product containing fractions were combined and the solvents removed under reduced pressure to obtain 583mg of ML326 (83% yield) as a red-orange powder. TLC Rf=0.79 (hexane/ethyl acetate 1:1); 1H NMR (400MHz, CDCl3 calibrated to 7.26) delta 7.52-7.46 (m, 2H), 7.31-7.25 (m, 3H), 6.98 (t, J=7.4Hz, 1H), 6.82 (d, 2H), 4.28 (t, J=5.0Hz, 2H), 4.17 (t, J=5.0Hz, 2H); 13C NMR (125MHz, CDCl3 calibrated to 77.16) delta 182.25, 158.27, 157.93, 150.01, 145.44, 131.02, 129.78, 121.75, 118.32, 114.39, 112.89, 65.94, 40.62; HRMS calcd for C17H13NO4F3[M+H+]; 352.0797 found: 352.0795.

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

Reference:
Article; Gentry, Patrick R.; Bridges, Thomas M.; Lamsal, Atin; Vinson, Paige N.; Smith, Emery; Chase, Peter; Hodder, Peter S.; Engers, Julie L.; Niswender, Colleen M.; Scott Daniels; Jeffrey Conn; Wood, Michael R.; Lindsley, Craig W.; Bioorganic and Medicinal Chemistry Letters; vol. 23; 10; (2013); p. 2996 – 3000;,
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. 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, A new synthetic method of this compound is introduced below., name: 5-(Trifluoromethoxy)indoline-2,3-dione

General procedure: A mixture of indoline-2,3-dione 1 (1mmol), l-tryptophan (2a) or l-histidine 2b (1mmol) and (E)-(2-nitrovinyl)benzene 3 (1.1mmol) was heated while stirred in [bmim]Br as the reaction medium (3mL) for 1hat 100C. After completion of the reaction (TLC), EtOAc (5mL) was added and the reaction mixture was stirred for 10min. This treatment was repeated and the combined ethyl acetate layers were removed in vacuo. The crude product was purified by recrystallization of the residue from EtOH (compounds 4) or by column chromatography (compounds 5). After extraction of the product, the ionic liquid was dried under vacuum at 80C for 2h to eliminate any water and could be reused for subsequent runs of the reaction.

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

Reference:
Article; Arumugam, Natarajan; Almansour, Abdulrahman I.; Kumar, Raju Suresh; Periasamy, Vaiyapuri Subbarayan; Athinarayanan, Jegan; Alshatwi, Ali A.; Govindasami, Periyasami; Altaf, Mohammad; Menendez, J. Carlos; Tetrahedron; vol. 74; 38; (2018); p. 5358 – 5366;,
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 169037-23-4 as follows. Computed Properties of C9H4F3NO3

Diethylcyanomethylphosphonate (279 mg, 1.58 mmol) was dissolved in dry THF (6 mL) at 0oC. Sodium hydride (66 mg, 1.15 mmol) was added and, to the resulting suspension, 5-trifluoromethoxyistain (347 mg, 1.50 mmol) was added slowly. Upon completion of the reaction as shown by TLC analysis, water (10 mL), brine (10 mL) and ethyl acetate (10 mL) were added and the aqueous layer extracted with ethyl acetate (3 x 5 mL) and dried with Na2SO4. The solvent was evaporated in vacuo and the resulting solid was purified by column chromatography (PSp:EtOAc 1:0 to 1:1) to yield a yellow product (31%), 1H NMR (400 MHz, CDCl3): d 6.39 (s, 1H), 6.91 (d, J 8.7, 1H), 7.26-7.31 (m, 1H), 7.84 (br s, 1H), 7.94 (d, J 1.9, 1H); 13C NMR (100 MHz, CDCl3): d 99.8, 111.3, 115.3, 118.9, 120.43 (q, J 258), 120.6, 126.9, 141.3, 142.5, 144.8 (q, J 2.1), 165.9; IR (neat, cm-1): 3254, 2228, 1760, 1728, 1624, 1473, 1245, 1124; HRMS: m/z: [M+Na]+ calcd for C11H5N2O2F3Na, 277.0195; found, 277.0188.

According to the analysis of related databases, 169037-23-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Davis, Holly J.; Kavanagh, Madeline E.; Balan, Tudor; Abell, Chris; Coyne, Anthony G.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 15; (2016); p. 3735 – 3740;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 5-(Trifluoromethoxy)indoline-2,3-dione

0.4 mmol of 5-trifluoromethoxyisatin, 0.2 mmol of antipyrine, 0.04 mmol of imidazole and 1 mL of water were mixed, and the reaction was stirred under an oil bath of 80 C for 29 hours.Then, the obtained reaction system was cooled to room temperature, extracted with dichloromethane, and the organic phase was collected. The obtained organic phase was dried over anhydrous sodium sulfate, concentrated, and separated by column chromatography (mobile phase: petroleum ether / ethyl acetate volume ratio) In the order of 4/1, 3/1, 2/1 and 1/1), the title compound I-7 (yellow solid, yield 65%, purity 99.8%) was obtained.

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 169037-23-4.

Reference:
Patent; Gannan Normal University; Zhang Yong; Nie Longjun; Liu Jinxiang; Fan Xiaolin; (23 pag.)CN110256407; (2019); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 169037-23-4

Step 1. Preparation of 2-amino-5-(trifluoromethoxy)benzoic Acid 5-(Trifluoromethoxy)isatin (15.0 g, 65 mmol) and potassium hydroxide pellets (4 g) were mixed in water (35 mL) and cooled to 0 C. With vigorous stirring, a solution of 30% aqueous hydrogen peroxide (11.7 g), potassium hydroxide pellets (5.8 g), and water (80 mL) was added drop-wise keeping the temperature below 10 C. After stirring 1 hour at 0 C., glacial acetic acid (22 mL) was added dropwise, causing foaming and formation of a precipitate. The contents were stirred overnight and filtered to afford the 2-amino-5-trifluoromethoxybenzoic acid as an amber solid (12.5 g, 87%). A small amount was recrystallized from ethyl acetate-hexanes to afford amber needles for an analytical sample and the remaining compound was used without further purification: mp 142.5-144.2 C. 1 H NMR (CDCl3, 300 MHz) 7.98 (s, 1H), 7.18 (d, 1H, J=8.0 Hz) 6.62 (d, 1H, J=8.0 Hz), 6.40 (brs, 2H). Anal. Calc’d for C8 H6 NO3 F3: C, 43.45; H, 2.73; N, 6.33. Found: C, 43.40; H, 2.65; N, 6.35.

According to the analysis of related databases, 169037-23-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; G.D. Searle & Co.; US6077850; (2000); A;,
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. 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, A new synthetic method of this compound is introduced below., Recommanded Product: 169037-23-4

Example 29 3-Cyclopentyl-2-(2,3-dioxo-5-trifluoromethoxy-2,3-dihydro-indol-1-yl)-N-pyrazin-2-yl-propionamide A stirred suspension of sodium hydride (60% dispersion in oil, 208 mg) in N,N-dimethylformamide (20 mL) at 0 C. was treated with a solution of 5-trifluoromethoxy-1H-indole-2,3-dione (1.0 g) in N,N-dimethylformamide. 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, 1.22 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. 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) to afford 3-cyclopentyl-2-(2,3-dioxo-5-trifluoromethoxy-2,3-dihydro-indol-1-yl)-propionic acid methyl ester (1.0 g, 60%).

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

Electric Literature of 169037-23-4, 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 169037-23-4 as follows.

General procedure: A mixture of bisarylidenepiperidin-4-one (1.36 mmoL), isatin (2.72 mmoL) and L-phenylalanine (2.72 mmoL) were heated with stirring in [bmim]Br medium (3 mL) for 1 h at 100 C. After completion of the reaction (TLC), ethyl acetate (2 x 5 mL) was added and the reaction mixture was stirred for 10 min. The organic layer was removed under reduced pressure and the crude product was purified by column chromatography (ethyl acetate:hexane v/v 3:7). 5′-Benzyl-4′-(o,p-dichlorophenyl)-5-(trifluoromethoxy)spiro[3,2′]oxindolopyrrolidino-4′-(o,p-dichlorophenyl-1?-styryl-5-benzylidene-spiro[3′.3?]piperidin-4?-one (5e): Melting point 288-290 C White solid, 94%; 1H-NMR (CDCl3, 400 MHz): delta/ppm 4.86 (d, J = 14.00 Hz, 1H), 4.68 (d, J = 13.92 Hz, 1H), 4.49-4.53 (m, 1H), 3.85 (d, J = 13.2 Hz, 1H), 3.58 (d, J = 16.82 Hz, 1H), 3.26 (d, J = 15.4 Hz, 1H), 2.95 (d, J = 13.96 Hz, 1H), 2.77-2.85 (m, 1H), 2.38 (d, J = 13.92 Hz, 1H), 6.49-6.59 (m, 2H), 6.00-7.76 (m, 19H, Ar); 13C-NMR (CDCl3, 100 MHz): delta/ppm 40.6, 46.3, 51.9, 52.3, 63.3, 65.5, 70.4, 99.3, 110.5, 121.8, 122.4, 123.9, 124.2, 126.4, 126.6, 126.5, 127.1, 128.4, 128.5, 128.6, 129.0, 129.2, 130.6, 132.4, 133.5, 134.2, 135.6, 135.8, 135.9, 136.8, 137.4, 138.1, 138.5, 132.9, 144.5, 177.8, 199.7. EI-MS: m/z 849 (M+). Anal. Calcd for C44H32Cl4F3N3O3: C, 62.21; H, 3.80; N, 4.95; Found: C, 62.36; H, 3.99; N, 4.83.

According to the analysis of related databases, 169037-23-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Arumugam, Natarajan; Almansour, Abdulrahman I.; Kumar, Raju Suresh; Govindasami, Periyasami; Al-thamili, Dhaifallah M.; Krishnamoorthy, Rajapandian; Periasamy, Vaiyapuri Subbarayan; Alshatwi, Ali A.; Mahalingam; Thangamani, Shankar; Menendez, J. Carlos; Molecules; vol. 23; 5; (2018);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C9H4F3NO3

Weigh5-trifluoromethoxy ruthenium0.95g (0.0041mol),0.85 g (0.0043 mol) of 4-chloroindole anhydride was added to a 100 ml three-necked flask containing a magnet, and then 40 ml of chloroform was added to the three-necked flask.1.5 ml of triethylamine, heated to reflux in an oil bath at 80 C for 3 h, after the reaction is over,The heating was stopped, and the mixture was cooled, and suction filtered to obtain a crude yellow solid powder.The product was washed 3 times with 10 ml of ethanol to obtain a pure product of a yellow solid powder.Dry and weigh 0.92g,The yield was 60.1%.

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 169037-23-4.

Reference:
Patent; Northwest University; Wang Cuiling; Bai Xiao; Zhang Xiaobin; Liu Jianli; (16 pag.)CN110143964; (2019); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products 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.

Weigh out 0.35 g (0.0015 mol) of 5-trifluoromethoxy ruthenium,0.39 g (0.0016 mol) of 5-bromoanthoic anhydride was added to a 100 ml three-necked flask containing a magnet, and then 40 ml of chloroform was added to the three-necked flask.1.5 ml of triethylamine, heated to reflux in an oil bath at 80 C for 3 h, after the reaction is over,The heating was stopped, and the mixture was cooled, and suction filtered to obtain a crude yellow solid powder.The product was washed 3 times with 10 ml of ethanol to obtain a pure product of a yellow solid powder.It was dried and weighed 0.45 g, and the yield was 72.6%

Statistics shows that 5-(Trifluoromethoxy)indoline-2,3-dione is playing an increasingly important role. we look forward to future research findings about 169037-23-4.

Reference:
Patent; Northwest University; Wang Cuiling; Bai Xiao; Zhang Xiaobin; Liu Jianli; (16 pag.)CN110143964; (2019); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem