Category: indolines-derivatives

Some common heterocyclic compound, 132898-96-5, name is 2,3-Dioxoindoline-5-sulfonyl chloride, molecular formula is C8H4ClNO4S, 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. Safety of 2,3-Dioxoindoline-5-sulfonyl chloride

A solution of rpml21 (0.211 g, 0.861 mmol) and morpholine (0.187 g, 2.139 mmol, 2.5 eq), in anhydrous DCM (7 ml) and anhydrous chloroform (1 ml) was stirred for 3h at room temperature under Ar. The yellow precipitate was collected by filtration and dried under vacuum. The crude product was used in the next step without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 132898-96-5, its application will become more common.

Reference:
Patent; UNIVERSITY OF SOUTH FLORIDA; H. LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE, INC.; WO2007/117699; (2007); A2;,
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Related Products of 611-09-6, These common heterocyclic compound, 611-09-6, name is 5-Nitroindoline-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: 30 mg of SiO2_g-C3N4 nanocomposite was dispersed in aqueous media (3 ml) for 30 min and dimedone or 4-hydroxycoumarin (1 mmol), malononitrile (1 mmol) and isatin (1.0 mmol) were added to the mixture. Then, the mixture was stirred at reflux conditions for an appropriate time, while the reaction progress was monitored by thin layer chromatography (TLC). After the reaction was completed, ethyl acetate was employed for the extraction of crude product and the products were dried over anhydrous Na2SO4. The solvent was evaporated followed by recrystallizing of the crude product in hot ethanol, and pure products were identified by IR, 1H and 13C NMR spectral data. The SiO2_g-C3N4 nanocatalyst was washed with EtOH, dried and reused for the next run.

Statistics shows that 5-Nitroindoline-2,3-dione is playing an increasingly important role. we look forward to future research findings about 611-09-6.

Reference:
Article; Allahresani, Ali; Taheri, Bahare; Nasseri, Mohammad Ali; Research on Chemical Intermediates; vol. 44; 2; (2018); p. 1173 – 1188;,
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Application of 320734-35-8,Some common heterocyclic compound, 320734-35-8, name is 7-Bromooxindole, 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.

General procedure: A mixture of 2a-j (1.50 mmol) and 5 (1.50 mmol) in ethanol (10 mL) was treated with a catalytic amount of piperidine. The reaction mixture was stirred under reflux until complete consumption of the substituted indolin-2-ones was observed by TLC. After cooling, the precipitate was filtered, recrystallised from absolute ethanol and dried in air to furnish pure (E)-3-(benzothiazol-2-ylmethylene)indolin-2-ones 6a-j.

The synthetic route of 320734-35-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Chao; Xu, Juan; Zhao, Xinyu; Kang, Congmin; Journal of Chemical Research; vol. 41; 9; (2017); p. 537 – 540;,
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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. Product Details of 19727-83-4

10.0 g (0.061 mol) of 6-nitro-2,3-dihydro-1H-indole (16) was dispersed in 100 ml of dimethylformamide in a synthetic nitrogen atmosphere, stirred for about 10 minutes at room temperature,12.6 g (0.068 mol) of (1-bromoethyl) benzene and 12.4 ml (0.073 mol) of diisopropylethylamine (DIPEA) were added to the reaction solution. The reaction solution was gradually heated and stirred at 100 C for 5 hours, Completed.After cooling the reaction mixture to room temperature, 100 ml of distilled water and 200 ml of ethyl acetate were added and the mixture was stirred for 30 minutes. The organic layer was separated and washed with H 2 O. The recovered organic layer was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure The obtained solid product was dispersed in 50 ml of methanol, stirred for 30 minutes, filtered and dried to obtain 12.5 g of 6-nitro-2,3-dihydro-1- (1-phenylethyl)-1H-indole (76.7%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 19727-83-4, its application will become more common.

Reference:
Patent; Korea Research Institute of Chemical Technology; Shin Seung-rim; Jeon Geun; Shin Jong-il; Park Yeong-il; Ahn Gyeong-ryong; (48 pag.)KR101842495; (2018); B1;,
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19155-24-9, name is 3,3-Dimethylindolin-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. Safety of 3,3-Dimethylindolin-2-one

A solution of 3,3-dimethylindolin-2-one (1.5 g, 9.31 mmol)Was dissolved in tetrahydrofuran (90 mL)The solution was cooled to 0 ° C,To this was added borane-tetrahydrofuran (37.3 mL, 37.22 mmol).The reaction solution was refluxed at 87 ° C overnight,Cooled to room temperature and quenched with methanol (10 mL).The mixture was further refluxed at 85 ° C for 2 hours, after which it was concentrated under reduced pressure.The residue was purified by silica gel column chromatography (petroleum ether / ethyl acetate (v / v) = 20/1)The title compound was obtained as a yellow oil (0.87 g, 63.5percent).

The synthetic route of 19155-24-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jiatuo Sciences Corporation; Xi Ning; Wang Ruyong; Wang Liang; (112 pag.)CN104016979; (2017); B;,
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Electric Literature of 15362-40-0, 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. 15362-40-0, name is 1-(2,6-Dichlorophenyl)-2-indolinone belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 9 1-(2,6-Dichlorophenyl)-3-isopropylidene-1,3-di-hydro-2H-indol-2-one 1-(2,6-Dichlorophenyl)-oxindole (27.8 g; 0.10 mole) is dissolved in 300 ml of acetone, pyrrolidine (10 ml; 0.12 mole) is measured to the solution and it is warmed to reflux temperature. The reaction mixture is refluxed for 3 hours and the solution is evaporated. The product separated in crystalline form is dissolved in dichloro-methane, extracted twice with 10% hydrogen chloride, the organic phase is dried over sodium sulfate, clarified with bone coal, filtered and evaporated. The product is used for the catalytic hydrogenation without recrystallization. Analytical samples may be obtained by recrystal-lization from ethyl acetate. Yield: 31.82 g of yellow crystal (97%). M.p.: 180-182 C. (ethyl acetate). IR (KBr): 1700 (C=O), 793 cm-1. 1H-NMR (CDCl3, TMS, 400 MHz): 2.46 (3H, s), 2.66 (3H, s), 6.40 (1H, dd, J=0.6, 7.8 Hz), 7.09 (1H, dt, J=1.2, 7.6 Hz), 7.17 (1H, dt, J=1.0, 7.6 Hz), 7.35 (1H, dd, J=7.6, 8.7 Hz), 7.50 (2H, d, J=8.2 Hz), 7.64 (1H, d, J=7.5 Hz) ppm. 13C-NMR (CDCl3, TMS, 101 MHz): 23.4, 25.4, 108.5, 122.0, 122.3, 123.7, 123.8, 127.6, 128.9, 130.4, 130.9, 135.9, 140.0, 156.1, 166.2 ppm. Analysis for the Formula C17H13Cl2NO (318.21): Calculated: C, 64.17; H, 4.12; Cl, 22.28; N, 4.40%. Found: C, 64.02; H, 4.11; Cl, 22.14; N, 4.39%.

The synthetic route of 1-(2,6-Dichlorophenyl)-2-indolinone has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EGIS GYOGYSZERGYAR RT.; US2007/232619; (2007); 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 199328-10-4 as follows. Recommanded Product: 199328-10-4

EXAMPLE I Methyl 1-acetyl-2-indolinone-5-carboxylate 10.5 g of methyl 2-indolinone-5-carboxylate (prepared analogously to Ogawa, Hidenori et al. in Chem.Pharm.Bull 36, 2253-2258 (1988)) are stirred in 30 ml of acetic anhydride for 4 hours at 140 C. The mixture is then left to cool, poured onto ice water and the precipitate is suction filtered. The product is washed with water once more, then taken up in methylene chloride, dried over sodium sulphate and concentrated by evaporation. Yield: 11 g (86% of theory), Rf value: 0.63 (silica gel, methylene chloride/methanol=50:1).

