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. 150560-58-0, name is 5-Isopropylindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 5-Isopropylindoline-2,3-dione

General procedure: Isatin based oxadiazole were synthesized in two steps, first semicarbazide(1 mmol, 0.71 g) and different substituted benzaldehydes(1 mmol) were mixed and reflux in methanol for 2-3 hrs. The completionof reaction was monitored by TLC. After completion of reaction,the intermediate was further cyclized by treating it with iodine andpotassium carbonate in 1, 4-dioxane to give a 2-aminooxadiazolemoiety. After drying, it was reacted with 5% Na2S2O3 (20 mL) and then it was extracted the desired organic compound from the reaction mixtureusing CH2Cl2/MeOH (10:1, 10 mL×4). The desired organiccompound was dried over anhydrous sodium sulphate and was purifiedusing petroleum ether and ethylacetate mixture as eluent through silicagel column chromatography afford the synthesis of correspondinganalogs. In the second step, 1 mmol of synthesized 2-aminooxadiazolewere refluxed with different substituted isatin in methanol in the presenceof few drops of glacial acetic acid for 3hrs. Reaction completionwas monitored through TLC. After completion of reaction, reactionmixture was washed with chloroform/hexane to obtained desired differentisatin based oxadiazole.

The synthetic route of 150560-58-0 has been constantly updated, and we look forward to future research findings.

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. 99365-40-9, name is 6-Bromoindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. category: indolines-derivatives

Compound 2 (2.1g, 10mmol), 6- bromo-indole (5.6g, 11mmol), glacial acetic acid (60ml) was addedThe two bottles, 3 drops of hydrochloric acid was added dropwise, under a nitrogen atmosphere, 130 refluxed for 24h, cooled to room temperature, adding a lot of water,Extracted with methylene chloride three times, the combined organic phase was washed with saturated sodium chloride, dried over anhydrous MgSO4, spin dry solvent,Petroleum ether: methylene chloride 1:1 (by volume) as eluent, column separation, spin dry to give a brown flaky solid(6.46g, 92%).

The synthetic route of 99365-40-9 has been constantly updated, and we look forward to future research findings.

Adding a certain compound to certain chemical reactions, such as: 16800-68-3, name is 1-Acetylindolin-3-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 16800-68-3, Product Details of 16800-68-3

3 – (2 – Fluorophenyl) propyne acid 4 – nitrophenyl-unitz (85.5 mg 0.3 mmol), was obtained. N- Acetylindole -3 -unitz 26.3 mg (0.15 mmol), the carbene-unitz (0.015 mmol), 3.96 mg, 1 diazabicycloundecene 8 – (-7 -) and methylene-methylene chloride shown in Formula 45 mul IV 0.3 mmol were placed in 3 ml a 25 ml unitunito-two-port 2h bottle, and reacted 30 C, under unituniteous conditions, and concentrated, under inert atmosphere protection, unitant-like conditions. The eluate fractions of all the products 10:1 detected were collected by chromatography with petroleum ether: ethyl acetate in the timetime as eluent column chromatography, and the solvent was evaporated to obtain the residue unit, 30 mg and gave rise 63% to unit_.

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; China Pharmaceutical University; Du Ding; Sun Kewen; (10 pag.)CN110156800; (2019); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 324-03-8, name is 6-Fluoroindoline-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. Formula: C8H4FNO2

A solution of 6-fluoroindoline-2,3-dione (2 g, 12.11 mmol) in dry DMF (100 ml) was cooled to 0 C., and NaH (60% w/w dispersion in mineral oil; 0.484 g, 12.11 mmol) was added portion wise over 10 minutes. The mixture was stirred at the same temperature for 10 minutes, then tert-butyl 2-bromoacetate (1.788 ml, 12.11 mmol) was added drop wise. The mixture was left warm to room temperature and stirred for 2 hours. DMF was evaporated under vacuum, and the crude was portioned between ethyl acetate (50 ml) and aqueous 1N HCl (40 ml). The aqueous phase was extracted with ethyl acetate (2¡Á50 ml), and the combined organic layers were dried over sodium sulfate, filtered and concentrate under vacuum. The crude was purified by flash chromatography on silica gel cartridge (petroleum ether:ethyl acetate=80:20) affording tert-butyl 2-(6-fluoro-2,3-dioxoindolin-1-yl)acetate(2.21 g, 7.91 mmol, 65% yield).

