Category: indolines-derivatives

2436-29-5, name is 3-(1,3-Dioxoisoindolin-2-yl)propanal, 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. Computed Properties of C11H9NO3

To a solution of 1-(1-benzyl-5-chloro-1H-indole-2-yl)-2-methylpropan-1-amine (0.44 mmol) in 10 mL of anhydrous DCM, was added aldehyde (0.44 mmol) and sodium triacetoxyborohydride (0.44 mmol) at 0 C. The mixture was stirred at room temperature overnight. The solution was poured into 10% aq. NaOH, and extracted with EtOAc (¡Á3). The organic layers were combined, washed with H2O (¡Á3), brine (¡Á3), dried (Na2SO4), filtered, and the filtrate was concentrated. The material was purified by flash chromatography (20% EtOAc:hexane) to yield 40 mg of title compound

The synthetic route of 2436-29-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boyce, Rustum S.; Guo, Hongyan; Mendenhall, Kris G.; Walter, Annette O.; Wang, Weibo; Xia, Yia; US2006/84687; (2006); 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. 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, A new synthetic method of this compound is introduced below., Recommanded Product: 2058-72-2

General procedure: Isatin (1 mmol), dimedone (280 mg, 2 mmol) and ZnO (0.25 mmol) were taken in the round bottom flask and heated to 100 C for 2 h. The progress of the reaction was monitored by TLC. After completion, the reaction mixture was suspended in 6 mL (3:3 v/v) chloroform and methanol mixture and the catalyst was filtered through Whatman filter paper. The filtrate was concentrated under reduced pressure and the residue was purified by recrystallization in ethanol solvent. The recovered catalyst dried and used for next cycle.

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; Kothandapani, Jagatheeswaran; Ganesan, Asaithampi; Mani, Ganesh Kumar; Kulandaisamy, Arockia Jayalatha; Rayappan, John Bosco Balaguru; Selva Ganesan, Subramaniapillai; Tetrahedron Letters; vol. 57; 31; (2016); p. 3472 – 3475;,
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317-20-4, name is 7-Fluoroisatin, 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. name: 7-Fluoroisatin

General procedure: In a 25 mL round bottom flask, isatins 1 (1 mmol), 3-phenylisoxazol-5(4H)-one 2 (1 mmol) or 3-ethylisoxazol-5(4H)-one 7 (1 mmol), pyrazol-5-amine 3 (1 mmol) or 6-aminopyrimidine-2,4-(1H,3H)-dione 5 (1 mmol), and Amberlyst-15 (100 mg) were stirred in CH3OH (5.0 mL) at 80 C. When the reaction was completed (detected by TLC), the spherical catalyst was separated by a sieve at once under hot condition. Then, the reaction mixture was cooled to room temperature, and solid precipitation occurred. After filtration, the crude product was recrystallized from EtOH and DMF to give pure compound.

The synthetic route of 317-20-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Niu, Qingqing; Xi, Junhua; Li, Lei; Li, Li; Pan, Chengli; Lan, Meijun; Rong, Liangce; Tetrahedron Letters; vol. 60; 43; (2019);,
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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. 61-70-1, name is 1-Methylindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., name: 1-Methylindolin-2-one

General procedure: All reactions were conducted in 10 mL glass vials fitted with crimpcap septum caps. The reaction vial, equipped with a magnetic stir bar,was charged under an N2 atmosphere with 1-methylindolin-2-one (4)(73.6 mg, 0.5 mmol), Pd2(dba)3 (10 mg, 0.011 mmol, 2.5 mol%), i-Pr-BI-DIME (7) (0.022 mmol, 5 mol%), LiHMDS (1 M in toluene, 0.55 mL,0.55 mmol) and the aryl halide (1.1 equiv), then sealed with a crimpcap septum. THF (0.5 mL) and toluene (0.5 mL) were added via syringe and the reaction was heated to 70 C for 4-24 h. The reaction mixture was cooled to room temperature then filtered through a Celite pad with EtOAc (5 mL) as eluent. The filtered solution waswashed with H2O (3 mL), dried over MgSO4 and then concentrated under reduced pressure. The crude residue was purified using a 12 g silica column (30% EtOAc/hexanes) to afford the corresponding oxindole product.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 61-70-1.

Reference:
Article; Mangunuru, Hari P. R.; Malapit, Christian A.; Haddad, Nizar; Reeves, Jonathan T.; Qu, Bo; Rodriguez, Sonia; Lee, Heewon; Yee, Nathan K.; Song, Jinhua J.; Busacca, Carl A.; Senanayake, Chris H.; Synthesis; vol. 50; 22; (2018); p. 4435 – 4443;,
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Reference of 13861-75-1, 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. 13861-75-1, name is Spiro[cyclopropane-1,3′-indolin]-2′-one, This compound has unique chemical properties. The synthetic route is as follows.

A dried flask under nitrogen was charged with sodium hydride (120 mg, 3.0 mmol) and DMF (1 mL). This rapidly stirred suspension was cooled to 0C using an ice/water bath and spiro[cyclopropane-l,3′-indolin]-2′-one (160 mg, 1.0 mmol, Preparatory Example 4) was added dropwise as a solution in DMF (2 mL). The ice/water bath was removed for 1 minutes before the mixture was recooled to 0C and 2-(chloromethyl)-l- isopentyl-lH-benzo[JJimidazole hydrochloride (236 mg, 1.0 mmol) was added dropwise as a solution in DMF (2.1 mL). The mixture was allowed to warm to rt and stirred there for 16 hours.The mixture was cooled to 0C and ice was added carefully. Partition between EtOAc and water was followed by separation, drying and concentration in vacuo. Preparative HPLC gave isolation of the desired compound, (1 10 mg, 0.31 mmol, 31%). ? NMR (400 MHz): ? 0.96 (d, 6H), 1.45 ( m, 2H), 1.60 (m, 2H), 1.69 (m, IH), 1.82(m, 2H), 4.26 (m, 2H), 5.35 (s, 2H), 6.83 (d, IH), 7.02 (dd, IH), 7.19 (dd, IH), 7.29 (m, 3H), 7.47 (d, IH), 7.81 (m, IH). LC/MS 360 (MH+).

The chemical industry reduces the impact on the environment during synthesis Spiro[cyclopropane-1,3′-indolin]-2′-one. I believe this compound will play a more active role in future production and life.

Reference:
Patent; RE:VIRAL LTD; COCKERILL, Stuart; PILKINGTON, Christopher; LUMLEY, James; ANGELL, Richard; MATHEWS, Neil; WO2013/68769; (2013); A1;,
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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. Application In Synthesis of Potassium 1,3-dioxoisoindolin-2-ide

o a stirred solution of 1,5-dibromopentane (13-k) (170.58 mL, 1.26 mol) in DMF (1.5 L) was added potassium phthalate (12-k) (78.0 g, 0.42 mol) portion-wise over 30 min at room temperature. After complete addition, the reaction mixture was stirred at 90C for 18 h, then quenched with water (3 L) and extracted with diethyl ether (500 mL x 4). The combined organic extracts were washed with water (500 mL x 2), followed by brine (500 mL x 2) and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain the crude. The residue was purified by silica gel column chromatography (60-120 mesh) using 5-10% EtOAc / hexanes to afford 14-k as an off-white solid (81 g, 65% yield).1H NMR (400 MHz, CDC13): delta 7.82 (dd, J= 5.5, 3.1 Hz, 2H), 7.69 (dd, J= 5.5, 3.0 Hz, 2H), 3.68 (t, J= 7.2 Hz, 2H), 3.38 (t, J= 6.8 Hz, 2H), 1.93-1.85 (m, 2H), 1.70 (p, J= 7.5 Hz, 2H), 1.53-1.43 (m, 2H).

The synthetic route of Potassium 1,3-dioxoisoindolin-2-ide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CV6 THERAPEUTICS (NI) LIMITED; SPYVEE, Mark; LADNER, Robert, D.; (244 pag.)WO2018/98208; (2018); A1;,
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Adding a certain compound to certain chemical reactions, such as: 110568-64-4, name is 6-Nitroisoindolin-1-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 110568-64-4, Formula: C8H6N2O3

A mixture of 5-nitro-1 lead noise isobutyl ketone Jie (100mg, 0.56mmoL), reduced iron powder (314mg, 5.6mmoL) was added to ethanol (2. OmL) and concentrated hydrochloric acid (0.5mL) and heated under reflux for 2 hours , TLC the reaction was complete. Cooling, the methanol solution saturated with ammonia (NH3) neutralizing the acid, diatomaceous earth filtration, washed with methanol, the solvent evaporated under reduced pressure to give a white solid 70.0mg, 84% yield

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; Shanghai Institute Of Materia Medica, Chinese Academy Of Sciences,; Duan, WenHu; Wan, huixin; Xia, GuangXin; Mei, deCheng; Lin, Yipeng; Liu, Xuejun; Shen, JingKang; (53 pag.)CN103804358; (2016); B;,
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Application of 2913-97-5, 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. 2913-97-5, name is N-(2-Oxoethyl)phthalimide belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a stirred solution of 2-(1, 3-dioxoisoindolin-2-yl) acetaldehyde (4.0 g, 21.15 mmol) in ethanol (40 mL) added hydroxylamine. HC1 (2.930 g, 42.305 mmol), followed by sodium bicarbonate (3.55 g, 42.305 mmol) at room temperature and stirred at roomtemperature for 16 h. Evaporated off the solvent, added water (50 mL) and extracted with ethyl acetate (2 x 100 mL). The combined organic layer was washed with water (100 mL), followed by brine , dried over sodium sulfate and concentrated under vaccue to give the titled compound (3.2 g, 74percent) as off white solid. LCMS: m/z 204.1 [M+H] ?H NMR (300 MHz, DMSO-d6) 11.36 (s, 1H), 7.98?7.78 (m, 4H), 6.83 (t, J= 3.8 Hz,1H), 4.39 (dd, J= 3.9, 0.9 Hz, 2H).

The synthetic route of N-(2-Oxoethyl)phthalimide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; CHIKKANNA, Dinesh; KHAIRNAR, Vinayak; PANIGRAHI, Sunil Kumar; WO2014/111871; (2014); A1;,
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Related Products of 2058-72-2, These common heterocyclic compound, 2058-72-2, name is 5-Bromo-1-methylindoline-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: To a stirred mixture of 1-benzyl-1H-indole-2,3-dione (1a, 0.25 g,1.05 mmol), CuI (0.01 g, 0.05 mmol, 0.05 equiv), and phenylacetylene (2a, 0.11 g, 1.11 mmol, 1.05 equiv) in anhyd toluene (2 mL), DBU (0.032 g, 0.21 mmol, 0.2 equiv) was added at 25 C under a N2 atmosphere. Stirring was continued at this temperature until the starting material was completely consumed (TLC monitoring). After completion, the mixture was quenched with sat. aq NH4Cl (2mL) and extracted with EtOAc (2 ¡Á 5 mL). The combined organic layers were dried (anhyd Na2SO4) and evaporated under reduced pressure to dryness. The crude product thus obtained was purified by column chromatography (activated silica gel, 60-120 mesh, hexane-EtOAc) to afford pure 3aa as a white solid; yield: 0.35 g (97%); mp 177-179 C.

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

Reference:
Article; Chouhan, Mangilal; Senwar, Kishna Ram; Kumar, Kapil; Sharma, Ratnesh; Nair, Vipin A.; Synthesis; vol. 46; 2; (2014); p. 195 – 202;,
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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. 201940-08-1, name is tert-Butyl 5-bromoisoindoline-2-carboxylate belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. category: indolines-derivatives

In a microwave vessel, a solution of 5-bromo-l,3-dihydro-isoindole-2-carboxylic acid tert- butyl ester (1.5 equiv.), di(pinacolato)diborane (2.0 equiv.), potassium acetate (2.0 equiv.) in 1,4-dioxane (2.0 mL) is flushed with nitrogen. [l,l’-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.05 equiv.) was then added and the reaction mixture was flushed again with argon (and heated up to 900C for 20 hours until the reaction is complete on TLC. No purification was carried out.

The synthetic route of 201940-08-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GALAPAGOS NV; MENET, Christel Jeanne Marie; JOUANNIGOT, Nolwenn; BLANC, Javier; VAN ROMPAEY, Luc Juliaan Corina; FLETCHER, Stephen Robert; WO2010/10186; (2010); A1;,
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