Category: indolines-derivatives

Related Products of 118289-55-7, The chemical industry reduces the impact on the environment during synthesis 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one, I believe this compound will play a more active role in future production and life.

Example 15 5-(2-(4-(benzo[b]thiophen-4-yl)piperazin-1-yl)ethyl)-6-chloroindolin-2-one hydrochloride A mixture of 6-chloro-5-(2-chloroethyl)indolin-2-one (332 mg, 1.45 mmol), the product of Reference Example 1 (370 mg, 1.45 mmol), sodium carbonate (461 mg, 4.35 mmol), iodine sodium (216 mg, 1.45 mmol) and water (5 ml) was stirred under reflux for 24 hours. The reaction was cooled to room temperature, extracted with methylene chloride and water. The organic phase was dried over anhydrous sodium sulfate, filtered, concentrated and subjected to column chromatography to obtain an oil. Hydrogen chloride-ethanol solution was added thereto under stirring, the resulting salt was slurried in isopropanol, filtered to give a pale yellow solid (308 mg, yield: 51%). 1HNMR (400 MHz, DMSO-d6): delta ppm 11.04 (brs, 1H), 10.55 (s, 1H), 7.77 (d, 1H), 7.71 (d, 1H), 7.50 (d, 1H), 7.32 (t, 1H), 7.29 (s, 1H), 6.98 (d, 1H), 6.88 (s, 1H), 3.71 (d, 2H), 3.57 (d, 2H), 3.50 (s, 2H), 3.38 (m, 4H), 3.21 (m, 4H). ESI-MS (m/z): 412.2 [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-Chloro-5-(2-chloroethyl)indolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SHANGHAI INSTITUTE OF MATERIA MEDICA, CHINESE ACADEMY OF SCIENCES; SUZHOU VIGONVITA LIFE SCIENCES CO., LTD.; TOPHARMAN SHANDONG CO., LTD.; JIANG, Hualiang; WANG, Zhen; LI, Jianfeng; ZHANG, Rongxia; HE, Yang; LIU, Yongjian; BI, Minghao; LIU, Zheng; TIAN, Guanghui; CHEN, Weiming; YANG, Feipu; WU, Chunhui; WANG, Yu; JIANG, Xiangrui; YIN, Jingjing; WANG, Guan; SHEN, Jingshan; (70 pag.)US2017/158680; (2017); A1;,
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Related Products of 5332-26-3, 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. 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

1-2: Dimethyl 2-(4-tert-butoxycarbonylpiperazin-1-yl)-2-(1,3-dioxo-1,3-dihydroisoindol-2-ylmethyl)malonate; 3.5 g (87 mmol) of sodium hydride are added portionwise to a solution of 25 g (87 mmol) of dimethyl 2-(4-tert-butoxycarbonylpiperazin-1-yl)malonate in 250 ml of tetrahydrofuran cooled to 2 C. The reaction medium is stirred at ambient temperature for 30 minutes and then brought back to 2 C., before adding, dropwise, 21 g (87 mmol) of 2-bromomethylisoindole-1,3-dione in 200 ml of tetrahydrofuran. The reaction medium is stirred at ambient temperature for 20 h, treated by adding 500 ml of water and then extracted with ethyl acetate. The organic phase is dried over magnesium sulfate, filtered, and concentrated under vacuum.The crude product obtained is purified by chromatography on silica gel, elution being carried out with a 70/30 heptane/ethyl acetate mixture. 27.5 g (73%) of dimethyl 2-(4-tert-butoxycarbonylpiperazin-1-yl)-2-(1,3-dioxo-1,3-dihydroisoindol-2-ylmethyl)malonate are obtained in the form of a white solid.

