Category: indolines-derivatives

Electric Literature of 611-09-6, These common heterocyclic compound, 611-09-6, name is 5-Nitroindoline-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: First, 0.01g of the CoFe2O4(at)SiO2(at)SO3H was dispersed for 30min and after that an amount of 1mmol from isatin, malononitrile and dimedone with ethanol/water (ratio 1:1) were mixed, and the final mixture was placed in 80C at the reflux condition. After completing the reaction by passing a certain time, the con -taining solution was separated by centrifuging and the crude product extracted and washed with ethyl acetate, and then Na 2 SO 4 was added to dehydrating the product. After that, the solvent was removed by using a rotary evaporator and finally the product recrystallized in hot ethanol to gain the pure product. Moreo -ver, the catalyst was washed and applied for several times to examine reusability. Structural assignments of the products are based on their 1 HNMR, 13 CNMR and IR spectra.

Statistics shows that 5-Nitroindoline-2,3-dione is playing an increasingly important role. we look forward to future research findings about 611-09-6.

Reference:
Article; Zamani-Ranjbar-Garmroodi, Bardia; Nasseri, Mohammad A.; Allahresani, Ali; Hemmat, Kaveh; Research on Chemical Intermediates; vol. 45; 11; (2019); p. 5665 – 5680;,
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Adding a certain compound to certain chemical reactions, such as: 446292-08-6, name is (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-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 446292-08-6, Computed Properties of C22H19N3O6

5L three-necked flask with a compound of formula (II)(100, (^, 24011111101),Anhydrous ethanol 6001111 (6ml / g), stirring, suspended state,Room temperature dropMethylamine solution(40% aqueous solution, 56 g, 720 mmo 1),The reaction system gradually heated to 60 ~ 63 C, keep the temperature stirring for 2 hours,(20 ~ 25 C), suction filter, filter cake methanol washing, drying and drying for 6 hours, to give the formula (20 ~ 25 C), and then cooled to 55 C, III) hydrochloride of the structural compound in a yield of 85%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione, and friends who are interested can also refer to it.

Reference:
Patent; SHENZHEN HYBIO PHARMACEUTICAL CO., LTD.; YUAN, HUIXING; XIAO, QING; LI, GUOTAO; MA, YAPING; YUAN, JIANCHENG; (21 pag.)CN104016975; (2017); B;,
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Adding a certain compound to certain chemical reactions, such as: 19155-24-9, name is 3,3-Dimethylindolin-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 19155-24-9, Computed Properties of C10H11NO

Step 4: 3,3-dimethyl-2,3-dihydro-1H-indole Under a nitrogen atmosphere a solution of 6.20 mL (6.20 mmol) of a 1M solution lithium aluminium hydride in THF and 10 mL THF was slowly added dropwise to 1.00 g (6.20 mmol) 3,3-dimethyl-1,3-dihydro-indol-2-one in 50 mL THF. Then the reaction mixture was heated to 60 C. for 1 h. After cooling to 0 C., 3 mL ice water were slowly added dropwise. 20 g sodium sulphate were added and the mixture was suction filtered. The solution was evaporated down i. vac. Yield: 0.80 g (88% of theory) ESI-MS: m/z=148 (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, 3,3-Dimethylindolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/195954; (2011); A1;,
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Synthetic Route of 50727-04-3, 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. 50727-04-3, name is 5-Methoxyisoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A stirred solution of 4-methoxyphthalimide (21.3 g, 0.12 mol) in anhydrous tetrahydrofuran (425 ml) at 0 C. was treated dropwise with a solution of borane in tetrahydrofuran (1M, 340 ml, 0.34 mol) and the resulting mixture was stirred and held at reflux for 16 hours. The mixture was cooled to 0 C., methanol (150 ml) was added dropwise followed by 5M hydrochloric acid (150 ml) and the mixture was stirred and held at reflux for 3 hours. Upon cooling to room temperature the organic solvent was removed in vacuo, the mixture was diluted with water (750 ml) and was extracted with dichloromethane (3¡Á750 ml). The aqueous layer was basified to pH 12 or above by the addition of 5M sodium hydroxide, extracted with dichloromethane (3¡Á750 ml) and the combined extracts were evaporated to dryness in vacuo to afford 5-methoxyisoindoline (8.34 g, 47%) as a brown oil. 1H NMR (DMSO-d6) 7.13 (1H, d), 6.84 (1H, d), 6.74 (1H, dd), 4.05 (2H, s), 4.01 (2H, s), 3.73 (3H, s). MS: [M+H]+ 150.

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-Methoxyisoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; US2010/152184; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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 118289-55-7 as follows. COA of Formula: C10H9Cl2NO

Example 1 6-chloro-5-(2-(4-(2,3-dihydrobenzo[b]thiophen-4-yl)piperazin-1-yl)ethyl)indolin-2-one 6-chloro-5-(2-chloroethyl)indolin-2-one (120 mg, 0.52 mmol), the product of Reference Example 12 (115 mg, 0.52 mmol), potassium carbonate (215 mg, 1.56 mmol), potassium iodide (86 mg, 0.52 mmol) and acetonitrile (5 ml) were added to the flask and the mixture was stirred at 85 C. overnight. The reaction mixture was concentrated and subjected to column chromatography to obtain a white solid (120 mg, yield: 56%). 1HNMR (300 MHz, DMSO-d6): delta ppm 10.42 (brs, 1H), 7.21 (s, 1H), 7.07 (t, 1H), 6.90 (d, 1H), 6.80 (s, 1H), 6.69 (d, 1H), 3.45 (s, 2H), 3.30 (t, 2H), 3.14 (t, 2H), 2.74-2.95 (m, 6H), 2.59 (brs, 4H), 2.50 (t, 2H). ESI-MS (m/z): 414.2 [M+H]+.

According to the analysis of related databases, 118289-55-7, the application of this compound in the production field has become more and more popular.

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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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. 86626-38-2, name is 4-Bromoindoline, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 4-Bromoindoline

A mixture of above obtained 4-bromoindoline (759 mg, 3.81 mmol), and (Boc)20 (976 mg, 4.48 mmol) in MeCN (8 mL) was stirred at room temperature overnight. After evaporated, the residue was dissolved in ethyl acetate (40 mL), washed with water (3 x 20 mL) and brine (1 x 20 mL). The organic layer was concentrated and purified by column chromatography on silica gel (petroleum ether) to give 0601-177(840 mg, 74%>) as a white solid. 1H-NMR (400 MHz. DMSO-Patent; CURIS, INC.; BAO, Rudi; LAI, Chengjung; QIAN, Changgeng; WO2011/130628; (2011); A1;,
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Related Products of 39755-95-8, 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. 39755-95-8, name is 5-Methoxyisatin, This compound has unique chemical properties. The synthetic route is as follows.

Intermediate 20: 5-Methoxyindolin-2-one[0507] A solution of 5-methoxyisatin (1.0 g, 5.6 mmol) in hydrazine hydrate (85%, 6.0 mL) was refluxed for 3 h. After the mixture was concentrated, the residue was treated with 50%> aqueous NaOH solution (40.0 mL) and the resulting mixture was stirred at room temperature for 48 h. The mixture was poured into water and extracted with diethyl ether. The combined extracts were washed with brine, dried over anhydrous Na2S04 and concentrated. The residue was purified by flash column chromatography (PE/EA = 10: 1 to 2:1) to afford 184 mg of the title compound as a white solid (20% yield).

The chemical industry reduces the impact on the environment during synthesis 5-Methoxyisatin. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ZENOBIA THERAPEUTICS, INC.; BOUNAUD, Pierre-Yves; NIENABER, Vicki; STEENSMA, Ruo, W.; LOWE, John, A., III; WO2012/178015; (2012); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 3891-07-4, name is 2-(2-Hydroxyethyl)isoindoline-1,3-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. category: indolines-derivatives

To a mechanically stirred suspension of NaH (15g, 0. 375 mol, 60% dispersion in mineral oil) in THF (250 mL) and DMF (25 mL) was added N- (2-hydroxyethyl)-phtalimide (43g, 0. 225 mol). The mixture was stirred at room temperature for about 4 h and then cooled to about 0C in an ice bath. Ethyl-4- chloroacetate (21. 4 mL, 0. 15 mol) in THF (4 mL) was then added via an addition funnel over a period of about 0. 5 h and the resulting mixture allowed to stir overnight. The mixture was then poured into a 2 L sepratory funnel containing 500 mL ice water and 700 mL EtOAc and separated. The organic layer was washed 2x with 500 mL of water and dried over MGS04. The solution was then filtered through a 4-inch plug of silica and then CONCENTRATED IN VACUO. The resulting yellow oil was then dissolved in 250 mL CH3CN and washed 2x with 30 mL hexane. The CH3CN layer was the concentrated in vacuo to yield 19. 4g (40. 5%) OF 4- [2- (1, 3-DIOXO-1, 3-DIHYDRO-ISOINDOL-2-YL)-ETHOXY]-3-OXO-BUTYRIC acid ethyl ester as a yellow oil. This crude compound was used for the next step

The synthetic route of 2-(2-Hydroxyethyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SYNTA PHAMACEUTICALS CORP.; WO2005/25507; (2005); A2;,
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Some common heterocyclic compound, 101207-45-8, name is 2-(4-Methylbenzyl)isoindoline-1,3-dione, molecular formula is C16H13NO2, 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. Product Details of 101207-45-8

REFERENTIAL EXAMPLE 11 To 50.3 g of 4-phthalimidomethyltoluene, were added 39 g of N-bromosuccinimide (NBS), 1.5 g of benzoyl peroxide (BPO), and 500 ml of carbon tetrachloride. The mixture was heated under reflux for one hour. The reaction mixture was cooled in ice, filtered from insolubles, and concentrated under reduced pressure. The residue was recrystallized from methanol to yield 40 g of colorless needle crystals of 4-phthalimidomethylbenzyl bromide; m.p. 129-131 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 101207-45-8, its application will become more common.

Reference:
Patent; Torii & Co. Ltd.; US4598077; (1986); A;,
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20780-72-7, name is 4-Bromoisatin, 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. Quality Control of 4-Bromoisatin

General procedure: At first, 0.5mmol of aryl aldehyde or isatin was added to a mixture of ketone (cyclohexanone or acetone, 5equiv), 15 or 20molpercent catalyst, 30 or 40molpercent acid, and 2.0mL of solvent at reaction temperature. The reaction mixture was stirred for the indicated time and then purified through flash column chromatography on a silica gel (petroleum ether/ethyl acetate) to afford the pure products.

The synthetic route of 20780-72-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Xu, Biao; Li, Lei; Gou, Shaohua; Tetrahedron Asymmetry; vol. 24; 24; (2013); p. 1556 – 1561;,
Indoline – Wikipedia,
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