Category: indolines-derivatives

496-12-8, name is Isoindoline, 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. SDS of cas: 496-12-8

To a suspension of 2-[4-(2-bromoethoxy)-3,5-dimethylphenyl]-5,7-dimethoxy-3H-quinazolin-4-one (0.50 g, 1.15 mmol) in anhydrous DMF (9 mL) was added isoindoline (0.41 mL, 3.46 mmol) and the reaction mixture was stirred at room temperature for 16 hours under nitrogen. The solvent was removed under reduced pressure and the residue was triturated with water (50 mL). The separated solid was filtered, washed with water and ether, and dried under vacuum to give the title compound as a white solid. Yield: 0.45 g (83%). MP 202-202.5 C. 1H NMR (400 MHz, CDCl3): delta 10.09 (br s, 1H), 7.77 (s, 2H), 7.22 (br s, 4H), 6.83 (d, J=2.4 Hz, 1H), 6.46 (d, J=2.4 Hz, 1H), 4.11 (s, 4H), 4.03 (t, J=6.0 Hz, 2H), 3.96 (s, 3H), 3.93 (s, 3H), 3.22 (t, J=6.0 Hz, 2H), 2.42 (s, 6H)

The synthetic route of 496-12-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RVX Therapeutics Inc.; McLure, Kevin G.; Young, Peter R.; US2013/281399; (2013); A1;,
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Synthetic Route of 7699-18-5,Some common heterocyclic compound, 7699-18-5, name is 5-Methoxyindolin-2-one, molecular formula is C9H9NO2, 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 Schlenk tube were added oxindole 1 (0.3 mmol), t-BuONO (0.6 mmol), andTHF (2 mL). Then the tube was stirred at 50 C under 1 atm of O2 for the indicatedtime until complete consumption of starting material monitored by TLC analysis.After the reaction was finished, the reaction mixture was washed with brine. The aqueous phase was re-extracted with ethyl acetate. The combined organic extractswere dried over Na2SO4, removal of the solvent under vacuum afforded the crudeproduct, which was purified further by column chromatography using hexane-ethylacetate.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Methoxyindolin-2-one, its application will become more common.

Reference:
Article; Wei, Wen-Ting; Ying, Wei-Wei; Zhu, Wen-Ming; Wu, Yi; Huang, Yi-Ling; Cao, Yi-Qi; Wang, Yi-Ning; Liang, Hongze; Synlett; vol. 28; 17; (2017); p. 2307 – 2310;,
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Electric Literature of 4702-13-0,Some common heterocyclic compound, 4702-13-0, name is N-Phthaloylglycine, molecular formula is C10H7NO4, 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.

In the (G2a) step, 2 mol of thionylchloride (SOCl2) was added to the compound 1a to produce 2-(1,3-dioxoisoindolin-2-yl)acetic chloride (compound 2a) and the unreacted thionylchloride (SOCl2) was recovered by using an aspirator.

The synthetic route of 4702-13-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THERMOLON KOREA CO.,LTD.; WO2009/131324; (2009); A2;,
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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. 774-47-0, name is 5,6-Difluoroindoline-2,3-dione, A new synthetic method of this compound is introduced below., Application In Synthesis of 5,6-Difluoroindoline-2,3-dione

The 5,6-difluoro isatin(1.83g, 10mmol)Add 10 mL of acetonitrile to a 100 mL round bottom flask.N-methylpiperazine (1.10 g, 11 mmol) was added dropwise, followed by stirring at room temperature for 4 h. After the reaction was monitored by TLC, purification by column chromatography gave a red solid with a yield of 48%.

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; Sun Yat-sen University; Huang Zhishu; Tan Jiaheng; Che Tong; (27 pag.)CN107540662; (2018); A;,
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Electric Literature of 825-70-7, 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 825-70-7 as follows.

General procedure: to a suspension of iv (1mmol) in acetonitrile (10ml) was added 5-fluoroindoline (1.2mmol). The reaction mixture was stirred at 40C for 16h and then evaporated to dryness under reduced pressure. Water (10mL) and diethylether (15mL) were added and the resulting mixture was stirred for 5min. The precipitate formed was filtered off and dried to give 7 (86%) as a white solid.

According to the analysis of related databases, 825-70-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Certal, Victor; Halley, Frank; Virone-Oddos, Angela; Filoche-Romme, Bruno; Carry, Jean-Christophe; Gruss-Leleu, Florence; Bertin, Luc; Guizani, Houlfa; Pilorge, Fabienne; Richepin, Patrick; Karlsson, Andreas; Charrier, Veronique; Abecassis, Pierre-Yves; Vincent, Loic; Nicolas, Jean-Paul; Lengauer, Christoph; Garcia-Echeverria, Carlos; Schio, Laurent; Bioorganic and Medicinal Chemistry Letters; vol. 24; 6; (2014); p. 1506 – 1510;,
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Synthetic Route of 3484-35-3, 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. 3484-35-3, name is 5-Methylindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 22 3- [2,4-Dimethyl-5-(5-methyl-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-1H-pyrrol-3-yl]-propionic acid 3-(2-Carboxyethyl)-2,4-dimethyl-5-formylpyrrole (97.5 mg), 74 mg 5-methyl-2-oxindole, and 75 muL piperidine in 3 mL of ethanol were heated at 95 C. for 5 hours. The reaction mixture was cooled and concentrated. The residue was suspended in 6 N aqueous hydrochloric acid. The precipitate was filtered, washed with water to pH 6 and dried in a vacuum oven overnight to give 104 mg (64%) of the title compound as a yellow solid. 1H-NMR (360 MHz, DMSO-d6): delta 13.38 (s, br, 1H, NH-1′), 12.02 (s, br, 1H, COOH), 10.57 (s, br, 1H, NH-1), 7.52 (s, br, 1H, H-4), 7.50 (s, 1H, H-vinyl), 6.87 (d, J=7.86 Hz, 1H, H-6), 6.73 (d, J=7.86 Hz, 1H, H-7), 2.63 (t, J=7.49 Hz, 2H, CH2CH2COOH), 2.34 (t, J=7.49 Hz, 2H, CH2CH2COOH), 2.29 (s, 3H, CH3), 2.28 (s, 3H, CH3), and 2.24 (s, 3H, CH3); MS m/z (relative intensity, %) 325 ([M+1]+, 66).

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, 5-Methylindolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sugen, Inc.; US6395734; (2002); B1;,
Indoline – Wikipedia,
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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. 65826-95-1, name is 5-Methylindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. category: indolines-derivatives

(1) 1.33 g of 5-methylindoline and 2-chloropyridine were added to a 50 mL round bottom flask, the ratio of the amount of the substance was 1: 1.5; (2) Stir directly in the air and mix evenly at room temperature.Then heated at 80 C, after 45 min, the system solidified, stopped the reaction, and cooled to room temperature; (3) Add 50 mL of saturated NaHCO3 solution to the system to dissolve the solid.Further, 50 mL of ethyl acetate solution was added, shaken, and liquid-separated, and the aqueous phase was extracted three times with ethyl acetate, 30 mL each time, and the organic phase was combined and concentrated by a rotary evaporator; (4) The concentrate was dissolved in 20 mL of ethanol, refluxed at 80 C for 15 min, cooled, and a pale yellow solid was separated, filtered, rinsed with water and dried in vacuo to give the desired product.

The synthetic route of 65826-95-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Northwest University; Jiao Linyu; Zhang Ze; Yin Xiaomei; Hong Qian; Ning Zihui; Ma Xiaoxun; Li Zhuo; Sun Ming; (11 pag.)CN109265439; (2019); A;,
Indoline – Wikipedia,
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Reference of 667463-64-1, A common heterocyclic compound, 667463-64-1, name is 6-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.

I-5.1 (15.0 g, 63 mmol) and hydrazine hydrate (30 mL, 618 mmol) are heated to 125 C. for 72 h. To the cool reaction mixture DCM is added and extracted with water and 1 M HCl. The organic layer is dried over MgSO4 and concentrated. The crystallized residue is dissolved in DCM, methanol is added and the DCM is removed under vacuum. The crystallized product is filtered with sunction and washed with cold methanol. Yield 63%, m/z 226/228 [M+H]+, rt 1.16 min, LC-MS Method V001-003

The synthetic route of 667463-64-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ANDERSKEWITZ, Ralf; GRAUERT, Matthias; GRUNDL, Marc; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; US2014/275159; (2014); 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. 19155-24-9, name is 3,3-Dimethylindolin-2-one, A new synthetic method of this compound is introduced below., Quality Control of 3,3-Dimethylindolin-2-one

To a mixture of 3,3-dimethyloxindole (409 mg, 2.53 mmol), (S)-3-chloro-1-phenyl-1-propanol (376 mg, 2.20 mmol) and triphenylphosphine (664 mg, 2.53 mmol) in tetrahydrofuran (5 mL) under nitrogen was added slowly diisopropyl azodicarboxylate (490 muL, 2.53 mmol) via a syringe. The resulting solution was stirred at room temperature overnight. Solvent was removed under reduced pressure and the viscous brown liquid residue was purified using Isco CombiFlash Companion chromatography (RediSep 12-g silica column, 0-12percent ethyl acetate/hexane) to give 236 mg (34percent) of 1-[(1R)-3-chloro-1-phenylpropyl]-3,3-dimethyl-1,3-dihydro-2H-indol-2-one as a viscous colorless liquid. MS (ES) m/z 314.1 ([M+H]+); HRMS: calculated for C19H20ClNO+H+, 314.1306; found (ESI, [M+H]+), 314.1299.

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; Wyeth; US2007/72928; (2007); A1;,
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. 7699-18-5, name is 5-Methoxyindolin-2-one, A new synthetic method of this compound is introduced below., HPLC of Formula: C9H9NO2

General procedure: To the 3-subtitutedphenyl-1H-pyrazole-5-carbaldehydes 11(a-d) prepared in the above step was added corresponding substituted oxindoles and catalytic amount of piperdine (1.0ml) in ethanol. Heated the reaction mixture to reflux for 4h at 85C. The solid compounds obtained in the reaction vessel were filtered and washed with ethanol for 4-5 times. After complete air drying the final compounds (Z)-3-((3-phenyl-1H-pyrazol-5-yl)methylene)indolin-2-one analogs 12(a-u) were obtained as pure solids (yield 75-80%).

The synthetic route of 7699-18-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kamal, Ahmed; Shaik, Anver Basha; Jain, Nishant; Kishor, Chandan; Nagabhushana, Ananthamurthy; Supriya, Bhukya; Bharath Kumar; Chourasiya, Sumit S.; Suresh, Yerramsetty; Mishra, Rakesh K.; Addlagatta, Anthony; European Journal of Medicinal Chemistry; vol. 92; (2015); p. 501 – 513;,
Indoline – Wikipedia,
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