The chemical industry reduces the impact on the environment during synthesis 2-(Bromomethyl)isoindoline-1,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GALDERMA RESEARCH & DEVELOPMENT; US2012/323006; (2012); 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 18711-13-2 as follows. Product Details of 18711-13-2

General procedure: Sulfonated-beta-cyclodextrin (beta-CD-SO3H) (76 mg, 0.06 mmol) was dissolved in water (5 mL) at RT by stirring to get the clear solution in 50 mL round bottom ask. Further, isatin 2 (0.31 mmol) and tryptamine 1a/isotryptamine 1b (0.31 mmol) were added to the solution under constant stirring and mixture was heated at 80 C for 8-12 h. The progress of the reaction was monitored by TLC. After completion of reaction, it was cooled to room temperature, water was added to it. The aqueous phase was extracted with ethylacetate. The organic extracts were combined, washed with brine and dried over sodium sulfate. The solvent was evaporated in vacuo and the crude product obtained was puried by column chromatography using chloroform/methanol (99:1) as an eluent furnishing the product. The spectral and analytical data of all the reported products is consistent with the previous (6c,d,f) reports.

According to the analysis of related databases, 18711-13-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Urmode, Tukaram D.; Dawange, Monali A.; Shinde, Vaishali S.; Kusurkar, Radhika S.; Tetrahedron; vol. 73; 30; (2017); p. 4348 – 4354;,
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Adding a certain compound to certain chemical reactions, such as: 18711-15-4, name is 4,6-Dichloroisatin, 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 18711-15-4, HPLC of Formula: C8H3Cl2NO2

a. 5,7-Dichloro-2H-3,1-benzoxazine-2,4(1H)-dione To a stirred solution of 4,6-dichloro-1H-indole-2,3-dione (5.00 g, 23.2 mM) in acetic acid (21 mL) and acetic anhydride (21 mL) at 80 C. was added in small portions chromium trioxide (4.12 g, 41.3 mM). The temperature of the reaction mixture was maintained between 80-90 C. during the addition of the chromium trioxide. After the addition was complete, the reaction mixture was diluted with water (100 mL) and then filtered to separate the precipitated solids. The solids were washed thoroughly with water and then dried to obtain the title compound as a yellow solid (4.13 g, 72%); MS(CI): 232 (M+H).

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; Imperial Chemical Industries, PLC; US5599814; (1997); A;,
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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. Formula: C8H4FNO2

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.

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

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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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. 334952-09-9, name is 2-Oxoindoline-6-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 334952-09-9

2a III 2-04 Intermediate 2a (3.3g) and 2-aminophenol (2g) are added to polyphosphoric acid (2Og) and heated to 150C for 2 hours. The reaction is then cooled to room temperature and then poured onto ice. The mixture is then neutralized with concentrated ammonia. The resulting precipitate is collected via filtration and then dissolved in DCM:EtOH (9:1). The resulting EPO solution is dried over Na2SO4, filtered and the solvent is removed in vacuo to yield the desired compound III (660mg).

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 334952-09-9.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2006/64044; (2006); A1;,
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Adding a certain compound to certain chemical reactions, such as: 39603-24-2, name is 5,7-Dimethylindoline-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 39603-24-2, Recommanded Product: 39603-24-2

General procedure: An equimolar mixture of dipolarophile 1/7 (1 mmol), isatin 2a-e/acenaphthenequinone 11 (1 mmol) and sarcosine 3/1,3-thiazolane-4-carboxylic acid 5 (1 mmol) in 2,2,2-trifluoroethanol (10 ml) was refluxed forthe appropriate time (30-40 min). After completion of the reaction asindicated by (TLC), the solid precipitates were filtered and washed withethanol to furnish pure corresponding dispiropyrrolidine/thiapyrrolizidinederivatives. Synthesized compounds were well characterized by 1H NMR, 13CNMR, Mass and single crystal X-ray analysis of representative compounds.

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, 5,7-Dimethylindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Dandia, Anshu; Singh, Ruby; Khan, Shahnawaz; Kumari, Sukhbeer; Soni, Pragya; Tetrahedron Letters; vol. 56; 30; (2015); p. 4438 – 4444;,
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These common heterocyclic compound, 675109-26-9, name is 6-Bromoisoindolin-1-one, 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. name: 6-Bromoisoindolin-1-one

6-(4-Hydroxy-but-1-ynyl)-2,3-dihydro-isoindolin-1-oneTo a mixture of 6-Bromo-2, 3-dihydro-isoindolin-1-one (3Og, 0.14mole), bis (triphenylphosphine) palladium dichloride (5 g, 0.007 mole), CuI (2.6 g, 0.01 mole), dry Et3N (700 mL) in dry DMF (700 mL) was added 3-butyn-1-ol (21.3 mL, 0.28 mole) slowly drop- wise. The reaction mixture was bubbled with argon for 20 min and heated at 100 C for 24 h. The solvent was evaporated and the crude residue was washed with DCM (100 mL), filtered and dried to 6-(4-Hydroxy-but-1-ynyl)-2,3-dihydro-isoindolin-1-one as a pale grey solid (24 g, 85%). 1H-NMR (DMSO-d6, 300 MHz): delta 8.6 (1H1 s), 7.5-7.6 (2H, d), 7.5 (1H,s), 4.9 (1H, t), 4.3 (2H1 s), 3.6-3.7 (2H, t), 2.4-2.6 (2H, t); MS: M+1: 202 (201)

The synthetic route of 6-Bromoisoindolin-1-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2008/20306; (2008); A2;,
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Synthetic Route of 423116-18-1, 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. 423116-18-1, name is 2-(4-Oxocyclohexylmethyl)isoindole-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

3-tert-Butyl-11-phthalimidomethyl-7,14,15-trioxadispiro[5.1.5.2]pentadecane (OZ384). A solution of O-methyl 4-tert-butylcyclohexanone oxime (2.74 g, 15 mmol) and 4-phthalimidomethylcyclohexanone (2.57 g, 10 mmol) in cyclohexane (100 ml) and CH2Cl2 (100 ml) was treated with ozone according to the general procedure. The reaction mixture was concentrated, triturated with ethanol (50 ml), and filtered. The cake was purified by flash chromatography (silica gel, 10% EtOAc in hexanes) to afford trioxolane OZ384 (0.41 g, 10%) as a colorless solid. mp 175 C. dec; 1H NMR (500 MHz, CDCl3) delta0.86 (s, 9H), 0.94-1.05 (m, 1H), 1.21-1.42 (m, 4H), 1.47-2.02 (m, 13H), 3.56 (d, J=7.3 Hz, 2H), 7.70-7.74 (m, 2H), 7.81-7.87 (m, 2H); 13C NMR (125.7 MHz, CDCl3) delta24.50, 27.66, 27.81, 32.29, 33.43, 34.54, 35.59, 43.10, 47.23, 108.74, 108.89, 123.24, 132.00, 133.92, 168.53. Anal. Calcd for C25H33NO5: C, 70.23; H, 7.78; N, 3.28. Found: C, 70.46; H, 7.90; N, 3.43.

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, 2-(4-Oxocyclohexylmethyl)isoindole-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MEDICINES FOR MALARIA VENTURE MMV; US2005/256185; (2005); A1;,
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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. 356068-93-4, name is (Z)-5-((5-Fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. category: indolines-derivatives

To a stirred solution of compound 109 (0.5 g, 1.67 mmol) in DMF( 40 mL) at O0C was added etaOBt (0.34 g, 2.5 mmol), triethylamine (0.94 mL, 6.68 mmol), ECDI etaC1 (0.48 g, 2.5 mmol) and compound 303 (0.44 g, 2.0 mmol) successively. The mixture was stirred overnight at room temperature, evaporated, diluted with water (50 mL), brine (50 mL) and saturated aqueous sodium bicarbonate(50 mL). The peta of solution was adjusted to 11-12 with 1OM NaOH. The mixture was filtered, washed with water, dried to obtain desired product 304 as a yellow solid (630 mg, 75%). LCMS: 504 [M+l]+, 1H NMR (DMSO-J6): delta 2.39 (s, 3H), 2.41 (s, 3H), 3.59 (m, 2H), 3.69 (s, 3H), 4.15 (t, J= 4.5 Hz, 2H), 6.45 (d, IH), 6.94 (m, 4H), 7.65 (m, 6H), 10.87 (s, IH), 13.66 (s, IH).

The synthetic route of 356068-93-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CURIS, INC.; WO2008/33747; (2008); A2;,
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