Indolines-derivatives

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. 32692-19-6, name is 5-Nitroindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C8H8N2O2

To a solution of 5-nitroindoline (11.72 g) and triethylamine (8.67 g) in N, N-dimethylformamide (150 ml) was added dropwise chloroacetyl chloride (8.06 g) at 5C and the mixture was stirred at ambient temperature for 20 hours. The mixture was poured into a mixture of ethyl acetate and water and the separated organic layer was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was triturated with ethyl acetate and collected by filtration to give 1- (CHLOROACETYL)-5-NITROINDOLINE (14.66 g) as a yellow crystal. 1H-NMR (DMSO-d6): 8 3. 28 (2H, t, J=8.6 Hz), 4.25 (2H, t, J=8.6 HZ), 4.64 (2H, s), 8.1-8. 2 (3H, m) ESI-MS (m/z): 263 (M+Na) +

The synthetic route of 32692-19-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FUJISAWA PHARMACEUTICAL CO., LTD.; DAISO CO., LTD.; WO2004/39795; (2004); A2;,
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Application of 6326-79-0, A common heterocyclic compound, 6326-79-0, name is 6-Bromoisatin, molecular formula is C8H4BrNO2, 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.

To R4 (500 mg, 2.21 mmol) in acetonitrile (15 mL) is added Mel (0.303 mL, 4.87 mmol) and K2CO3 (1.2 g, 8.68 mmol) and the reaction mixture stirred at 60 C for 45 min DCM and water is added and the aqueous layer extracted twice with DCM, the combined organic layers are washed with brine, dried and concentrated. Yield 65%. m/z 240/242 [M+H]+, rt 0.49 min, LC-MS Method b.

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

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GRUNDL, Marc; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; RIETHER, Doris; WIENEN, Wolfgang; WO2013/41497; (2013); A1;,
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Electric Literature 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: Step 1: To a 250 mL flask equipped with a silicone oil bubbler was added commercially available isatin (7.7 g, 50 mmol) and anhydrous DMF (80 mL). the mixture was cooled down to 0 oC. To this solution was added NaH (1.32 g, 55 mmol), followed by the addition of CH3I in 15 min. Upon completion of the reaction (monitored by TLC), the mixture was diluted with saturated NH4Cl solution and extracted with ethyl acetate. The organic layer was washed with water, dried over Na2SO4, filtered, and concentrated to yield the crude N-methylindoline-2, 3-dione, which was used directly in the next step. Step 2: The N-methylindoline-2, 3-dione (7.58 g, 47 mmol) was refluxed in NH2¡¤NH2-H2O ( 35 %) for 1h. Then the mixture was cooled to rt. The crude product was extracted with ethyl acetate. The combined organic layer was then dried over Na2SO4, purified by flash chromatography on silica gel (petroleum ether/ethyl acetate = 10:1). 1-Methylindolin-2-one was obtained as a pink solid.

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

Reference:
Article; Zhao, Jian-bo; Ren, Xinfeng; Zheng, Bu-quan; Ji, Jian; Qiu, Zi-bin; Li, Ya; Journal of Fluorine Chemistry; vol. 215; (2018); p. 44 – 51;,
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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 6341-92-0 as follows. SDS of cas: 6341-92-0

General procedure: The mixture of substituted isatins 1 (1 mmol), phthalic anhydride or succinic anhydride 2 (1 mmol), 1,3-dimethylurea (1,3-diethylurea) 3 (1.5 mmol), p-TSA?H2O (0.2 mmol), and CH3CN (3 mL) was put in a 25 mL flask and reacted under 80 C (monitored by TLC) about 5 h. After completion, the reaction the mixture was cooled to room temperature and the precipitate was obtained by filtration. Compound 4 was purified by recrystallization from EtOH.

According to the analysis of related databases, 6341-92-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Li, Lei; Xu, Hui; Yan, Lirong; Xu, Zhongyun; Ling, Zhi; Rong, Liangce; Tu, Shu-Jiang; Tetrahedron Letters; vol. 58; 25; (2017); p. 2468 – 2474;,
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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 56341-37-8 as follows. category: indolines-derivatives

To the mixture of 6-chloro-2-oxindole (3.9 g, 23 mmol) (Alfa) and 3-bromoo-2-fluorobenzaldehyde (4.7 g, 23 mmol) (Oakwood) in methanol (200 mL) was added piperidine (2 g, 24 mmol) (Aldrich) dropwise. The mixture was then heated at 80 C. for 2 h. After cooled to 4 C., the mixture was filtered and resulting precipitate was collected, dried to give E/Z-3-(3-bromo-2-fluoro-benzylidene)-6-chloro-1,3-dihydro-indol-2-one as a yellow solid (Yield 7.5 g, 92%).

According to the analysis of related databases, 56341-37-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bartkovitz, David Joseph; Chu, Xin-Jie; Ding, Qingjie; Graves, Bradford James; Jiang, Nan; Zhang, Jing; Zhang, Zhuming; US2011/130398; (2011); A1;,
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Adding a certain compound to certain chemical reactions, such as: 247564-59-6, name is 5,7-Difluoroindolin-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 247564-59-6, Product Details of 247564-59-6

Step 1:; 5,7-Difluorooxindole (prepared in a manner analogous to Example 62, steps 1-4 using 2,4,6-trifluoronitrobenzene instead of 2,6-difluoronitrobenzene) (0.64 g, 3.2 mmol) was dissolved in N,N-dimethylformamide (3 mL) and sodium hydride (0.24 g, 6.4 mmol, 60% wt suspension in mineral oil) was added in portions over 15 minutes and the mixture was stirred an additional 30 minutes. In a separate flask, [(2R,3R)-3-(3-fluorophenyl)oxiran-2-yl]methanol (1.08 g, 6.4 mmol, from Example 25 Step 3) was dissolved in N,N-dimethylformamide (3 mL) and titanium isopropoxide (1.89 mL, 6.4 mmol) was added and the mixture was stirred 30 minutes. The titanium isopropoxide/epoxide solution was then added to the solution of oxindole sodium salt dropwise and the mixture was stirred at room temperature for 24 hours. The mixture was then carefully quenched with 2 N aqueous hydrochloric acid and diluted with 200 mL of 2 N aqueous hydrochloric acid (use of hydrochloric acid is essential to prevent precipitation of titanium salts and subsequent emulsification). The mixture was extracted with ethyl acetate, the organic layers combined, washed with water, and saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified via Isco chromatography (Redisep, silica, gradient 20% to 100% ethyl acetate in hexane) to afford 1.02 g (87%) of 5,7-difluoro-1-[(1S,2S)-1-(3-fluorophenyl)-2,3-dihydroxypropyl]-3,3-dimethyl-1,3-dihydro-2H-indol-2-one as a sticky oil. MS (ES) m/z 365.12 (M+).

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; Wyeth; US2007/72897; (2007); 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. 110568-64-4, name is 6-Nitroisoindolin-1-one, A new synthetic method of this compound is introduced below., COA of Formula: C8H6N2O3

5-Amino-2,3-dihydroisoindol-l-oneH2N; [693] Iron powder (158mg, 2.83mmol), water (61uL), and HC1 (37percent, 5uL,0.566mmol) were added into the suspension of 5-nitro-2,3-dihydroisoindol-l-one (50.4mg,0.283mmol) in EtOH (754|^L). The above mixture was heated at 95¡ãC for 2h. After thattime, several drops of 7N NH3 in MeOH were added to basify the solution, and the solid wasfiltered off. The filtrate was concentrated in vacua to obtain a light-yellow solid that waspurified by preparative TLC eluting with 10percent MeOH/CH2Cl2 to give a light-yellow solid of5-amino-2,3-dihydroisoindol-l-one. ‘HNMR (CD3OD, 400 MHz): 5 = 7.48 (s, 1 H), 8.08 (s,2 H), 9.91 (s, 1 H), 10.66 (d, 1 H, J= 8.8 Hz). MS (ES+): m/z 149.21 (100) [MH1″]. HPLC: *R= 1.20 min (ZQ2000, polar_5 min).

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; OSI PHARMACEUTICALS, INC.; WO2006/17443; (2006); A2;,
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Indoline | C8H9N – PubChem

Related Products of 3484-35-3,Some common heterocyclic compound, 3484-35-3, name is 5-Methylindolin-2-one, molecular formula is C9H9NO, 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: The mixture of oxindole 1 (0.1 mmol), beta,gamma-unsaturated alpha-keto ester 2 (0.12 mmol),DABCO (0.02 mmol) in 1 mL H2O were stirred at room temperature. After stirringfor the indicated time, the mixture was extracted with ethyl acetate. The combinedorganic phase was dried over Na2SO4 and concentrated in vacuo. The residue wasfurther purified by washing with PE/EA to afford the desired products.

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

Reference:
Article; Han, Man-Yi; Pan, Ping; Sheng, Fei-Fei; Synlett; vol. 28; 11; (2017); p. 1378 – 1382;,
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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. 6780-38-7, name is 2-(1,3-Dioxoisoindolin-2-yl)acetyl chloride, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 2-(1,3-Dioxoisoindolin-2-yl)acetyl chloride

To a solution of SY1-182 (0.300 g, 1.34 mmol) in CH2Cl2 (5 mL) was added ammonia solution (7 N in MeOH, 0.57 mL, 4.02mmol) at 0 C. The mixture was allowed to warm to room temperature and stirred for 2 h. The mixture was diluted with hexanes and filtered. The solid product collected on frit was washed with water (20 mL) followed by hexanes (30 mL) and dried under vacuum to give the product as a white solid (0.200g, 74%).1H NMR (500 MHz, DMSO-d6) delta 7.91-7.90 (m, 2H), 7.87-7.85 (m, 2H) 7.69 (s, 1H), 7.25 (s, 1H), 4.15 (s, 2H).13C NMR (125 MHz, DMSO-d6) delta 167.92, 167.56, 134.53, 131.75, 123.17, 39.95. HPLC-MS (ESI+): m/z 431.1 [100%, (2M+Na)+], 227.2 [60%, (M+Na)+], 205.2 [80%, (M + H)+].

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 6780-38-7.

Reference:
Patent; H. LEE MOFFITT CANCER CENTER & RESEARCH INSTITUTE, INC.; BURNETTE, Pearlie; LAWRENCE, Harshani; LAWRENCE, Nicholas J.; (285 pag.)WO2017/161119; (2017); A1;,
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Some common heterocyclic compound, 84378-94-9, name is 4-Chloro-5-fluoroindoline-2,3-dione, molecular formula is C8H3ClFNO2, 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 4-Chloro-5-fluoroindoline-2,3-dione

2.00 g of 4-chloro-5-fluoroindole quinone was placed in 100 ml three-necked flask, 40 ml of toluene and 1.08 g of potassium borohydride were added in portions. The reaction was as follows: stirring and refluxing, reaction time: 5. Oh , The reaction temperature: 40 C, after the completion of the reaction, the solvent was removed by rotary evaporation to give 0.93 g of crude product of purple solid 4-C1-5-F-4 ‘-Cl-5’ -F-indirubin, The Ethanol was recrystallized to give a purple solid product, m.p.> 30 (TC (thermometer untreated).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 84378-94-9, its application will become more common.

Reference:
Patent; Northwest University; Wang, Culing; Liu, Jianli; Zhao, Danqing; Liu, Zhulan; Zhang, Ning; (10 pag.)CN103980182; (2016); B;,
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