Category: indolines-derivatives

Synthetic Route of 39603-24-2,Some common heterocyclic compound, 39603-24-2, name is 5,7-Dimethylindoline-2,3-dione, molecular formula is C10H9NO2, 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 isatins 1a-g (1 mmoL) with an equimolar amount of N,N’-diphenyl/(p-tolyl)thiourea2a,b (1 mmoL) and bromoacetic acid 3 (0.14 g, 1 mmoL) in glacial acetic acid (10 mL) in the presenceof sodium acetate (0.16 gm, 2 mmoL), was heated under reflux for 3 h. The formed solid was filteredoff while hot, washed with hot ethanol, dried and recrystallized from DMF to furnish the targethybrids 4a-n.

The synthetic route of 39603-24-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; El-Naggar, Mohamed; Eldehna, Wagdy M.; Almahli, Hadia; Elgez, Amr; Fares, Mohamed; Elaasser, Mahmoud M.; Abdel-Aziz, Hatem A.; Molecules; vol. 23; 6; (2018);,
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Some common heterocyclic compound, 317-20-4, name is 7-Fluoroisatin, 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. Formula: C8H4FNO2

General procedure: Sulfonated-beta-cyclodextrin (beta-CD-SO3H) (76 mg, 0.06 mmol) was dissolved in water (5 mL) at RT by stirring to get the clear solution in 50 mL round bottom ask. Further, isatin 2 (0.31 mmol) and tryptamine 1a/isotryptamine 1b (0.31 mmol) were added to the solution under constant stirring and mixture was heated at 80 C for 8-12 h. The progress of the reaction was monitored by TLC. After completion of reaction, it was cooled to room temperature, water was added to it. The aqueous phase was extracted with ethylacetate. The organic extracts were combined, washed with brine and dried over sodium sulfate. The solvent was evaporated in vacuo and the crude product obtained was puried by column chromatography using chloroform/methanol (99:1) as an eluent furnishing the product. The spectral and analytical data of all the reported products is consistent with the previous (6c,d,f) reports.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 317-20-4, its application will become more common.

Reference:
Article; Urmode, Tukaram D.; Dawange, Monali A.; Shinde, Vaishali S.; Kusurkar, Radhika S.; Tetrahedron; vol. 73; 30; (2017); p. 4348 – 4354;,
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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. 3485-84-5, name is N-Vinylphthalimide, A new synthetic method of this compound is introduced below., Recommanded Product: N-Vinylphthalimide

3-Amino-5-bromobenzotrifluoride (2.00 g, 8.332 mmol) was dissolved in acetonitrile (80 mL) and the solution was degassed with nitrogen. Pd(OAc)2 (94 mg, 0.417 mmol), tris(2- methylphenyl)phosphine (254 mg, 0.833 mmol) and triethylamine (3.5 mL, 25.0 mmol) were added and the bright orange solution was allowed to stir at room temperature for 1 h. To this solution was added N-vinylphthalimide (1.73 g, 10.0 mmol) and the reaction mixture was degassed and was heated at reflux for 16 h. The reaction was filtered through a Celite pad. The filtrate was washed with water and brine, was dried over magnesium sulfate, was filtered and was concentrated. The residue was purified by column chromatography (eluted with hexanes:ethyl acetate = 3 : 1 to 2: 1 to 1 : 1) to afford 2- {(E)-2-[3-amino-5- (trifluoromethyl)phenyl]vinyl}-lH-isoindole-l,3(2H)-dione (2.02 g, 73% yield) as a yellow solid. XH NMR (400 MHz, CDC13): delta 7.92-7.90 (m, 2H), 7.78-7.76 (m, 2H), 7.59 (d, 1H), 7.35 (d, 1H), 7.09 (s, 1H), 6.91 (s, 1H), 6.79 (s, 1H), 3.88 (-NH2; br s, 2H).

