Category: indolines-derivatives

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. 667463-64-1, name is 6-Bromo-1-methylindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 6-Bromo-1-methylindoline-2,3-dione

I-3.1 (397 mg, 1.65 mmol) and hydrazine hydrate (1 mL, 20.6 mmol) are heated to 100 C. for 1 h and at 125 C. for 1 h. To the cool reaction mixture DCM and water are added and the aqueous layer extracted twice with DCM. The combined organic layers are washed with brine, dried, concentrated and the residue purified via column chromatography (using solvent mixture cyclohexane/EA=3:1). Yield 65%. m/z 226 [M+H]+, m/z 224 [M+H]-, rt 0.58 min, LC-MS Method b.

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 667463-64-1.

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 446292-08-6 as follows. Formula: C22H19N3O6

4- [4-((S)-5-aminomethyl]-2-oxooxazolidin-3-yl)phenyl]morpholine-3-one (VII) 100 gm (wet) (0.2375 moles) 2-({(5S)-2-Oxo-3-[4-{3-oxo-4-morpholmyl)phenyl]- l,3- oxazolidin-5-yl}methyl)- lH-isoindole- l,3(2H)-dione (VI) is added in 500 ml water and (46.02 gm, 1,4845 moles) methyl amine solution (40% Aqueous). Reaction mass is stirred at 35C for 5 hours to get 4-[4-((S)-5-aminomethyl]-2-oxooxazolidin-3-yl) phenyl]morpholine-3-one (VII). Reaction mass is subjected for degassing (i. e. kept under vacuum) for 1 hour to remove excess methyl amine. This aqueous reaction mass is used as such for the preparation of Rivaroxaban without isolation.

According to the analysis of related databases, 446292-08-6, the application of this compound in the production field has become more and more popular.

Related Products of 39603-24-2, 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. 39603-24-2, name is 5,7-Dimethylindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A magnetically stirred mixture of naphthalene-2-amine (1.0mmol), isatin (1.0 mmol), dialkyl acetylenedicarboxylate (1.2 mmol) andanhydrous antimony trichloride (0.10 mmol) in dry acetonitrile (3 mL) taken ina 10 mL round bottom flask fitted with a reflux condenser under argonatmosphere and was refluxed for 5 h. After completion of the reaction, thereaction mixture was allowed to cool, quenched with water (10 mL) and extractedwith DCM (3 x 20 mL). The combined organic extracts were dried over anhydrousNa2SO4, filtered and volatiles were removed in vacuo. Thecrude residue was purified by column chromatography over silica gel (100-200mesh), eluting with 25 % ethyl acetate in petroleum ether to afford compound (4).

The synthetic route of 5,7-Dimethylindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Karmakar, Rajiv; Kayal, Utpal; Bhattacharya, Biswajit; Maiti, Gourhari; Tetrahedron Letters; vol. 55; 7; (2014); p. 1370 – 1372;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 24566-79-8, name is N-(6-Bromohexyl)phthalimide, molecular formula is C14H16BrNO2, 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

General procedure: To a suspension of the corresponding secondary amine (3.22 mmol) and anhydrous K2CO3 (765 mg, 5.48 mmol) in CH3CN (20 mL) was added the intermediates 3-5 (0.60 mmol). The mixture was refluxed for 6-8 h. The solvent was removed under reduced pressure. The residue was diluted with water (30 mL) and the mixture was extracted with dichloromethane (30 mL¡Á3). The combined organic phases were washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified on a silica gel chromatography in petroleum ether/acetone (20/1, v/v) to afford compound 7-9

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 24566-79-8, its application will become more common.

Reference:
Article; Song, Qing; Li, Yan; Cao, Zhongcheng; Qiang, Xiaoming; Tan, Zhenghuai; Deng, Yong; Bioorganic Chemistry; vol. 84; (2019); p. 137 – 149;,
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

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

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

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

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

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