Category: indolines-derivatives

Adding a certain compound to certain chemical reactions, such as: 317-20-4, name is 7-Fluoroisatin, 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 317-20-4, HPLC of Formula: C8H4FNO2

General procedure: Indoles (0.20mmol), isatins (0.10mmol), and 60 wt%PWA/MCM-41 catalyst (0.0050 g) were stirred in THF(0.3mL) at room temperature for 2.5 h and monitored byTLC. The product were purified by column chromatographyon silica gel using petroleum ether/ethyl acetate (20 : 1, 10 : 1,5 : 1, 2 : 1, 1 : 1) as the eluent. All compounds (3a-3o) werecharacterized by 1H and 13C NMR (400MHz) spectral analysis.The catalyst was separated from the reaction mixture bycentrifugalization, dried at 473K for 4 h after washing withethanol, then continued to be reused for the next reaction.

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; Xing, Liuzhuang; Hui, YongHai; Yang, Jinghui; Xing, Xuejian; Hou, Yadong; Wu, Yang; Fan, Kui; Wang, Wei; Journal of Chemistry; vol. 2018; (2018);,
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Related Products of 25369-33-9, 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 25369-33-9 as follows.

General procedure: A reaction mixture of the proper substituted indolin-2-ones 6,aldehyde (1.2 eq.), and piperidine (0.1 eq.) in ethanol (1 mL/0.5 mmol oxindole) was refluxed for 3-5 h, under nitrogen atmosphere. After, the mixture was cooled and put on ice, where the product precipitated. The product was filtered in vacuum with cold ethanol [10,14-17]. Finally, the product was placed in the vacuum desiccators to give the expected compound. The indolin-2-ones 3e was generated through substituted isatin in the presence of hydrazine monohydrate and ethylene glycerol, under reflux [18].

According to the analysis of related databases, 25369-33-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Nunes, Rute C.; Ribeiro, Carlos J.A.; Monteiro, Angelo; Rodrigues, Cecilia M.P.; Amaral, Joana D.; Santos, Maria M.M.; European Journal of Medicinal Chemistry; vol. 139; (2017); p. 168 – 179;,
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Adding a certain compound to certain chemical reactions, such as: 18711-13-2, name is 4,7-Dichloroindoline-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 18711-13-2, category: indolines-derivatives

4,7-Dichloro-3-(2-(4-cyclopropyl-2-fluorophenyl)-2-oxoethyl)-3-hydroxyindolin-2- one (EXAMPLE 18): To 4,7-dichloroindoline-2,3-dione (A) ( 261 mg, 1.21 mmol) in 15 mL of methanol were l-(4-cyclopropyl-2-fluorophenyl)ethanone (B) (280 mg, 1.57 mmol) and 10 drops of diethylamine (2). The reaction was stirred at 50C for 24 hours. The solvent was removed and the residue was purified with flash chromatography (0-5% Methanol/CH2C12) to get an off white solid. 4,7-Dichloro-3-(2-(4-cyclopropyl-2-fluorophenyl)-2-oxoethyl)-3- hydroxyindolin-2-one (EXAMPLE 18): off-white solid; 1H NMR (DMSO-d6, 400 MHz) delta 0.82 (m, 2H), 1.07 (m, 2H), 2.01(m, 1H), 3.66 (d, 1H, J=16 Hz), 4.26 (d, 1H, J=16Hz), 6.44(s, 1H), 6.91(d, 1H, J=8Hz), 7.01 (m, 2H), 7.31 (d, 1H, J=8Hz), 7.57(m, 1H), 10.96 (s, 1H). Chiral separation was performed by a method substantially similar to the method described above. LC screening was performed with: column: RegisCell, 250 mm x 4.6 mm, 5 mum, hexane/IPA (80/20), 1.5 ml/min, injection volume: 2.0 mu, pressure: 51.5 bar. Peak 1 : retention time: 5.16 min, width: 0.238 min, area: 3716.20, area %: 49.78. Peak 2: retention time: 6.49 min, width: 0.324 min, area: 3749.55, area %: 50.22.

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; TOKALAS, INC.; VERNIER, Jean-michael; (82 pag.)WO2016/57698; (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. 366453-22-7, name is 4-Methoxyisoindolin-1-one, A new synthetic method of this compound is introduced below., category: indolines-derivatives

Step c: To an ice-cold solution of [11C] (291 mg, 1.78 [MMOL)] in CH2CI2 (20 mL) was added a 1.0 M BBr3 solution in [CH2CI2] (3.6 mL, 3.6 [MMOL).] The cold bath was then removed and the resulting solution was stirred for 16 h at ambient temperature. The reaction was carefully quenched by the addition of water and the mixture was extracted with EtOAc. The combined extracts were washed with water and brine, dried [(MGS04),] filtered and evaporated to dryness to give [11D] (232 mg, 87% yield) as beige solid.

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; BOEHRINGER INGELHEIM (CANADA) LTD.; WO2004/26875; (2004); A1;,
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Electric Literature of 39755-95-8, 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 39755-95-8 as follows.

EXAMPLE 21 8-Methoxyindolo[2,1-b]quinazoline-6,12-dione STR29 Using the procedure in Example 12 and substituting isatoic anhydride for 5-chloroisatoic anhydride and 5-methoxyisatin for 5-fluoroisatin gave the title compound in 24% yield: mp 267.6-269 C.; 1 H NMR (300 MHz, DMSO-d6) delta 8.28 (d, 1H) 8.25 (d, 1H) 7.93 (d, 2H) 7.68-7.78 (m, 1H) 7.37-7.46 (m, 2H) 3.88 (s, 3H); MS (M+H)+ 279.

According to the analysis of related databases, 39755-95-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PathoGenesis Corporation; US5441955; (1995); A;,
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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 32372-82-0 as follows. category: indolines-derivatives

Isoindoline hydrochloride (31.1 mg, 0.2 mmol), graphene oxide (8 mg),And a stirrer is placed in the reaction tube, after replacing the inert gas,Add 1 ml of DMF and seal the reaction tube. Place the reaction tube at 150CIn the oil bath, stir the reaction for 18 hours; after cooling to room temperature,The catalyst was removed by filtration and the filtrate was diluted with 15 mL of water.And extracted with ethyl acetate 3 times, each time 15mL; combined extract,Dry with anhydrous sodium sulfate and filter. The filtrate is concentrated under reduced pressure.The crude product was purified by column chromatography with ethyl acetate:petroleum ether=1:3 (containing 1% triethylamine) as eluent. Black oil, 42% yield

According to the analysis of related databases, 32372-82-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Xiangtan University; Gong Xing; Xie Guilin; Cai Changqun; Zhang Jingyu; (19 pag.)CN107827816; (2018); A;,
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Related Products of 24566-79-8, The chemical industry reduces the impact on the environment during synthesis 24566-79-8, name is N-(6-Bromohexyl)phthalimide, I believe this compound will play a more active role in future production and life.

General procedure: Amixture of the corresponding secondary amine 7a-d (5.5 mmol), anhydrous K2CO3 (6 mmol) andcompounds 2-4 (5 mmol) was added inCH3CN (20 ml). The mixture was heated at 65 C for 8-10 h. Thesolvent was evaporated under reduced pressure. Then water (25 mL) was added,and the mixture was extracted with dichloromethane (20 mL ¡Á 3). The combinedorganic phases were washed with saturated aqueous NaCl (30 mL), dried oversodium sulfate, and filtered. The solvent was evaporated under a vacuum. The residue was purified on a silicagel chromatography using mixtures of petroleum/acetone as eluent to obtain theoil products 8-10.

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, N-(6-Bromohexyl)phthalimide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Pan, Wanli; Hu, Ke; Bai, Ping; Yu, Lintao; Ma, Qinge; Li, Tao; Zhang, Xu; Chen, Changzhong; Peng, Kelin; Liu, Wenmin; Sang, Zhipei; Bioorganic and Medicinal Chemistry Letters; vol. 26; 10; (2016); p. 2539 – 2543;,
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25369-33-9, name is 7-Chloroindolin-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. category: indolines-derivatives

General procedure: To a 25 mL round bottomed flask was added different substituted oxindoles 8 (0.2 mmol, 1.0 equiv.) and bromoethylsulfonium salt 9 (132.99 mg, 0.3 mmol, 1.5 equiv.), DMF (2 mL). The mixture was stirred at room temperature for 5min and Et3N (61.88 mg, 0.6 mmol, 3.0 equiv.) was added into reaction system. The mixture was stirred for 6h at room temperature until the reaction completed, quenched with saturated ammonium chloride solution (5 mL), and was extracted with EtOAc (3¡Á30 mL). The combined organic layer washed with H2O (2¡Á10 mL), dried with anhydrous sodium sulfate. After concentration, product was purified using column chromatography on silica gel with suitable eluent.

The synthetic route of 25369-33-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Qin, Hui; Miao, Yuanyuan; Zhang, Ke; Xu, Jian; Sun, Haopeng; Liu, Wenyuan; Feng, Feng; Qu, Wei; Tetrahedron; vol. 74; 47; (2018); p. 6809 – 6814;,
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Some common heterocyclic compound, 3891-07-4, name is 2-(2-Hydroxyethyl)isoindoline-1,3-dione, molecular formula is C10H9NO3, 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. HPLC of Formula: C10H9NO3

To a suspension of 3.0 g (7.84 mmol) of pyrimidinone A, 4.12 g (15.7 mmol) of triphenylphosphine and 4.12 g (15.7 mmol) of N-(2-hydroxyethyl)-phthalimide in 45 ML of 1,4-dioxane at 5 C. was added dropwise a solution of 2.73 g (2.5 ML, 15.7 mmol) of diethylazodicarboxylate in 10 ML of 1,4-dioxane over a period of 20 min. through an additional funnel.The suspension was stirred at 5 C. for 1 hour and then at room temperature overnight at which point the suspension turned into a yellow solution.The solution was concentrated in vacuo and the residue was purified by column chromatography with silica eluding with 7.5% ethyl acetate in dichloromethane affording 3.92 g of the phthalimide 1 (90% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3891-07-4, its application will become more common.

Reference:
Patent; Goldstein, David Michael; Hawley, Ronald Charles; Lui, Alfred Sui-Ting; Sjogren, Eric Brian; US2003/232847; (2003); A1;,
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Related Products of 24566-79-8, A common heterocyclic compound, 24566-79-8, name is N-(6-Bromohexyl)phthalimide, molecular formula is C14H16BrNO2, 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.

11.9 g tritylsulfide 32 (43.1 mmol, 1.02 eq) were dissolved in 50 mL DMSO. 7.30 mL DBU (48.8 mmol; 1.14 eq) and 13.3 g phthalimide 31 followed by 15 mL DMSO were added. The mixture was stirred for 12 min at ambient temperature. 700 mL ethyl acetate and 200 mL 0.1 N HCl were added. The mixture was stirred until both solvent layers were clear. The layers were separated. The aqueous phase was extracted with ethyl acetate (3x, 50 mL each). The organic solutions were combined, washed with 80 mL sat. NaHC03and 80 mL brine, dried over Na2S04and filtered. The solvent was removed in vacuo. The residue was recrystallized from 240 mL ethanol under heating. The suspension was stored for 1 h at -18C. The trityl protected product 33 was filtered off, washed 2x with ethanol and dried under high vacuum. Yield: 19.6 g; 90 %MS: m/z = 528.07 [M+Na]+

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; ASCENDIS PHARMA A/S; BISEK, Nicola; RAU, Harald; CLEEMANN, Felix; KNAPPE, Thomas; REIMANN, Romy; (140 pag.)WO2016/20373; (2016); A1;,
Indoline – Wikipedia,
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