Category: indolines-derivatives

Related Products of 14192-26-8, 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. 14192-26-8, name is Methyl 2-oxoindoline-6-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

The intermediate from Step D was esterified by heating in acidic methanol overnight. The resulting solution was concentrated under vacuum and the residue was dissolved in hot ethanol (75 mL). Methanol (20 mL) was added to redissolve some material that precipitated as the solution cooled. Sodium nitrite (1.50 g) was added, followed by concentrated hydrochloric acid (5 mL). The reaction was stirred for 2 h, and a further concentrated hydrochloric acid (2 mL) was added. The reaction was stirred overnight. Volatiles were removed under reduced pressure, water added, and the resulting yellow orange product was isolated by filtration and dried under vacuum to give the intermediate (2.1 g) as a yellow orange solid. [MH]+=221.

The chemical industry reduces the impact on the environment during synthesis Methyl 2-oxoindoline-6-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Alantos Pharmaceuticals, Inc.,; US2006/173183; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 89-40-7, The chemical industry reduces the impact on the environment during synthesis 89-40-7, name is 5-Nitroisoindoline-1,3-dione, I believe this compound will play a more active role in future production and life.

General procedure: The substrate (0.5 mmol), NiPd/MIL-101 catalyst (0.023g, Pd 0.2 mol%), and ethyl acetate (4 mL) were added to a Schlenk tube, and the mixture was vigorously stirred with an affixed hydrogenation balloon at room temperature. Following the reaction, the solid catalyst was removed from the solution by filtration and washed with ethyl acetate. The product yields were determined by gas chromatography-mass spectrometry (GC/MS, Shimadzu GCMS- QP5050A) with a 0.25 mm ¡Á 30 mDB-WAX capillary column. Parameters were as follows: initialoven temperature, 100 C, 1 min; ramp, 20 C/min; final temperature, 280 C; final time, 5 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-Nitroisoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Jian, Siping; Li, Yingwei; Cuihua Xuebao/Chinese Journal of Catalysis; vol. 37; 1; (2016); p. 91 – 97;,
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. 32692-19-6, name is 5-Nitroindoline, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 32692-19-6

5-Nitro-1-(2-(pyrrolidin-1-yl)ethyl)indoline (3) A solution of compound 2 (500 mg, 3.05 mmol) in DMF (10 mL) was treated with NaH (390 mg, 9.75 mmol, 60% wt in mineral oil) at 0 C. resulting in a bright orange suspension. The mixture stirred for 10 minutes, then 2-chloroethyl-pyrrolidine hydrochloride (566 mg, 3.33 mmol) was added and the reaction turned into a bright red suspension. The reaction was heated to 90 C. for 1 hour. After 1 hour, the reaction was allowed to cool to room temperature. Then it was diluted with water (20 mL), transferred to a separatory funnel and extracted with ethyl acetate (2*15 mL). The combined the organic layers were washed with brine (3*5 mL), dried (Na2SO4), filtered and concentrated. The residue was subjected to flash chromatography on silica gel using: 2.5% 2M NH3 in methanol: 97.5% CH2Cl2 to give a brown solid (400 mg, 50%). 1H-NMR (DMSO-d6) delta 7.96 (dd, J=2.4, 9.0 Hz, 1H), 7.80 (d, J=2.1 Hz, 1H), 6.47 (d, J=9.0 Hz, 1H), 3.73 (t, J=9.0 Hz, 2H), 3.41 (t, J=6.9 Hz, 2H), 3.04 (t, J=8.1 Hz, 2H), 2.62 (t, J=6.9 Hz, 2H), 2.58-2.48 (m, 4H), 1.70-1.64 (m, 4H).

According to the analysis of related databases, 32692-19-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MADDAFORD, Shawn; RAMNAUTH, Jailall; RAKHIT, Suman; PATMAN, Joanne; ANNEDI, Subhash C.; ANDREWS, John; DOVE, Peter; SILVERMAN, Sarah; Renton, Paul; US2008/234237; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 18711-13-2,Some common heterocyclic compound, 18711-13-2, name is 4,7-Dichloroindoline-2,3-dione, molecular formula is C8H3Cl2NO2, 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: The NiO-SiO2 catalyst (6.5 mol%) was added to a mixture of isatin (1 mmol), malononitrile (1 mmol), and 3-methyl-1-phenyl-1H-pyrazol-5-amine (1 mmol) in EtOH, and the reaction flask was placed in an oil bath and refluxed for the appropriate time. The progress of reaction was monitored by TLC. After the completion of the reaction, the heterogeneous catalyst was recovered from the reaction mixture by filtration. The filtrate was evaporated to afford the crude solid product which was later purified by column chromatography. The solid catalyst was washed with hot EtOH and then dried in oven to reuse.

The synthetic route of 18711-13-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yagnam, Swetha; Akondi, Adinarayana Murthy; Trivedi, Rajiv; Rathod, Balaji; Prakasham, Reddy Shetty; Sridhar; Synthetic Communications; vol. 48; 3; (2018); p. 255 – 266;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 496-12-8, These common heterocyclic compound, 496-12-8, name is Isoindoline, 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.

3-lodobenzoic acid (248 mg, 1.0 mmol), isoindoline (284 uL, 1.5 mmol), and triethylamine (420 uL, 3.0 mmol) were dissolved in 10 ml. of CH2CI2 and treated with HOBt (203 mg, 1.5 mmol) and EDC (288 mg, 1.5 mmol). The reaction was stirred at room temperature overnight. The reaction mixture was concentrated, diluted with EtOAc, and washed with water, 1N HCI, and brine. The organic layer was dried (MgSO4), filtered, and concentrated. The crude residue was purified by flash chromatography on silica gel (CH2CI2/Et0Ac) to yield 304 mg (87%) of the product as a tan solid. MS (+ESI): m/z 349.9 [M+H]+.

Statistics shows that Isoindoline is playing an increasingly important role. we look forward to future research findings about 496-12-8.

Reference:
Patent; WYETH LLC; LI, David, Zenan; O’NEIL, Steven, Victor; SPRINGER, Dane, Mark; ZEGARELLI, Benjamin, Miller; WO2010/124047; (2010); A1;,
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. 201940-08-1, name is tert-Butyl 5-bromoisoindoline-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 201940-08-1

Tris(dibenzylideneacetone)dipalladium(0) (228 mg, 0.25 mmol), 2-(di-tert-butylphosphino)biphenyl (149 mg, 0.50 mmol) and sodium tert-butoxide (1.34 g, 13.9 mmol) were added into a solution of 5-bromo-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester (2.97 g, 10 mmol) in toluene (15 mL). The reaction mixture was purged with argon for 5 minutes and then N-methylpiperazine (1.33 mL, 12 mmol) was added and the mixture and stirred at 80 C. for 4 hours. After the completion of the reaction (monitored by TLC) the solvent was removed under vacuum, water (3 mL) was added, and the reaction mixture was extracted with dichloromethane (3*30 mL). The combined organic extracts were dried over Na2SO4. The solvents were removed under vacuum and the residue was purified on silica gel (Biotage; eluting solvents 5% MeOH in dichloromethane) to afford tert-butyl 5-(4-methylpiperazin-1-yl)isoindoline-2-carboxylate as brown solid (1.75 g, 55% yield); 1H NMR (400 MHz, MeOH-d4) delta ppm 7.16-7.12 (m, 1H), 6.92-6.88 (m, 2H), 4.59-4.53 (m, 4H), 3.19-3.17 (m, 4H), 2.63-2.60 (m, 4H), 2.34 (s, 3H), 1.51 (9H, s).

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 201940-08-1.

Reference:
Patent; Malamas, Michael; Makriyannis, Alexandros; Lamani, Manjunath; Farah, Shrouq I.; US2019/152917; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6941-75-9, name is 5-Bromoisoindoline-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 6941-75-9, Computed Properties of C8H4BrNO2

EXAMPLE 5; Step 5A: Bromophthalimide 5a (13.0 g, 57.8 mmol) was added in six portions over 30 minutes to a stirred suspension of zinc powder (4.50 g, 69.2 mmol) and copper (II) sulfate pentahydrate (0.060 g, 0.25 mmol) in aqueous sodium hydroxide (2 M, 71 mL) at 0 C (ice-bath. ) The mixture was stirred at 0 C for an additional 30 minutes, and at room temperature for 2.5 h to complete the reaction. After filtering, the reaction solution was neutralized to pH 7 with 20% hydrochloric acid, diluted with 100 mL of ethanol, and then extracted with ethyl acetate. The extract was washed with brine, dried with MgS04 and concentrated in vacuo to afford 12.5 g (95%) of 5b as a yellow solid, LC-MS 210 (MH+-H20.)

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; NEUROCRINE BIOSCIENCES, INC.; WO2005/103039; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. name: 4-Bromoisatin

To 4-bromoindoline-2,3-dione (200 mg, 0.89 mmol) in 5 ml DMF was added 4- Fluorobenzylbromide (0.120 ml, 0.98 mmol) then add NaH (35 mg, 0.89 mmol) and stir at room temperature overnight. Work up by adding water and EtOAc and extract three times with EtOAc. Pool all organics and wash one time with brine then dry over sodium sulfate, filter and concentrate to dryness. The residue was purified by chromatography over silica gel (eluted with Hexanes/EtOAc 99:1 to 50:50) to provide 270 mg (90percent) of product.

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

Reference:
Patent; SCHERING CORPORATION; WO2009/73777; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. HPLC of Formula: C8H4FNO2

Weigh rapamycin (0.05mmol), isatin 3j (0.10mmol) and rhodium octanoate dimer(0.0005mmo),They were placed in a reaction flask, 2.0 mL of dry dichloromethane was added, and after stirring at room temperature for 5 minutes,Phenyldiazo 2a (0.10 mmol) was weighed and dissolved in dry dichloromethane (1.0 mL), and slowly added dropwise to the reaction system (about 1 hour), and stirring was continued for half an hour.The solvent was removed by rotary evaporation to give a crude product. The rapamycin analog I-j was obtained by column chromatography (eluent: petroleum ether: ethyl acetate = 1:10 to 1:4).The yield was 85%.

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

Reference:
Patent; Ha Yao Cihang Pharmaceutical Co., Ltd.; Changsha Tianci Bio-pharmaceutical Technology Co., Ltd.; Changsha Cihang Pharmaceutical Institute Co., Ltd.; Duan Yanwen; Huang Yong; Qiu Lin; Wen Zhongqing; Su Meng; (38 pag.)CN109776571; (2019); 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. 5394-18-3, name is 2-(4-Bromobutyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Product Details of 5394-18-3

To a cooled solution of 1 /-/-imidazole (200 mg, 3.085 mmol, 1.05 eq) in DMF (7 ml_), NaH 60% in mineral oil (136 mg, 3.393 mmol, 1.1 eq.) was added portionwise and the mixture was stirred for 10 min. Afterwards, a solution of 2-(4-bromobutyl)-2,3-dihydro-1 7Aisoindole-1,3-dione (870 mg, 3.085 mmol, 1 eq.) in DMF (3 ml.) was added dropwise. The reaction was continued at 60C for further 16 h. The reaction was quenched with water and diluted in AcOEt. The layers were separated. Organic layer was dried, filtered off and concentrated in vacuo. The residue was purified by FCC (SiHP, DCM: MeOH 95:5) to afford the title compound (323 mg, 1.2 mmol, yield 40%) as a white solid. ESI-MS: 270 [M+H]+ 1H NMR (300 MHz, Chloroform-o) d 7.89 – 7.85 (m, 2H), 7.77 – 7.73 (m, 2H), 7.50 (t, J= 1.1Hz, 1H), 7.07 (t, J= 1.1Hz, 1H), 6.93 (t, J= 1.3 Hz, 1H), 4.02 (t, J= 7.0 Hz, 2H), 3.74 (t, J= 6.8 Hz, 2H), 1.91 – 1.79 (m, 2H), 1.78 – 1.64 (m, 2H).

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; RYVU THERAPEUTICS S.A.; DOBRZANSKA, Monika Patrycja; ZAWADZKA, Magdalena Izabela; RADZIMIERSKI, Adam; TOPOLNICKI, Grzegorz Witold; CWIERTNIA, Grzegorz Wojciech; MAHAJAN, Tushar Ravindra; FABRITIUS, Charles-Henry; CHMIELEWSKI, Stefan; GLUZA, Karolina Maria; ALVAREZ, Jose; ROGACKI, Maciej Krzysztof; MROCZKOWSKA, Magdalena; (215 pag.)WO2019/238786; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem