Category: indolines-derivatives

These common heterocyclic compound, 59-48-3, name is Indolin-2-one, 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. SDS of cas: 59-48-3

5-Iodo-2-oxindole 2-Oxindole (82.9 g) was suspended in 630 mL of acetic acid with mechanical stirring and the mixture cooled to 10 C. in an ice water bath. Solid N-iodosuccinimide (175 g) was added in portions over 10 minutes. After the addition was complete the mixture was stirred for 1.0 hour at 10 C. The suspended solid which had always present became very thick at this time. The solid was collected by vacuum filtration, washed with 100 mL of 50% acetic acid in water and then with 200 mL of water and sucked dry for 20 minutes in the funnel. The product was dried under vacuum to give 93.5 g (36%) of 5-iodo-2-oxindole containing about 5% 2-oxindole by proton NMR.

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

Reference:
Patent; SUGEN, Inc.; US2003/69421; (2003); A1;; ; Patent; Sugen, Inc.; US6051593; (2000); 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. 56341-37-8, name is 6-Chlorooxindole, A new synthetic method of this compound is introduced below., Application In Synthesis of 6-Chlorooxindole

To the mixture of 6-chloro-2-oxindole (4.4 g, 26 mmol) (Crescent) and 3-chloro-5-fluorobenzaldehyde (4.2 g, 26 mmol) (Aldrich) in methanol (200 mL) was added piperidine (2.3 g, 26 mmol) (Aldrich) dropwise. The mixture was then heated at 80 C. for 2 h. After cooled to 4 C., the mixture was filtered and resulting precipitate was collected, dried to give E/Z-6-chloro-3-(3-chloro-5-fluoro-benzylidene)-1,3-dihydro-indol-2-one as a yellow solid (Yield 7.5 g, 92%).

The synthetic route of 56341-37-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bartkovitz, David Joseph; Chu, Xin-Jie; Ding, Qingjie; Graves, Bradford James; Jiang, Nan; Zhang, Jing; Zhang, Zhuming; US2011/130398; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 552330-86-6, name is 5-Bromoisoindolin-1-one, molecular formula is C8H6BrNO, 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 552330-86-6

To R8 (100 mg, 0.47 mmol) in anhydrous dioxane (8 mL) is added R5 (180 mg, 0.71 mmol) and potassium acetate (140mg, 1.43 mmol). The mixture is purged with Argon, PdCl2(dppf) (40 mg, 0.049 mmol) added and heated to 80 C for 1.5 h. The reaction mixture is diluted with EA and water, the organic layer washed with brine, dried and concentrated. The crude product is carried on. m/z 260 [M+H]+, rt 0.64 min LC-MS Method b.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 552330-86-6, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GRUNDL, Marc; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; RIETHER, Doris; WIENEN, Wolfgang; WO2013/41497; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 959235-95-1, 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. 959235-95-1 name is 6-(Trifluoromethoxy)indoline, 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.

A mixture of 6-(trifluoromethoxy)indoline [CAS 959235-95-1 ] (5 g, 24.6 mmol), 2-(4-chlorophenyl)acetic acid [CAS 1878-66-6] (4.2 g, 24.6 mmol), HATU (14.3 g, 36.9 mmol) and diisopropylethylamine (12.2 mL, 73.8 mmol) in DMF (60 mL) was stirred at room temperature for 20 h. The mixture was poured out slowly into stirring H2O (275 mL) and the resulting suspension was stirred for 50 minutes. The solids were filtered off and washed (4x) with H2O. The solid residue was taken up in toluene (125 mL), filtered over a paper filter, and the filtrate was evaporated under reduced pressure. The solid residue was stirred up in Et2O/heptane 2/1 (30 mL), filtered off, washed (3x) with Et2O/heptane 1/1 , and dried under vacuum at 50C to provide 2-(4-chlorophenyl)-1 -(6-(trifluoromethoxy)indolin-1 -yl)ethanone 1 b (7.33 g).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-(Trifluoromethoxy)indoline, and friends who are interested can also refer to it.