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; EXELIXIS, INC.; ANAND, Neel, Kumar; BROWN, S., David; TESFAI, Zerom; ZAHARIA, Cristiana, A.; WO2012/37132; (2012); A1;,
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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. 143262-20-8, name is 1-(tert-Butoxycarbonyl)indoline-7-carboxylic acid, A new synthetic method of this compound is introduced below., Quality Control of 1-(tert-Butoxycarbonyl)indoline-7-carboxylic acid

A mixture of 1-(tert-butoxycarbonyl)indoline-7-carboxylic acid (460 mg, 1.75 mmol), MeI (0.22 mL, 3.5 mmol) and potassium carbonate (484 mg, 3.5 mmol) in acetone (20 mL) was heated at 60 C. After the reaction was complete, the reaction mixture was filtered through celite, eluted with dichloromethane and concentrated in vacuo. The residue was purified by silica gel chromatography with hexanes:ethyl acetate to give 1-tert-butyl 7-methyl indoline-1,7-dicarboxylate (390 mg, 80%).

The synthetic route of 143262-20-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; Gray, Nathanael S.; Waller, David; Choi, Hwan Guen; Wang, Jinhua; Deng, Xianming; (104 pag.)US2016/24115; (2016); A1;,
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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. 875003-43-3, name is 7-Fluoro-1-methylindoline-2,3-dione, A new synthetic method of this compound is introduced below., Computed Properties of C9H6FNO2

General procedure: A solution of 6-fluoro-1-methylindolin-2-one (Step B12.2) (255 mg, 1.235 mmol) in DMF (10 ml.) was cooled down to 0C and NBS (286 mg, 1.606 mmol) was added. The resulting mixture was allowed to warm up to RT then, heated up and stirred at 80C for 2 hr. The reaction mixture was diluted with EtOAc and washed with aqueous NaHC03 solution, 0.1 M LiBr and brine. The organic layer was dried over MgS04, filtered and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel (cyclohexane / 20 to 100% EtOAc) to afford the title product (222 mg, 0.591 mmol, 47.9% yield). Rt = 0.87 min (UPLC-MS); ESI-MS = 243.9 / 245.9 [M+1] + (UPLC-MS).

The synthetic route of 875003-43-3 has been constantly updated, and we look forward to future research findings.

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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Electric Literature of 64483-69-8, 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. 64483-69-8, name is 5-Acetylindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 40 A solution of 5-acetyloxindole (352 mg, 2 mmol), (EP 0155828 A2), in DMF (5 ml) was added to a suspension of sodium hydride (80 mg, 2 mmol, prewashed with hexane) in DMF (1 ml) and the mixture stirred for 30 minutes at ambient temperature. 4-Chloro-6-methoxy-7-(2-methoxyethoxy)quinazoline (180 mg, 0.67 mmol), (prepared as described for the starting material in Example 2), was added and the mixture was heated at 50 C. for 1.5 hours. The mixture was partitioned between water and ether and the aqueous layer was adjusted to pH7 with 2M hydrochloric acid. The precipitate was collected by filtration, washed with water and dried under vacuum. The solid was dissolved in methylene chloride/methanol (30 ml/30 ml) and 7M ethanolic hydrogen chloride (1 ml) was added. The mixture was left to stand for 15 minutes at ambient temperature, the resulting precipitate was collected by filtration, washed with ether and dried under vacuum to give 4-(5-acetyloxindol-3-yl)-6-methoxy-7-(2-methoxyethoxy)quinazoline hydrochloride (195 mg, 71%). 1H NMR Spectrum: (DMSOd6, CF3CO2D) 2.52(s, 3H); 3.37(s, 3H); 3.80(t, 2H); 3.85(s, 1H); 4.35(t, 2H); 7.09(d, 1H); 7.33(s, 1H); 7.78(s, 1H); 7.88(d, 1H); 8.25(s, 1H); 8.85(s, 1H). MS-ESI: 408 [MH]+

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

Reference:
Patent; Zeneca Limited; US6265411; (2001); B1;,
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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. 59-48-3, name is Indolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C8H7NO

5-Iodo-2-oxindole 2-Oxindole (82.9 g) was suspended in 630 mL of acetic acid with mechanical stirring and the mixture cooled to 10 C. in an ice water bath. Solid N-iodosuccinimide (175 g) was added in portions over 10 minutes. After the addition was complete the mixture was stirred for 1.0 hour at 10 C. The suspended solid, which had always been present, became very thick at this time. The solid was collected by vacuum filtration, washed with 100 mL of 50% acetic acid in water and then with 200 mL of water and sucked dry for 20 minutes in the funnel. The product was dried under vacuum to give 93.5 g (36%) of 5-iodo-2-oxindole containing about 5% 2-oxindole by proton NMR.

The synthetic route of 59-48-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sugen, Inc.; US6878733; (2005); B1;,
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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 2058-74-4 as follows. name: 1-Methylisatin

General procedure: A solution of N-methylisatin (322 mg, 2.0 mmol), phenylacetylene (306 mg, 3.0 mmol), CuI (76 mg, 0.4 mmol), and Cs2CO3 (978 mg, 3.0 mmol) in CH3CN (4.0 mL) was stirred at room temperature for 18 h. After aqueous extractive workup and column chromatographic purification process (CH2Cl2/EtOAc, 15:1) 1a was obtained as a pale yellow solid, 347 mg (66%).1-12 Other compounds were prepared similarly,1-12 and the propargylic alcohols were used in the next hydrogenation step without further identification process.

According to the analysis of related databases, 2058-74-4, the application of this compound in the production field has become more and more popular.

Reference:
Note; Seo, Da Young; Min, Beom Kyu; Roh, Hwa Jung; Kim, Jae Nyoung; Bulletin of the Korean Chemical Society; vol. 38; 10; (2017); p. 1231 – 1234;,
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Reference of 20870-78-4,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.

5-Bromo-2-oxindole (10 g, 47 mmol), 7.4 g (61 mmol) of benzeneboronic acid, 4.0 g (3.5 mmol) of tetrakis(triphenylphosphine)palladium(0), 17 g (160 mmol) of anhydrous sodium carbonate, 100 mL of toluene and 100 mL of ethanol were refluxed for 18 hours. The mixture was vacuum filtered hot to remove insolubles. The organic layer of the filtrate was separated while hot and concentrated. The solids were collected by vacuum filtration and washed with 5 mL of ethanol. The solids were triturated with 1 N hydrochloric acid, collected by vacuum filtration, washed with water and dried under vacuum. The crude solids were triturated with dichloromethane and dried under vacuum to give 8.3 g (63% yield) of the title compound. 1H-NMR (dimethylsulfoxide-d6) delta10.00 (s, 1H), 7.20-6.80 (multiplets, 9H), 3.50 (s, 3H).

The synthetic route of 20870-78-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUGEN, Inc.; US2004/186160; (2004); 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 366452-98-4 as follows. Safety of 4-Amino-2,3-dihydro-1H-isoindol-1-one

l Synthesis of isoindolinone (25): The suspension of 2,3-dihydro-1H-isoindol-1-one 4 (0.100 gm, 0.61 mmol.) in ethyl acetate and aq. NaHCO3 solution, was added m-nitrobenzoyl chloride (0.15 mg, 0.81 mmol.) at room temperature. The reaction mixture was stirred at room temperature for 30 min, and solid separated was filtered and dried under vacuum to give 2,3-dihydro-1H-isoindol-1-one 25 (0.041 gm, 36%).

According to the analysis of related databases, 366452-98-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Jagtap, Prakash; Southan, Garry; Salzman, Andrew; Szabo, Csaba; Ram, Siya; US2002/95044; (2002); A1;,
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