The synthetic route of 6-Fluoroindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chiesi Farmaceutici S.p.A.; ARMANI, Elisabetta; Amari, Gabriele; Capaldi, Carmelida; Carzaniga, Laura; La Porta, Elena; Guala, Matilde; US2013/102576; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one, A new synthetic method of this compound is introduced below., Product Details of 118289-55-7

Example 42 6-chloro-5-(2-(4-(thieno[2,3-c]pyridin-4-yl)piperazin-1-yl)ethyl)indolin-2-one The product of Reference Example 26 (200 mg, 0.632 mmol), 6-chloro-5-(2-chloroethyl)indolin-2-one (160 mg, 0.695 mmol), potassium carbonate (218 mg, 1.58 mmol), potassium iodide (157 mg, 0.948 mmol) were added to acetonitrile (7.5 ml) and the mixture was stirred at 80 C. overnight. The reaction mixture was concentrated and subjected to column chromatography to obtain a white solid (25 mg, yield: 8.7%). 1H-NMR (300 Hz, DMSO-d6): delta ppm 10.41 (s, 1H), 8.89 (s, 1H), 8.04 (m, 2H), 7.51 (d, 1H), 7.23 (s, 1H), 6.81 (s, 1H), 3.46 (s, 2H), 3.18 (brs, 4H), 2.85 (t, 2H), 2.71 (brs, 4H), 2.56 (t, 2H). ESI-MS (m/z): 413.3 [M+H]+.

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; 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;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 24566-79-8, These common heterocyclic compound, 24566-79-8, name is N-(6-Bromohexyl)phthalimide, 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: Amixture of the corresponding secondary amine 7a-d (5.5 mmol), anhydrous K2CO3 (6 mmol) andcompounds 2-4 (5 mmol) was added inCH3CN (20 ml). The mixture was heated at 65 C for 8-10 h. Thesolvent was evaporated under reduced pressure. Then water (25 mL) was added,and the mixture was extracted with dichloromethane (20 mL ¡Á 3). The combinedorganic phases were washed with saturated aqueous NaCl (30 mL), dried oversodium sulfate, and filtered. The solvent was evaporated under a vacuum. The residue was purified on a silicagel chromatography using mixtures of petroleum/acetone as eluent to obtain theoil products 8-10.

The synthetic route of 24566-79-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Pan, Wanli; Hu, Ke; Bai, Ping; Yu, Lintao; Ma, Qinge; Li, Tao; Zhang, Xu; Chen, Changzhong; Peng, Kelin; Liu, Wenmin; Sang, Zhipei; Bioorganic and Medicinal Chemistry Letters; vol. 26; 10; (2016); p. 2539 – 2543;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 496-12-8, 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. 496-12-8, name is Isoindoline, This compound has unique chemical properties. The synthetic route is as follows.

A solution of 5-bromo-2,4-dihydroxy-benzoic acid (520 mg, 2.33 mmol) in DMF (5 mL) was treated with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (471 mg, 2.45 mmol) then HOBt (362 mg, 2.68 mmol). After 25 min, 2,3-dihydro-1H-isoindole (0.5 mL, 2.63 mmol) was added then the mixture was stirred at r.t. for 18 h. The solvent was removed in vacuo then the residue was taken up in ethyl acetate and washed with 1N hydrochloric acid, saturated sodium bicarbonate solution and brine then dried (MgSO4) and concentrated. The residue was triturated with methanol to afford the title compound as a grey solid (328 mg, 44%). 1H NMR (DMSO-d6) 10.45 (1H, s), 10.32 (1H, s), 7.36 (1H, br. s), 7.35 (1H, s), 7.28 (3H, br. s), 6.59 (1H, s), 4.77 (2H, br. s), 4.71 (2H, br. s). MS: [M+H]+ 332/334.

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

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

Application of 446292-07-5, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 446292-07-5 name is (R)-2-(2-Hydroxy-3-((4-(3-oxomorpholino)phenyl)amino)propyl)isoindoline-1,3-dione, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Compound I was added to 39.5 g (0.1 mol), N,N-dimethylaniline 19.4 (0.16 mol), trichloromethane 120ml, added to 250ml of three bottles, stir to dissolve the solid. cooling to -20 C, temperature control at -20C ~ 10C slowly into the phosgene about 10.9g (0.11mol), and then heat for 10h. Nitrogen was bubbled through for 15 minutes. The crude product of the compound of formula (II) was obtained by distilling off the trichloromethane under reduced pressure by heating under reduced pressure, Filtration and drying gave 41.1 g of the compound of formula (II) as a white solid in 97.6% yield. HPLC, the purity was 98.95%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (R)-2-(2-Hydroxy-3-((4-(3-oxomorpholino)phenyl)amino)propyl)isoindoline-1,3-dione, and friends who are interested can also refer to it.

Reference:
Patent; Chongqing Ying Sikai Chemical Co., Ltd.; Chongqing Kerui Pharmaceutical (Group) Co., Ltd.; Huang Yuming; Wu Mingliang; Long Ping; Cheng Peng; Li Yang; Liu Junmin; Yue Xuerong; (10 pag.)CN106588905; (2017); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 59-48-3,Some common heterocyclic compound, 59-48-3, name is Indolin-2-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.

5-Acetyl-2-oxindole 2-Oxindole (3 g) was suspended in 1,2-dichloroethane and slowly treated with 3.2 mL of acetyl chloride. The resulting suspension was heated to 50 C. for 5 hours, cooled, and poured into water. The resulting precipitate was collected by vacuum filtration washed copiously with water and dried under vacuum to give 2.9 g (73% yield) of 5-acetyl-2-oxindole as a brown solid. 1H-NMR (360 MHz, DMSO-d6) delta 10.75 (s, br, NH), 7.83 (d, J=8 Hz, 1H), 7.78 (s, 1H, H-4) 6.88 (d, J=8 Hz, 1H),.3.53 (s, 2H, CH2), 2.49 (s, 3H, CH3).

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

Reference:
Patent; Sugen, Inc.; US6486185; (2002); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 239463-85-5, name is (R)-3-(5-(2-Aminopropyl)-7-cyanoindolin-1-yl)propyl benzoate (2R,3R)-2,3-dihydroxysuccinate, molecular formula is C26H31N3O8, 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

Preparation of 3- {7-cyano-5 – [(2R) -2 – ({2- [2- (2,2,2- trifluoroethoxy) phenoxy] ethyl} Propyl benzoate fumaric acid salt A mixture of 3- {5- (2R) -2-aminopropyl} -7-cyano-2,3-dihydro-1H- (2R, 3R) -monotartaric acid salt (monotartaric acid salt of the compound of formula (2)), potassium carbonate (80 g), and a mixed solvent of acetonitrile and dimethylacetamide ACN / DMAC = 500 mL / 500 mL) was warmed to 80 & lt; 0 & gt; C and stirred for 30 min. To the reaction mixture, 70 g of 2- [2- (2,2,2-trifluoroethoxy) phenoxy] ethyl methanesulfonate (compound of formula (III)) and 9.70 g of KI were added, Lt; / RTI & gt; The reaction mixture was cooled to room temperature and extracted with 1 L of ethyl acetate and 1.5 L of water. The organic layer obtained by layer separation was washed with 1 L of brine, dried over 40 g of anhydrous MgSO4 for 30 minutes, and then washed again with 200 mL of ethyl acetate. 23 g of fumaric acid was added to the obtained organic layer, and the mixture was heated to 50 DEG C, cooled to room temperature, and stirred for 2 hours. reaction The mixture was filtered, and the resulting solid was washed with 200 mL of ethyl acetate and dried in vacuo to yield 113 g of the title compound

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 239463-85-5, its application will become more common.

Reference:
Patent; Dasan Medichem Co., Ltd; Ryu, Hyung Sun; Sin, Dong Kyun; Kim, Sung Ho; Ahn, Jin Woo; Jo, Hey Jung; Moon, Sung Chul; Aum, Woon Yong; Kim, Jae Hyung; (12 pag.)KR2016/27536; (2016); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem