Indolines-derivatives

Adding a certain compound to certain chemical reactions, such as: 20780-77-2, name is 6-Iodoindoline-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 20780-77-2, Recommanded Product: 20780-77-2

General procedure: A mixture of isatin 1 (1.0 mmol), malononitrile or cyanoacetic ester 2 (1.0 mmol), phthalhydrazide (1.0 mmol), and NiCl2 (0.2 mmol) in PEG 600 (5 mL) was stirred at 100 C for the appropriate time (refPreviewPlaceHolderTable 2). After complete conversion as indicated by TLC, water was added and the product was extracted with ethyl acetate (2¡Á10 ml). The organic phase was dried over anhydrous Na2SO4, and concentrated under reduced pressure. The crude product was recrystallized from ethanol to afford the pure product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Iodoindoline-2,3-dione, and friends who are interested can also refer to it.

Reference:
Article; Zhang, Xiao-Nan; Li, Yong-Xiao; Zhang, Zhan-Hui; Tetrahedron; vol. 67; 38; (2011); p. 7426 – 7430;,
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. 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 169037-23-4

General procedure: A mixture of 5,6-dimethoxy-2-[(E)-1-arylmethylidene]-1-indanone (1, 0.364 mmol), thiazolidine-4-carboxylic (3, 0.364 mmol) and 1-morpholinoindoline-2,3-dione (2,0.364 mmol) was dissolved in methanol (1 mL) and irradiated for 2-3.5 min in a CEM microwave synthesizer (100 0C, 100 W). After completion of the reaction as evident from TLC, the mixture was poured into water. The precipitated solid was filtered and washed with water to afford the products 4a-i which was purified by recrystallisation.

According to the analysis of related databases, 169037-23-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Almansour, Abdulrahman I.; Ali, Sadath; Ali, Mohamed Ashraf; Ismail, Rusli; Choon, Tan Soo; Sellappan, Velmurugan; Elumalai, Karthi Keyan; Pandian, Suresh; Bioorganic and Medicinal Chemistry Letters; vol. 22; 24; (2012); p. 7418 – 7421;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 317-20-4, These common heterocyclic compound, 317-20-4, name is 7-Fluoroisatin, 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.

Add in a 25 mL round bottom flaskN, N’-dibenzyl-2-nitroethylene-1,1-diamine(1 mmol) and 7-fluoroIndoline-2,3-dione (1.1 mmol), toluene (15 ml) and acetic acid (1 mmol) were added under heating with magnetic stirringTo 110 C for 14 hours. The reaction was monitored by TLC, until the point of complete disappearance of raw materials, the reaction was added 50 ml of acetic acidEster and 50 ml of a saturated aqueous solution of sodium chloride. The organic layer was dried over anhydrous Na 2 SO 4. The dried organicThe phase was concentrated to dryness decompression pressure, after adding 3 ml of concentrated dry distillate acetone and 4 grams of 100 ~ 200 mesh silica gel Stirred byThe mixture was evaporated to dryness and loaded on a silica gel column eluting with petroleum ether / ethyl acetate = 7: 1 to give a yellow solid product, N-benzyl-2- (Benzylamino) -7-fluoro-3-nitroquinoline-4-carboxamide (Compound 31) in 80% yield.

Statistics shows that 7-Fluoroisatin is playing an increasingly important role. we look forward to future research findings about 317-20-4.

Reference:
Patent; Yunnan University; Yan Shengjiao; Wang Baoqu; Lin Jun; (25 pag.)CN107522659; (2017); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 41910-64-9, name is 4-Chloroindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. category: indolines-derivatives

General procedure: to a suspension of iv (1mmol) in acetonitrile (10ml) was added 5-fluoroindoline (1.2mmol). The reaction mixture was stirred at 40C for 16h and then evaporated to dryness under reduced pressure. Water (10mL) and diethylether (15mL) were added and the resulting mixture was stirred for 5min. The precipitate formed was filtered off and dried to give 7 (86%) as a white solid.

The synthetic route of 41910-64-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Certal, Victor; Halley, Frank; Virone-Oddos, Angela; Filoche-Romme, Bruno; Carry, Jean-Christophe; Gruss-Leleu, Florence; Bertin, Luc; Guizani, Houlfa; Pilorge, Fabienne; Richepin, Patrick; Karlsson, Andreas; Charrier, Veronique; Abecassis, Pierre-Yves; Vincent, Loic; Nicolas, Jean-Paul; Lengauer, Christoph; Garcia-Echeverria, Carlos; Schio, Laurent; Bioorganic and Medicinal Chemistry Letters; vol. 24; 6; (2014); p. 1506 – 1510;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 552330-86-6, The chemical industry reduces the impact on the environment during synthesis 552330-86-6, name is 5-Bromoisoindolin-1-one, I believe this compound will play a more active role in future production and life.

To a solution of 5-bromo-2,3-dihydro-isoindol-l-one (1 equiv) in dry dioxan (0.1 M) were added bis(pinacolato)diboron (1.1 equiv), potassium acetate (3.5 equiv) and dppf (0.05 equiv). The reaction mixture was degassed with nitrogen for 20 minutes. PdCl2(dppf) (0.05 equiv) was added to the reaction mixture, which was degassed for a further 5 minutes. The reaction mixture was heated to 70C for 2 hours under nitrogen then heated to 120C for 16 hours. The reaction mixture was partitioned between EtOAc and water. The aqueous phase was further extracted with EtOAc and the combined organic phases dried (MgSO4), filtered and concentrated in vacuo. The residue was dissolved in CH2Cl2 and hexane was added. The resulting suspension was filtered and the collected brown powder was dried and used without further purification.5-(4,4,5,5-Tetramethyl-[l,3,2]dioxaborolan-2-yl)-2,3-dihydro-isoindol-l-one: (94 % yield, 76 % purity, main impurity being the boronic acid 13 %) m/z (LC-MS, ESP): 260.4 [2M+H]+ R/T = 3.51 min

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-Bromoisoindolin-1-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; KUDOS PHARMACEUTICALS LIMITED; WO2008/23161; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 4403-36-5, 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. 4403-36-5, name is 2-(1,3-Dioxoisoindolin-2-yl)ethanesulfonylchloride belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 31 1-[5-(2-Phthalimidoethanesulfonamido)indole-2-carbonyl]-4-[N-methyl-N-(3-(1-methylethylamino)-2-pyridinyl)amino]piperidine (I) To a solution of 1-[5-aminoindole-2-carbonyl]-4-[N-methyl-N-(3-(1-methylethylamino)-2-pyridinyl)amino]piperidine (PREPARATION 56, 606 mg) in dry methylene chloride (5 ml) under nitrogen is added pyridine (127 mul, 1.05 equivalents) and 2-phthalimidoethanesulfonyl chloride (400 mg). The mixture is stirred at 20-25 for 3 days and then diluted with methylene chloride (40 ml) and water (20 ml). The layers are separated and the organic phase is washed with saline (15 ml), dried over sodium sulfate, and concentrated under reduced pressure to give a residue which is then chromatographed on silica gel (230-400 mesh, 85g, 8 psi), eluding with a gradient of methanol/chloroform (1/99-2.5/97.5). The appropriate fractions (Rf =0.33, TLC, methanol/chloroform, 5/95) are pooled and concentrated to give the title compound, NMR (CDCl3) 10.33, 7.80, 7.76-7.63, 7.35, 7.22, 6.95, 6.85, 6.69, 4.65, 4.51, 4.13, 3.60-3.40, 3.40-2.90, 2.64, 1.94, 1.65 and 1.22 delta.

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-(1,3-Dioxoisoindolin-2-yl)ethanesulfonylchloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; The Upjohn Company; US5599930; (1997); A;,
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. 141452-01-9, name is Methyl indoline-5-carboxylate, A new synthetic method of this compound is introduced below., SDS of cas: 141452-01-9

To a stirred solution of 4,6-dichloro-5-methylpyrimidine (101 mg, 0.62 mmol) in n- propanol (2.0 ml.) was added 2,3-dihydro-1 H-indole-5-carboxylic acid methyl ester {Bioorg. Med. Chem. Lett. 2008, 18, 5684 – 8) (100 mg, 0.56 mmol). The resulting yellow solution was heated at reflux (100 degrees Celsius). After 4 hours at reflux the reaction mixture was cooled to room temperature and was concentrated in vacuo. The reside was purified by flash chromatography, eluting with a gradient mixture of 10-40% ethyl acetate to heptane to give methyl 1-(6-chloro-5-methylpyrimidin-4-yl)indoline-5- carboxylate as a white solid (60 mg).

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; PFIZER INC.; DAROUT, Etzer; DENINNO, Michael, Paul; FUTATSUGI, Kentaro; GUIMARAES, Cristiano, Ruch, Werneck; LEFKER, Bruce, Allen; MASCITTI, Vincent; MCCLURE, Kim, Francis; MUNCHHOF, Michael, John; ROBINSON, Ralph, Pelton, Jr.; WO2010/128414; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 13220-46-7,Some common heterocyclic compound, 13220-46-7, name is 4-Methylindolin-2-one, molecular formula is C9H9NO, 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.

EXAMPLE 21 3-[2,4-Dimethyl-5-(4-methyl-2-oxo-1,2-dihydroindol-3-ylidene-methyl)-1H-pyrrol-3-yl]-propionic acid 3-(2-Carboxyethyl)-2,4-dimethyl-5-formylpyrrole (97.5 mg), 74 mg 4-methyl-2-oxindole, and 75 muL piperidine in 3 mL of ethanol were heated at 95 C. for 5 hours. The reaction mixture was cooled and concentrated. The residue was suspended in 6 N of aqueous hydrochloric acid. The precipitate was filtered, washed with water to pH 6 and dried in a vacuum oven overnight to give 60 mg (37%) of the title compound as a green solid. 1H-NMR (360 MHz, DMSO-d6): delta 13.41 (s, br, 1H, NH-1′), 12.03 (s, br, 1H, COOH), 10.72 (s, br, 1H, NH-1), 7.50 (s, 1H, H-vinyl), 7.01 (t, J=7.82 Hz, 1H, H-6), 6.79 (d, J=7.82 Hz, H-5), 6.74 (d, J=7.82 Hz, 1H, H-7), 2.64 (t, J=7.76 Hz, 2H, CH2CH2COOH), 2.56 (s, 3H, CH3), 2.34 (t, J=7.76 Hz, 2H, CH2CH2COOH), 2.29 (s, 3H, CH3), 2.18 (s, 3H, CH3); MS m/z (relative intensity, %) 325 ([M+1]+, 100).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Methylindolin-2-one, its application will become more common.

Reference:
Patent; Sugen, Inc.; US6395734; (2002); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 118289-55-7, 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.

100.0 g of 6-Chloro-5-(2-chloroethyl) oxindole, 133.39 g of 3-(l-Piperazinyle)- 1,2-benzisothiazole hydrochloride, 105.94 g of sodium carbonate and 1500 mL of water were taken in round bottom flask and heated to 1000C to HO0C for 24-26 hours. The reaction mixture was cooled and maintained for 30 min. The solid was filtered and washed with water. The wet solid was further slurried with water followed by adjusting the pH of the reaction mass with dilute acetic acid to 6.0 to 7.5 and maintain the reaction mass for 1-2 hours. The solid was filtered and washed with water. The wet solid was treated with isopropanol 1100 mL in round bottom flask and heated at 750C to 850C for 2 hours. The reaction mixture was cooled, the obtained solid was filtered and washed with isopropanol. The wet solid was dried at 6O0C to 650C for 8-10 hours to obtain crude Ziprasidone base.

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; CADILA HEALTHCARE LIMITED; SHAH, Niraj, Shyamlal; DWIVEDI, Shriprakash, Dhar; WO2010/73255; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 446292-07-5,Some common heterocyclic compound, 446292-07-5, name is (R)-2-(2-Hydroxy-3-((4-(3-oxomorpholino)phenyl)amino)propyl)isoindoline-1,3-dione, molecular formula is C21H21N3O5, 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.

100 g (i?)-2-(2-hydroxy-3-(4-(3-oxo-morpholino) phenyl amino) propyl) isoindoline-l,3-dione of Formula (F) and MDC (1000 ml) were added to RBF at 25C to 35C and heated to 40C to 45C. Further, 61 g Nu,Nu-Carbonyl diimidazole (CDI) and 0.5 g DMAP were added and stirred for 3-4 hours. Excess MDC was evaporated under reduced pressure. The reaction mass was cooled to 25C to 35C followed by addition of dilute HCl solution and stirred for 1 hour and finally filtered and washed with 2 x 200 ml water to afford title compound as (S)-2-((2-oxo 3-(4-(3-oxo- mo holno)phenyl)oxazolidin-5-yl)methyl)isoindoline-l,3-dione of Formula (I).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (R)-2-(2-Hydroxy-3-((4-(3-oxomorpholino)phenyl)amino)propyl)isoindoline-1,3-dione, its application will become more common.

Reference:
Patent; CADILA HEALTHCARE LIMITED; DWIVEDI, Shriprakash, Dhar; PRASAD, Ashok; PAL, Daya, Ram; SHARMA, Mukul, Hari, Prasad; JAIN, Kuldeep, Natwarlal; PATEL, Naitik, Bharatbhai; WO2013/98833; (2013); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem