Category: indolines-derivatives

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., Quality Control of 5-Methoxyindolin-2-one

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 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:
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;,
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Adding a certain compound to certain chemical reactions, such as: 61-70-1, name is 1-Methylindolin-2-one, 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 61-70-1, Formula: C9H9NO

General procedure: An oven-dried reflux tube equipped with a magnetic stir bar and a Teflon stopcock was charged with aryl halide (1 mmol), oxindole (1 mmol),potassium carbonate (1.1 mmol), catalyst nanoparticles (0.05 mmol)and 1,4-dioxane (2 ml) and heated at 70 C. The mixture was vigorously stirred under these reaction conditions and completion of the reaction was monitored by TLC (EtOAc: n-hexane, 25:75). After completion of the reaction, the reaction mixture was cooled to room temperature, the magnetic nanoparticles of the catalyst were collected using a magnet. Ethyl acetate (5 mL) and water (10 mL)were added to the mixture in the next step. The aqueous layer was furtherextracted by ethyl acetate (2*5 mL). The combined organic layerswere washed with saturated brine, dried over CaCl2, filtered, and concentrated to give a residue which was purified by recrystallization from ethanol and water or by column chromatography on silica gelusing EtOAc: n-hexane, 1:7.

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

Reference:
Article; Moghaddam, Firouz Matloubi; Tavakoli, Ghazal; Latifi, Fatemeh; Saeednia, Borna; Catalysis Communications; vol. 75; (2016); p. 37 – 41;,
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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. 110568-64-4, name is 6-Nitroisoindolin-1-one, A new synthetic method of this compound is introduced below., Recommanded Product: 110568-64-4

Synthesis of tert-butyl 5-nitro-1-oxoisoindoline-2-carboxylate (2) To a stirred solution of 5-nitroisoindolin-1-one (1, 0.4 g, 2.24 mmol) in acetonitrile (20 mL), N,N-dimethylaminopyridine (0.41 g, 3.37 mmol) followed by di-tert-butyl dicarbonate (0.75 mL, 3.37 mmol) were added. The reaction mixture was allowed to stir at room temperature for 12 h. The reaction mixture was quenched with water and extracted with ethyl acetate. The organic layer was washed with brine, separated, dried over sodium sulphate and concentrated under reduced pressure. The crude was purified by silica gel column chromatography using 25% ethyl acetate in hexane to afford tert-butyl 5-nitro-1-oxoisoindoline-2-carboxylate (2). Yield: 0.36 g, 57%; MS (ESI) m/z 279 [M+1]+.

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; eFFECTOR Therapeutics, Inc.; Sprengeler, Paul A.; Reich, Siegfried H.; Ernst, Justin T.; Webber, Stephen E.; Shaghafi, Mike; Murphy, Douglas; Tran, Chinh; (131 pag.)US10112955; (2018); B2;,
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Some common heterocyclic compound, 40314-06-5, name is 5-Methylisoindoline-1,3-dione, molecular formula is C9H7NO2, 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. Recommanded Product: 5-Methylisoindoline-1,3-dione

N-4-methylphenylglycine ethyl ester (0.3 mmol) under air atmosphere,A phthalimide compound (0.2 mmol) and cuprous chloride (0.02 mmol) were placed in a dry reaction tube with stirring magnets.Then into the test tubeAn acetonitrile solvent (2 mL) was added and the reaction tube was reacted in an air atmosphere at 60 C for 24 hours.After the reaction was completed, it was cooled to room temperature, and the solvent was distilled off under reduced pressure using a rotary evaporator.The residue was purified by column chromatography to give a pure pale yellow solid 3 mThe yield was 65%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 40314-06-5, its application will become more common.

Reference:
Patent; Donghua University Of Science And Technology; Zhu Zhiqiang; Xiao Lijin; Xie Zongbo; Yue Changgao; (12 pag.)CN108623514; (2018); A;,
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Electric Literature of 1168150-46-6, 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. 1168150-46-6, name is (E)-Methyl 3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of intermediate (3a, 3b, 6a, 6b, 10a, 10b, 11a-d, and14a-g, 1.5 mmol) and methyl (E)-3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate (1.5 mmol) in methanol (10 mL) wasstirred under reflux for 5-10 h. When TLC showed the completionof the reaction, the solution was cooled to room temperature. Theprecipitate was filtered off to give a crude product, which wasrecrystallized from methanol to provide the target compounds.

The synthetic route of (E)-Methyl 3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Qin, Mingze; Tian, Ye; Sun, Xiaoqing; Yu, Simiao; Xia, Juanjuan; Gong, Ping; Zhang, Haotian; Zhao, Yanfang; European Journal of Medicinal Chemistry; vol. 139; (2017); p. 492 – 502;,
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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. 675109-26-9, name is 6-Bromoisoindolin-1-one, A new synthetic method of this compound is introduced below., COA of Formula: C8H6BrNO

(4) The compound obtained in step (3) (80 g, 0.38 mol) was dissolved in 1 L of dichloromethane.A 1 N solution of borane tetrahydrofuran (1 L) was added dropwise and stirred at room temperature for 4 hours.Then heated to reflux for 3 hours. The system cooled down,100 ml of 2N hydrochloric acid was added dropwise and the mixture was stirred at room temperature for 3 hours and then refluxed for 4 hours. Cooling filtration,The cake was washed with dichloromethane to give an off-white powder that was the target.

The synthetic route of 675109-26-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Xinyuan Pharmaceutical Technology Co., Ltd.; Wu Tianjun; (9 pag.)CN107474006; (2017); A;,
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Reference of 60434-13-1, The chemical industry reduces the impact on the environment during synthesis 60434-13-1, name is 5-Chloro-1-methylindoline-2,3-dione, I believe this compound will play a more active role in future production and life.

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.

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-Chloro-1-methylindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

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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Synthetic Route of 446292-08-6, 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. 446292-08-6, name is (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

42.2g was added to the reaction flask2-[[(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-5-oxazolidinyl]methyl]-1H-isoindole -1,3(2H)-dione,8.6 g of 40% aqueous solution of methylamine and 200 g of absolute ethanol; the temperature was raised to 60 C by stirring, the reaction was kept for 3 hours, the system was cooled to 25 C, 2.8 g of DMTMM was added as a condensing agent, and 17.8 g of 5-chlorothiophene-2-carboxylic acid was dissolved. 35.6g of anhydrous ethanol was added to the system, and the reaction was completed at 25 C for 12 hours. The reaction was completed, and a white solid was obtained by filtration. The mixture was washed with 100 g of anhydrous ethanol and a mixture of water and a mass ratio of 1:1, and filtered to obtain a white solid. Drying at a temperature of 55 C, pressure ? 0.08 MPa for 8 h under reduced pressure, 40.5 g of rivaroxaban dry product (yield: 92.8%; HPLC chiral purity:99.9%),

The synthetic route of (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu Zhongbang Pharmaceutical Co., Ltd.; Wu Siqing; Jiang Haisong; Wang Hongxi; Xu Pengfei; Huang Shuang; (7 pag.)CN108250193; (2018); A;,
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Electric Literature of 2058-74-4, 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 2058-74-4 as follows.

General procedure: To a solution of L-proline-melamine complex (3 mol%) in DMSO (2 mL) was added dimedone 0.025 mg (0.178 mmol), malononitrile (1 equiv) and benzaldehyde / isatin (1 equiv) and stirred at room temperature for 1-20 min. After completion of the reaction (monitored by TLC), ethyl acetate was added stirring and continued for another 5 min. The precipitate formed was filtered. Evaporation of solvent gave the crude product which was recrystallized using ethanol to give the pure compound.

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:
Article; Nagaraju, Sakkani; Paplal, Banoth; Sathish, Kota; Giri, Santanab; Kashinath, Dhurke; Tetrahedron Letters; vol. 58; 44; (2017); p. 4200 – 4204;,
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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. 6326-79-0, name is 6-Bromoisatin belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Product Details of 6326-79-0

For example, Compound 3 (N-benzyl-6-bromoindoline-2,3-dione) was prepared according to Scheme 1a: 6-Bromoisatin (SM1) (984 mg, 4.35 mmol, 1.0 equiv) was dissolved in N,N-dimethylformamide (8.70 mL), and the orange solution was cooled to 0 C. Sodium hydride (183 mg, 4.57 mmol, 60% dispersion in mineral oil, 1.05 equiv) was added in two portions, and the resulting purple suspension was maintained at 0 C. for 15 min. Benzyl bromide (604 muL, 5.05 mmol, 1.16 mmol) was added dropwise, and the resultant orange solution was maintained at 0 C. for 30 min. Water (30 mL) was added, and the biphasic mixture was extracted with EtOAc (4¡Á50 mL). The combined organics were dried over Na2SO4 and concentrated. Purification of the residue by silica gel flash column chromatography (gradient 1:3 EtOAc-hexanes to 100% EtOAc) gave Compound 3 (1.31 g, 95%) as an orange solid: mp 190192 C.; Rf 0.69 (3:7 EtOAc-hexanes); 1H NMR (500 MHz, CDCl3): delta 7.47 (d, J=7.9 Hz, 1H), 7.417.36 (m, 2H), 7.367.31 (m, 3H), 7.287.24 (m, 1H), 6.96 (d, J=1.4, 1H), 4.91 (s, 2H); 13C NMR (125 MHz, CDCl3): delta 182.1 (C), 158.3 (C), 151.6 (C), 134.2 (C), 133.7 (C), 129.4 (CH), 128.6 (CH), 127.6 (CH), 127.3 (CH), 126.5 (CH), 116.5 (C), 114.7 (CH), 44.4 (CH2); IR (film): 1733, 1603 cm1; HRMS-ESI (m/z) [M+Na]+ calcd. for C15H10NO2BrNa, 337.9792; found, 337.9786.

The synthetic route of 6326-79-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Horne, David A.; Jove, Richard; Lincoln, Christopher; Nam, Sangkil; Overman, Larry; Xie, Jun; US2013/225637; (2013); A1;,
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