According to the analysis of related databases, 199328-10-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Boehringer Ingelheim Pharma KG; US6319918; (2001); B1;,
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Synthetic Route of 1074-82-4, These common heterocyclic compound, 1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide, 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 phthalimide10(6.8 mmol) dissolved in EtOH (20 mL) was gently boiled for about 1h. The hot solution was decanted from any solid into 1.25 mL of a specially prepared solution of KOH (15.25 g KOH dissolved in 15 mL of H2O and 45 mL of EtOH). A precipitate of potassium phthalimide separates at once. The mixture was stirred and cooled quickly to room temperature, and the precipitate was filtered under vacuum. To the alcoholic mother liquors a second 1 g portion of phthalimide was added, and the entire process was repeated. The two crops of crystals were united and washed with acetone to remove any unchanged phthalimide. After air-dried pure potassium phthalimidewas obtained as white crystals (yield 30%). In a second step, a mixture of potassium phthalimide (2.2 mmol),the appropriate dibromoalkane derivative (2.9 mmol) and 2.5 mL of acetone was stirred and refluxed for 24h, and then cooled to 15 C. After filtering off the precipitated potassium bromide, the cake was washed with acetone and the solvent evaporated to give pure compound.

The synthetic route of 1074-82-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Capela, Rita; Magalhaes, Joana; Miranda, Daniela; Machado, Marta; Sanches-Vaz, Margarida; Albuquerque, Ines S.; Sharma, Moni; Gut, Jiri; Rosenthal, Philip J.; Frade, Raquel; Perry, Maria J.; Moreira, Rui; Prudencio, Miguel; Lopes, Francisca; European Journal of Medicinal Chemistry; vol. 149; (2018); p. 69 – 78;,
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Reference of 2058-72-2, A common heterocyclic compound, 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, molecular formula is C9H6BrNO2, 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 solution of chromones 1 (0.2 mmol), isatins 2 (0.3 mmol) and proline, or thioproline (0.5 mmol) in the 4.0 mL of EtOH at 80 C in oil bath for 3 h. After completion of the reaction, as indicated by TLC, the reaction solvent was directly removed, and purification by flash column chromatography (petroleum ether/EtOAc = 5:1~10:1) was carried out to furnish the corresponding products 3.

The synthetic route of 2058-72-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yue, Jing; Chen, Shuang; Zuo, Xiong; Liu, Xiong-Li; Xu, Sheng-Wen; Zhou, Ying; Tetrahedron Letters; vol. 60; 2; (2019); p. 137 – 141;,
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Application of 959235-95-1, The chemical industry reduces the impact on the environment during synthesis 959235-95-1, name is 6-(Trifluoromethoxy)indoline, I believe this compound will play a more active role in future production and life.

A mixture of 6-(trifluoromethoxy)indoline [CAS 959235-95-1] (577 mg, 2.84 mmol),2-(2-(4-(tert-butoxy)-4-oxobutoxy)-4-ch lorophenyl )-2-((3-methoxy-5-(methylsulfonyl)phenyl)amino)acetic acid 7d (1 .5 g, 2.84 mmol), HATU (1 .62 g, 4.26 mmol) and diisopropylethylamine (1 .4 mL, 8.5 mmol) in DMF (60 mL) was stirred at room temperature for 12 h. The mixture was diluted with water. The precipitate was filtered off and washed with water. The precipitate was taken upwith EtOAc, washed with an aqueous solution of K2003 10%, water, dried over MgSO4, filtered and the solvent was concentrated under reduced pressure. Purification was performed by flash chromatography on silica gel (15-40 pm, 120 g, heptane/EtOAc 60/40) to give, after crystallization from petroleum ether/diisopropyl ether, tert-butyl 4-(5-chloro-2-(1 -((3-methoxy-5-(methylsulfonyl)phenyl)amino)-2-oxo-2-(6-(trifluoromethoxy)indolin-1 -yl)ethyl)phenoxy)butanoate 9a (1 .02 g).

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-(Trifluoromethoxy)indoline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JANSSEN PHARMACEUTICALS, INC.; KATHOLIEKE UNIVERSITEIT LEUVEN; BARDIOT, Dorothee Alice Marie-Eve; KESTELEYN, Bart Rudolf Romanie; BONFANTI, Jean-Francois; RABOISSON, Pierre Jean-Marie Bernard; MARCHAND, Arnaud Didier M; (64 pag.)WO2018/178238; (2018); A1;,
Indoline – Wikipedia,
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