Category: indolines-derivatives

Electric Literature of 101207-45-8, A common heterocyclic compound, 101207-45-8, name is 2-(4-Methylbenzyl)isoindoline-1,3-dione, molecular formula is C16H13NO2, 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.

Synthesis Intermediate 4 Dissolve 12.3g of 2-(4-methylbenzyl)-1H-isoindole-1,3-dione in chloroform, then add 8.7g of chlorosulfonic acid, Reaction at 80C for 3h; after the reaction, After washing with water and removing the solvent, 15.75 g of Intermediate 4 was obtained with a yield of 95%.

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; Zhengzhou Shouxing Pharmaceutical Institute Co., Ltd.; Deng Zhaoxi; (11 pag.)CN110627706; (2019); A;,
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Synthetic Route of 169037-23-4, These common heterocyclic compound, 169037-23-4, name is 5-(Trifluoromethoxy)indoline-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: The mixture of isatin 1 (29.4 mg, 0.2 mmol), antipyrine 2a (84.7 mg, 0.45 mmol) in 1mL H2O were stirred at 120 . Once the reaction completed (indicated by colorchange from red to white), the mixture was then cooled down to the room temperature.The insoluable solid mixture was filtered, washed by water and dried under vacuum to afford the desired product 4a in high pure form.

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

Reference:
Article; Zhang, Yong; Nie, Long-Jun; Luo, Liang; Mao, Jia-Xin; Liu, Jin-Xiang; Xu, Guo-Hai; Chen, Deliang; Luo, Hai-Qing; Tetrahedron; vol. 76; 7; (2020);,
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Adding a certain compound to certain chemical reactions, such as: 56341-37-8, name is 6-Chlorooxindole, 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 56341-37-8, SDS of cas: 56341-37-8

Step 1: Synthesis of 2.6-dichloro-1H-indole (2):1003131 To a stirred solution of 6-chloroindolin-2-one 1(500 mg, 2.99 mmol) in toluene (25 mL) under inert atmosphere were added N,N-dimethylaniline (362 mg, 2.99 mmol) and POC13 (918 g, 5.98 mmol) at RT; heated to 110 C and stirred for 1 h. The reaction was monitored by TLC; after completion of the reaction, the reaction mixture was quenched with 10% aq. NaHCO3 solution (30 mL) and extracted with EtOAc (2 x 30 mL). The combined organic extracts were dried over Na2SO4, filtered and concentrated under reduced pressure to obtain the crude. This was purified by silica gel column chromatography using 5% EtOAc/ Hexanes to afford compound 2 (350 mg, 63%) as an off-white solid. 1H NMR (400 MHz, CDC13): 5 8.09 (br s, 1H), 7.41 (d, J= 8.4 Hz, 1H), 7.28 (s, 1H), 7.09 (d, J= 8.4 Hz, 1H), 6.39 (s, 1H); MS (ES): m/z184 (M – Hj

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, 6-Chlorooxindole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PHARMAKEA, INC.; HUTCHINSON, John, Edward; LONERGAN, David; WO2015/77503; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 20870-78-4, name is 5-Bromoindolin-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 20870-78-4, category: indolines-derivatives

[0409] A mixture of an appropriately substituted oxindole, an appropriately substituted aldehyde (1 equivalent) and piperidine (excess) in ethanol (0.2M) was stirred at between room temperature to 100 C. After completion, the mixture was concentrated and then triturated with dil. HCl solution. The resulted precipitate was collected by vacuum filtration, washed with water and dried to give the desired product 5-Phenyloxindole (synthesised from 5-bromooxindole and phenyl boronic acid [Aldrich] via Suzuki coupling) was condensed with 3-(4-benzensulfonyl-2-formyl-5-methyl-1H-pyrrol-3-yl)-propionic acid (prepared as described above in the synthesis of aldehyde 2) and piperidine in ethanol to give the titled compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromoindolin-2-one, and friends who are interested can also refer to it.

Reference:
Patent; Sugen, Inc.; US2005/32871; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 6326-79-0, 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.

General procedure: A mixture of 2-bromoaniline or 3-bromoaniline (110 mmol, 18.9 g), chloral hydrate (118.8 mmol,19.6 g), anhydrous sodium sulfate (880 mmol, 125 g), and hydroxylamine hydrochloride (347.6mmol, 24.2 g) in water (700 mL) was heated under reflux for 25 min to form a yellow precipitate. 50mL of ethanol was added after that and left to boil for another 4 min before filtration. The resultedisonitrosoacetanilide was then heated with sulfuric acid (150 mL) at 70 C for about 10 min thenpoured into ice water to form an orange precipitate. When using 3-bromoaniline, an extra step ofseparation is required by solving the resulted mixture in 0.25 M NaOH (1 L), filtering it, then addingacetic acid (100 mL) to afford 4-bromoistain as a precipitate. 6-Bromoistin can be then obtained whenlowering the pH of the solution to 1 by hydrochloric acid 37%.All substituted bromo-isatins were methylated by stirring (22 mmol, 4.97 g) with sodiumhydride (2 mmol, 0.968 g) and dimethylsulfate (23.1 mmol, 2.19 mL) in dried DMF (50 mL) undernitrogen atmosphere. The resulting mixture was poured after 2 h in ice water (100 mL) to form anorange precipitate.The methylated bromo-isatins (2 mmol, 0.480 g) were treated after that with oxindole (2 mmol,0.226 g) in a 100:1 mixture of glacial acetic acid and hydrochloric acid 37% (12 mL) in reflux for about 3 h. Then, they were poured in ice water (50 mL) to afford 5-, 6- and 7-bromomeisoindigo. While 4′-, 5′-, 6′- and 7′-bromomeisoindigo were obtained by reacting unmethylated bromo-isatins(2 mmol, 0.452 g) with 1-methyloxindole (2 mmol, 0.294 g) in the same conditions. The resultedprecipitates were washed with water, ethanol (2 x 10 mL), and diethylether (2 10 mL) then dried.

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

Reference:
Article; Tegethoff, Jana; Bischoff, Roland; Saleh, Sawsan; Blagojevic, Biljana; Merz, Karl-Heinz; Cheng, Xinlai; Molecules; vol. 22; 9; (2017);,
Indoline – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 317-20-4, name is 7-Fluoroisatin, 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 317-20-4, name: 7-Fluoroisatin

(E) -N-Benzyl-2-nitro-N-phenylethylene-1,1-diamine (1 mmol) was added to a 25 ml round-And 7-fluoroindoline-2,3-dione (1.1 mmol) were added, toluene (15 ml), trichloroacetic acid (1 mmol)Mix with heating to 110 , the reaction was refluxed for 14 hours. TLC monitoring reaction until the point of complete disappearance of raw materials, the reaction solution was added50 mL of methylene chloride and 50 mL of saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous Na 2 SO 4 and theThe dried organic phase was concentrated under reduced pressure to dryness, and then 3 ml of acetone and 4 g of 100-200 mesh silica gelMix well, evaporated to dryness under reduced pressure, the sample was separated by silica gel column eluted with petroleum ether / ethyl acetate = 7: 1 to obtain a red solidThe product N-benzyl-8-fluoro-3-nitro-2- (phenylamino) quinoline-4-carboxamide (Compound 39) was obtained in 70% 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; Yunnan University; Yan Shengjiao; Wang Baoqu; Lin Jun; (25 pag.)CN107522659; (2017); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 17702-83-9, name is 2-(8-Bromooctyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 17702-83-9

a) Preparation of 8-pyrrolidinyloctylphthalimide 8-Bromooctylphthalimide (517 mg; 2.0 mmoles) and pyrrolidine (0.33 ml; 4.0 mmoles) were dissolved in anhydrous ethyl ether (5 ml). Reaction times and process as per Example 1. 348 mg of pure product were obtained. Yield 53percent.

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 17702-83-9.

Reference:
Patent; MEDIOLANUM FARMACEUTICI S.P.A.; EP575954; (1993); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 56341-37-8, 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. 56341-37-8, name is 6-Chlorooxindole belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

6-Chloro-1,3-dihydro-2H-indol-2-one (1.31 g, 7.85 mmol) and the compound (2.01 g, 7.85 mmol) obtained in Step 2 above were dissolved in methanol (40 ml) at room temperature and N,N-diisopropylethylamine (0.21 ml, 1.25 mmol) was added. After heating to reflux for 24 hours, saturated sodium bicarbonate solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with brine and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography [n-hexane:ethyl acetate=4:1 (v/v)] to give 2.53 g (82%) of the title compound as an orange solid.MS (FAB) m/z: 405 (M+H)+.

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, 6-Chlorooxindole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sugimoto, Yuuichi; Uoto, Kouichi; Wakabayashi, Takanori; Miyazaki, Masaki; Setoguchi, Masaki; Taniguchi, Toru; Yoshida, Keisuke; Yamaguchi, Akitake; Yoshida, Shoko; US2012/264738; (2012); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application 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.

A solution of N-methylisatin (81 mg, 0.5 mmol), phenylacethylene (77 mg, 0.75 mmol), CuI (19 mg, 0.1 mmol), and Cs2CO3 (245 mg, 0.75 mmol) in CH3CN (1.0 mL) was stirred at room temperature for 18 h. After aqueous extractive work up and column chromatographic purification process (CH2Cl2/EtOAc, 15:1) 1a was obtained as a pale yellow soild, 81 mg (61%). Other compounds were prepared similarly, and the spectroscopic data of unknown compounds 1b, 1d, and 1e are as follows.

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; Roh, Hwa Jung; Lim, Jin Woo; Ryu, Ji Yeon; Lee, Junseong; Kim, Jae Nyoung; Tetrahedron Letters; vol. 57; 38; (2016); p. 4280 – 4283;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 1254319-51-1,Some common heterocyclic compound, 1254319-51-1, name is 6-Bromo-2-methylisoindolin-1-one, molecular formula is C9H8BrNO, 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 stirred solution of 2,6-bis(benzyloxy)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- yl)pyridine 25-1 (2.19 g, 5.25 mmol) and 6-bromo-2-methylisoindolin-1-one (31-1) (474 mg, 2.10 mmol) in dioxane/water (30 mL), in a sealed tube, was degassed for 10 minutes under an argon atmosphere. PdCl2(dppf)-DCM (153 mg, 210 mumol) was added and the reaction was heated to 80 C for 10 h. TLC was checked in 30% ethyl acetate/hexane, which showed the complete consumption of starting material and formation of the desired spot at rf 0.4 in 30% ethylacetate- hexane. The reaction mixture was diluted with ethyl acetate, washed with water. The layers were separated and the organic layer was concentrated under reduced pressure. The crude residue was purified using combiflash (50% ethyl acetate/hexane) and concentrated to afford 6-(2,6-Bis- benzyloxy-pyridin-3-yl)-2-methyl-2,3-dihydro-isoindol-1-one (31-1) (725 mg, 1.66 mmol, 79% yield). LC MS: ES+ 437.2.

The synthetic route of 1254319-51-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; C4 THERAPEUTICS, INC.; PHILLIPS, Andrew, J.; NASVESCHUK, Chris, G.; HENDERSON, James, A.; LIANG, Yanke; HE, Minsheng; LAZARSKI, Kiel; VEITS, Gesine, Kerstin; VORA, Harit, U.; (794 pag.)WO2017/197046; (2017); A1;,
Indoline – Wikipedia,
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