Reference:
Patent; JANSSEN PHARMACEUTICALS, INC.; KATHOLIEKE UNIVERSITEIT LEUVEN; BONFANTI, Jean-Francois; KESTELEYN, Bart, Rudolf, Romanie; BARDIOT, Dorothee, Alice, Marie-Eve; MARCHAND, Arnaud, Didier, M; COESEMANS, Erwin; FORTIN, Jerome, Michel, Claude; MERCEY, Guillaume, Jean, Maurice; RABOISSON, Pierre, Jean-Marie, Bernard; (153 pag.)WO2018/215315; (2018); 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. 603-62-3, name is 3-Nitrophthalimide, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H4N2O4

3-Nitrophthalimide (LOOGR) was taken into a hydrogenation vessel and dissolved using 500ML of dimethylformamide. Raney nickel catalyst (20gr, wet) was added to the solution and subjected to hydrogenation conditions initially at 20-30C UNDER 20-40psi. After the exothermic nature of the reaction was over, hydrogen pressure was increased to 40-60psi and the temperature to 40-50C. After the hydrogen uptake is over sample was drawn from the reaction mass and checked for the absence of 3-nitrophthalimide by TLC. The reaction mixture was filtered while hot and the catalyst removed by filtration. Solvent was removed from the filtrate under reduced pressure at 60-80C. Water (500ML) was added to the residue and the mixture stirred for 20-30MIN. The product was isolated by filtration and dried at 60-70C to get a yellow crystalline solid of 3-aminophthalimide (80gr, 95%). Melting point: 262-4C.

According to the analysis of related databases, 603-62-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NATCO PHARMA LIMITED; VENKAIAH CHOWDARY, Nannapaneni; WO2004/43919; (2004); 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 13220-46-7 as follows. Quality Control of 4-Methylindolin-2-one

Example 3 3-(3H-Isobenzofuran-1-ylidene)-4-methyl-1,3-dihydro-indol-2-one To a solution containing 4-methyloxindole (0.15 g, 1.02 mmol) and phthalide (0.178 g, 1.33 mmol) in 3.0 mL DMF was added 2.14 mL of sodium hexamethyldisilazane (1.0 M in tetrahydrofuran (THF)) over 1 min. The solution was stirred at room temperature for 30 min and then poured into 50 mL of 4% HCl to give a yellow solid. The aqueous mixture was extracted with EtOAc and the organic phase washed with saturated NaHCO3, H2O, dilute HCl, brine and the solution dried with Na2SO4. The solvent was removed in vacuo and the solid obtained was purified by chromatography (silica gel, CHCl3/EtOAc, 7:3). The solid obtained was recrystallized from EtOAc/hexanes to afford the title compounds (3.8 mg) as a yellow solid. 1H NMR (500 MHz, CDCl3) delta ppm 2.58 (s, 3H) 5.62 (s, 2H) 6.70 (d, J=7.81 Hz, 1H) 6.86 (d, J=7.32 Hz, 1H) 7.07 (t, J=7.57 Hz, 1H) 7.45 (m, 1H) 7.56 (m, 2H) 7.68 (s, 1H) 9.70 (d, J=6.83 Hz, 1H).

According to the analysis of related databases, 13220-46-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Allergan, Inc.; US2004/19098; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 4702-13-0, 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. 4702-13-0, name is N-Phthaloylglycine belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Phthaloyl glycine (1.0 g, 4.9 mmol) in a 100 mL eggplant-shaped flask was dissolved in dichloromethane (20 mL). Afterwards, oxalyl chloride (2.5 g, 19.6 mmol) and DMF (50 mg) were added. The reaction solution was stirred at room temperature for 30 min and then concentrated. 1.2 g of a pale yellow solid were obtained, which was applied directly to the next step without purification.

The synthetic route of N-Phthaloylglycine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Yabao Pharmaceutical Group Co., Ltd.; Suzhou Yabao Pharmaceutical Research And Development Co., Ltd.; Song Yang; Qian Xiaoxin; Sun Xiaolin; Li Sailei; Zhu Lin; Zhang Xiyu; Zhang Fei; Wang Peng; (37 pag.)CN109232403; (2019); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 480-91-1, name is Isoindolin-1-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 480-91-1, category: indolines-derivatives

Example 7: Illustrative Preparation of 5-member Glutarimide Scheme 23: (1973) (1974) Step-1 To a stirred solution of 23-2 (448 mg, 3.37 mmol) and 23-1 (1000 mg, 3.37 mmol) and Potassium carbonate (931 mg, 6.74 mmol) in Acetone (20.0 mL ). It was stirred at room temperature for 16 hours. It was diluted with water and extracted with ethyl acetate. Organic part was dried over sodium sulfate, concentrated under reduced pressure and purified by column chromatography using (silica, gradient, 0%-30% ethyl acetate in hexane to afford 3 as off white solid. Yield-20%; LC MS: ES+ 349.3.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Isoindolin-1-one, and friends who are interested can also refer to it.

Reference:
Patent; C4 THERAPEUTICS, INC.; PHILLIPS, Andrew, J.; NASVESCHUK, Chris, G.; HENDERSON, James, A.; LIANG, Yanke; CHEN, Chi-li; DUPLESSIS, Martin; HE, Minsheng; LAZARSKI, Kiel; (980 pag.)WO2017/197051; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6872-06-6, name is 2-Methylindoline, 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 6872-06-6, name: 2-Methylindoline

General procedure: In a 2-neck RBF, 1 (20 mg, 0.0005 mmol) and TMNO (45 mg, 0.6 mmol) were suspended in toluene (4 mL) and to this solution indoline (60 mg, 0.5 mmol) was added. The reaction mixture was then heated to 100 oC for 20 h and it was filtered and solvent evaporated. The crude product obtained was purified by column chromatography using hexane/ethylacetate (7:1) as eluent to give pure indole (47 mg, 79%). A similar procedure was used for the other indolines and N-heterocycles.

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-Methylindoline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kumaran, Elumalai; Leong, Weng Kee; Tetrahedron Letters; vol. 59; 44; (2018); p. 3958 – 3960;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 22190-33-6, 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. 22190-33-6 name is 5-Bromoindoline, 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.

1 , 1 -Dimethylethyl 5-bromo-2,3-dihvdro-1 H-indole-1 -carboxylateTo a stirred solution of 5-bromo-2,3-dihydro-1 H-indole (30 g, 151 mmol) and DMAP (0.4 g, 3.27 mmol, 0.02 equiv) in 150 mL of MeCN at room temperature was added Boc20 (43 g, 197 mmol, 1.3 equiv) in one portion. The mixture was stirred at rt. After 10 min, the mixture gradually became a suspension. After 3 h, the suspension was filtered. The cake was washed with cold MeCN (60 mL), and sucked under house vacuum for 5 h to give 1 , 1 -Dimethylethyl 5-bromo-2,3-dihydro-1 H-indole-1 -carboxylate (ca 28.5 g prior to drying). LCMS (ES) m/z = 244, 242 as prominent fragments. 1 H NMR (400 MHz, DMSO-d6) ppm 1 .50 (s, 9 H), 3.06 (t, J=8.7 Hz, 2 H), 3.91 (t, J=8.7 Hz, 2 H), 7.31 (dd, J=8.5, 1.9 Hz, 1 H), 7.38 (s, 1 H), 7.51 – 7.71 (br s, 0.6 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromoindoline, and friends who are interested can also refer to it.

Reference:
Patent; GLAXOSMITHKLINE LLC; AXTEN, Jeffrey, Michael; GRANT, Seth, Wilson; HEERDING, Dirk, A.; MEDINA, Jesus, Raul; ROMERIL, Stuart, Paul; TANG, Jun; WO2011/119663; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem