Category: indolines-derivatives

17702-83-9, name is 2-(8-Bromooctyl)isoindoline-1,3-dione, 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: 2-(8-Bromooctyl)isoindoline-1,3-dione

2-(8-(6-Amino-8-((6-iodobenzo[d][1,3]dioxol-5-yl)thio)-9H-purin-9-yl)octyl)isoindoline-1,3-dione (16c) (Scheme 4). 200 mg (0.484 mmol) of Compound 11 was dissolved in DMF (8 mL). 466 mg (1.43 mmol) of Cs2CO3 and 819 mg (2.42 mmol) N-(8-bromooctyl)phthalimide were added and the mixture was sonicated for 1.5 h. Solvent was removed under reduced pressure and the resulting residue was purified by preparatory TLC (CH2Cl2:MeOH:AcOH, 15:1:0.5) to give 120 mg (34percent) of Compound 16c. 1H NMR (500 MHz, CDCl3) delta 8.29 (s, 1H), 7.84 (dd, J = 5.5, 3.1 Hz, 2H), 7.70 (dd, J = 5.5, 3.1 Hz, 2H), 7.28 (s, 1H), 6.87 (s, 1H), 6.29 (br s, 2H), 5.96 (s, 2H), 4.18 (t, J = 7.5 Hz, 2H), 3.67 (t, J = 7.3 Hz, 2H), 1.62-1.77 (m, 4H), 1.25-1.36 (m, 8H); MS (ESI) m/z 671.3 [M+H]+.

The synthetic route of 17702-83-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sloan Kettering Institute For Cancer Research; Cornell University; CHIOSIS, Gabriela; PILLARSETTY, Nagavarakishore; LEWIS, Jason S.; LARSON, Steven M.; TALDONE, Tony; ALPAUGH, Mary L.; (168 pag.)EP3208615; (2017); A2;,
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Synthetic Route of 923590-95-8, 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 923590-95-8 as follows.

General procedure: 4-Bromoisoindoline hydrochloride (3.0 g, 13 mmol, 1 eq) was suspended in dry DCM (50 ml), and then TEA (5.4 ml, 39 mmol, 3 eq) was added. Reaction mixture was cooled to 0C in an ice-bath, and then benzyl chloroformate (2.7 ml, 19 mmol, 1 .5 eq) dissolved in 10 ml DCM was added dropwise. Reaction was carried out under inert gas (nitrogen) atmosphere while stirring at room temperature for 3h. Reaction mixture was extracted thrice with saturated NaHCC solution, then once with water and with saturated NaCl solution. Organic phase was dried over anhydrous Na2S04, and then concentrated under reduced pressure to obtain white solid which was dried under vacuum. (0165) White solid, yield: 90% (3.8 g), Ci6Hi4BrN02, MW 332.19, monoisotopic mass 331 .02, [M+H]+ 332.2, UPLC Rt = 8.12. 1H NMR (300 MHz, CDCU) d (ppm) 4.73 (dd, J= 1 1 .6, 1 .4 Hz, 2H), 4.79-4.89 (m, 2H), 5.22 (d, J = 2.2 Hz, 2H), 7.09-7.50 (m, 7H).

According to the analysis of related databases, 923590-95-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CELON PHARMA S.A.; UNIWERSYTET JAGIELLONSKI; INSTYTUT FARMAKOLOGII POLSKIEJ AKADEMII NAUK; KAMINSKI, Krzysztof; GRYCHOWSKA, Katarzyna; CANALE, Vittorio; BOJARSKI, Andrzej J.; SATALA, Grzegorz; LENDA, Tomasz; POPIK, Piotr; MATLOKA, Mikolaj; DUBIEL, Krzysztof; MOSZCZYNSKI-PETKOWSKI, Rafal; PIECZYKOLAN, Jerzy; WIECZOREK, Maciej; ZAJDEL, Pawel; (69 pag.)WO2019/97282; (2019); A1;,
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Adding a certain compound to certain chemical reactions, such as: 611-09-6, name is 5-Nitroindoline-2,3-dione, 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 611-09-6, COA of Formula: C8H4N2O4

A mixture of 5-nitroisatin 22a (5.0 g, 26.0 mmol), 2, 2′-dimethylpropane-1, 3-diol (2.69 g, 25.9 mmol) and a catalytic amount ofp-TSA was suspended in cyclohexane (35 mL) and refluxed with azeotropic removal of water using Dean-Stark apparatus, overnight. The reaction mixture was cooled to room temperature and the solid that separeted was filtered, washed with dilute aqueous sodium bicarbonate, water and then air dried to give 22b. Yield 6. 5g, 90%.

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-Nitroindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE ROCKEFELLER UNIVERSITY; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; WO2005/41954; (2005); 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 7477-63-6 as follows. COA of Formula: C8H4ClNO2

General procedure: A mixture of isatins 1 (1 mmol), substituted 1H-pyrazol-5-amine 2 (1 mmol), 6-aminopyrimidine-2,4(1H,3H)-dione 3 or 6-amino-1,3-dimethylpyrimidine-2,4(1H,3H)-dione 5 (1 mmol), H2O(6 mL), and HOAc (2 mL) was placed in a 25-mL flask andstirred at 90 ¡ãC (monitored by thin layer chromatography (TLC)) for about 7 h. Afterreaction completion, the mixture was cooled to room temperature and the precipitateobtained by filtration. Compounds 4 or 6 were further purified by recrystallizationfrom DMF.

According to the analysis of related databases, 7477-63-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Dai, Lei; Mao, Kaimin; Pan, Zhengbing; Rong, Liangce; Research on Chemical Intermediates; vol. 45; 2; (2019); p. 769 – 788;,
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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. 324-03-8, name is 6-Fluoroindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 324-03-8

General procedure: A 25-mL flask, equipped with a magnetic stirring bar, was charged with 2-(1,3-dithiolan-2- ylidene)acetonitrile 1a (143 mg, 1.0 mmol), isatin 2a (74 mg, 0.5 mmol), and MeCN (3.0 mL), followed by addition of a solution of I2 (25 mg, 0.1 mmol) in MeCN (1.0 mL). The reaction mixture was stirred at 80 C for 12 h. After 1a was consumed, as indicated by TLC, the reaction mixture was quenched with saturated aqueous Na2S2O3 (1.0 mL) and water (20.0 mL), and stirred for another 10 min. The fully precipitated solid was filtered and washed with water (20.0 mL). Then it was further washed with petroleum ether-ethyl acetate (1/1, V/V, 20.0 mL) and dried under vacuum to afford 3a.

The synthetic route of 324-03-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liang, Deqiang; Li, Xiangguang; Yang, Juan; Li, Yanni; Wang, Baoling; Cheng, Ping; Synthetic Communications; vol. 46; 23; (2016); p. 1924 – 1931;,
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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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Reference of 169037-23-4,Some common heterocyclic compound, 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, molecular formula is C9H4F3NO3, 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.

(a) Step 1 Aqueous sodium hydroxide (0.0888 g, 2.22 mmol, 2 mL) was heated to 50C, and added with 5-trifluoromethoxyisatin (0.500 g, 2.16 mmol). The mixture was stirred at 50C for 1 hour, and then cooled on ice. The reaction mixture was added with sodium nitrite (0.149 g, 2.16 mmol), and then added dropwise with a solution of concentrated sulfuric acid (0.413 g, 4.21 mmol) in ice-cooled water (3.5 mL), and the mixture was stirred for 1 hour under ice cooling. Then, the mixture was added dropwise with an ice-cooled solution of tin(II) chloride dihydrate (1.17 g, 5.18 mmol) in concentrated hydrochloric acid (1.7 mL). The mixture was stirred overnight at room temperature, and then filtered to obtain a pale brown solid (0.638 g).

The synthetic route of 169037-23-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The University of Tokyo; Riken; NAGANO Tetsuo; OKABE Takayoshi; KOJIMA Hirotatsu; SAITO Nae; NAKANO Hirofumi; ABE Masanao; TANAKA Akiko; HONMA Teruki; YOKOYAMA Shigeyuki; TSUGANEZAWA Keiko; YUKI Hitomi; EP2565192; (2013); A1;,
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Adding a certain compound to certain chemical reactions, such as: 19727-83-4, name is 6-Nitroindoline, 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 19727-83-4, Recommanded Product: 6-Nitroindoline

At room temperature, 6-nitroindoline (99 mg, 0.6 mmol) was added to the reaction tube containing p-methylthiophenol (62 mg, 0.5 mmol) and dimethyl sulfoxide (1.0 mL). After stirring uniformly at room temperature, riboflavin 1 (0.025 mmol, 8 mg) and elemental iodine (0.05 mmol, 13 mg) were added in sequence, and then vacuum oxygen protection was applied. After the reaction tube was reacted at 60C for 24 hours, it was cooled to room temperature, and saturated sodium thiosulfate solution was added to quench the reaction. Then, the reaction solution was extracted with ethyl acetate, and then washed with saturated sodium chloride solution, and the organic layers were combined and dried with anhydrous sodium sulfate, and the organic layer was concentrated by rotary evaporation.Finally, it was purified by column chromatography (n-hexane: ethyl acetate = 30: 1) to obtain a yellow solid 6-nitro-3-(4-methylphenylthio)indole 106 mg, yield 75%.

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; Zhejiang University of Technology; Jiang Xinpeng; Zhao Zongchen; Yu Chuanming; (8 pag.)CN111100056; (2020); A;,
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Electric Literature of 480-91-1,Some common heterocyclic compound, 480-91-1, name is Isoindolin-1-one, molecular formula is C8H7NO, 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.

[0195] To 2,3-dihydro-isoindol-l-one (250.Omg, 1.85mmol) in acetonitrile (9mL) was added propargyl bromide (308.6uL, 2.77mmol) and cesium carbonate (2.4g, 7.39mmol) and the mixture was allowed to stir at 80C for two hours. An aqueous workup was done to provide the title compound (303.3mg, 96%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Isoindolin-1-one, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; NPS PHARMACEUTICALS, INC.; WO2006/20879; (2006); A1;,
Indoline – Wikipedia,
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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. 1504-06-9, name is 3-Methyloxindole, A new synthetic method of this compound is introduced below., Recommanded Product: 3-Methyloxindole

General procedure: To a Schlenk tube were added 2-oxindoles 1 (0.3 mmol),Cu(OAc)2 (0.03 mmol), DTBP (0.6 mmol), and 1,4-dioxane (2mL). Then the tube was stirred at 120 C under air for the indicatedtime until complete consumption of starting material asmonitored by TLC analysis. After the reaction was finished, thesolution was concentrated under reduced pressure, and themixture was purified by flash column chromatography oversilica gel (hexane/ethyl acetate) to afford the desired products 2and was analyzed by 1H NMR and 13C NMR spectroscopy andHRMS (see Supporting Information).Typical Data for Representative Compound – 3,3?-Dimethyl-[3,3?-biindoline]-2,2?-dione (2a)d.r. = 19:1, brown solid (0.0701 g, 80% yield). 1H NMR (400 MHz,DMSO-d6): delta = 10.48 (s, 1.9 H), 10.31 (s, 0.1 H), 8.01 (d, J = 3.2Hz, 0.1 H), 7.80 (t, J = 5.1 Hz, 0.1 H), 7.40 (d, J = 1.6 Hz, 0.1 H),7.33 (d, J = 7.6 Hz, 0.1 H), 7.09 (d, J = 7.6 Hz, 1.9 H), 6.96 (t, J = 7.6Hz, 1.9 H), 6.78 (t, J = 7.2 Hz, 1.9 H), 6.54 (d, J = 7.6 Hz, 1.9 H),1.58 (s, 5.7 H), 1.55 (s, 0.3 H).13C NMR (100 MHz, DMSO-d6): delta =179.8, 141.4, 132.3, 128.3, 123.4, 121.5, 109.4, 50.4, 17.6. HRMS(ESI): m/z calcd for C18H17N2O2+ [M + H]+: 293.1285; found:293.1284.

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; Huang, Yi-Ling; Bao, Wen-Hui; Ying, Wei-Wei; Chen, Wei-Ting; Gao, Le-Han; Wang, Xin-Ye; Chen, Gan-Ping; Ge, Guo-Ping; Wei, Wen-Ting; Synlett; vol. 29; 11; (2018); p. 1485 – 1490;,
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