Author: Jessica.F

Adding a certain compound to certain chemical reactions, such as: 20870-78-4, name is 5-Bromoindolin-2-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 20870-78-4, category: indolines-derivatives

[0409] A mixture of an appropriately substituted oxindole, an appropriately substituted aldehyde (1 equivalent) and piperidine (excess) in ethanol (0.2M) was stirred at between room temperature to 100 C. After completion, the mixture was concentrated and then triturated with dil. HCl solution. The resulted precipitate was collected by vacuum filtration, washed with water and dried to give the desired product 5-Phenyloxindole (synthesised from 5-bromooxindole and phenyl boronic acid [Aldrich] via Suzuki coupling) was condensed with 3-(4-benzensulfonyl-2-formyl-5-methyl-1H-pyrrol-3-yl)-propionic acid (prepared as described above in the synthesis of aldehyde 2) and piperidine in ethanol to give the titled compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromoindolin-2-one, and friends who are interested can also refer to it.

Reference:
Patent; Sugen, Inc.; US2005/32871; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 56341-37-8, name is 6-Chlorooxindole, 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 56341-37-8, SDS of cas: 56341-37-8

Step 1: Synthesis of 2.6-dichloro-1H-indole (2):1003131 To a stirred solution of 6-chloroindolin-2-one 1(500 mg, 2.99 mmol) in toluene (25 mL) under inert atmosphere were added N,N-dimethylaniline (362 mg, 2.99 mmol) and POC13 (918 g, 5.98 mmol) at RT; heated to 110 C and stirred for 1 h. The reaction was monitored by TLC; after completion of the reaction, the reaction mixture was quenched with 10% aq. NaHCO3 solution (30 mL) and extracted with EtOAc (2 x 30 mL). The combined organic extracts were dried over Na2SO4, filtered and concentrated under reduced pressure to obtain the crude. This was purified by silica gel column chromatography using 5% EtOAc/ Hexanes to afford compound 2 (350 mg, 63%) as an off-white solid. 1H NMR (400 MHz, CDC13): 5 8.09 (br s, 1H), 7.41 (d, J= 8.4 Hz, 1H), 7.28 (s, 1H), 7.09 (d, J= 8.4 Hz, 1H), 6.39 (s, 1H); MS (ES): m/z184 (M – Hj

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

Reference:
Patent; PHARMAKEA, INC.; HUTCHINSON, John, Edward; LONERGAN, David; WO2015/77503; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 169037-23-4, These common heterocyclic compound, 169037-23-4, name is 5-(Trifluoromethoxy)indoline-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.

General procedure: The mixture of isatin 1 (29.4 mg, 0.2 mmol), antipyrine 2a (84.7 mg, 0.45 mmol) in 1mL H2O were stirred at 120 . Once the reaction completed (indicated by colorchange from red to white), the mixture was then cooled down to the room temperature.The insoluable solid mixture was filtered, washed by water and dried under vacuum to afford the desired product 4a in high pure form.

The synthetic route of 169037-23-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Yong; Nie, Long-Jun; Luo, Liang; Mao, Jia-Xin; Liu, Jin-Xiang; Xu, Guo-Hai; Chen, Deliang; Luo, Hai-Qing; Tetrahedron; vol. 76; 7; (2020);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 101207-45-8, A common heterocyclic compound, 101207-45-8, name is 2-(4-Methylbenzyl)isoindoline-1,3-dione, molecular formula is C16H13NO2, 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.

Synthesis Intermediate 4 Dissolve 12.3g of 2-(4-methylbenzyl)-1H-isoindole-1,3-dione in chloroform, then add 8.7g of chlorosulfonic acid, Reaction at 80C for 3h; after the reaction, After washing with water and removing the solvent, 15.75 g of Intermediate 4 was obtained with a yield of 95%.

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; Zhengzhou Shouxing Pharmaceutical Institute Co., Ltd.; Deng Zhaoxi; (11 pag.)CN110627706; (2019); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 6341-92-0, These common heterocyclic compound, 6341-92-0, name is 6-Chloroisatin, 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: Substituted isatin (10 mmol) was dissolved in hydrazine hydrate (98%, 10 mL, 32.5 mmol) and refluxed for 15-30 min (130 C). The reaction mixture was then poured into cold water, extracted withethyl acetate. The organic layer was then dried over sodium sulfate. Evaporation of the solvent and recrystallization from hexane/ethylacetate provided the substituted oxindole.

Statistics shows that 6-Chloroisatin is playing an increasingly important role. we look forward to future research findings about 6341-92-0.

Reference:
Article; Zhang, Lidan; Ren, Wen; Wang, Xiaoyan; Zhang, Jiaying; Liu, Jie; Zhao, Lifeng; Zhang, Xia; European Journal of Medicinal Chemistry; vol. 126; (2017); p. 1071 – 1082;,
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 20870-90-0 as follows. Quality Control of 5-Bromo-1-methyl-2-oxoindoline

A mixture of 5-bromo-1-methyl-1,3-dihydro-2H-indol-2-one (Maybridge, cat No.CC63010, 0.30 g, 1.3 mmol), 4,4,5,5,4′,4′,5′,5′-octamethyl-[2,2′]bi[[1,3,2]dioxaborolanyl](500 mg, 2.0 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complexed with dichloromethane (1:1) (50 mg, 0.07 mmol) and potassium acetate (390 mg, 4.0 mmol) in 1,4-dioxane (10 mL) was purged with nitrogen and heated at 90 C. overnight. After cooling it was concentrated. The crude material was purified by flash chromatography on a silica gel column eluting with 0 to 25% EtOAc in hexanes to give the desired product. LC-MS calculated for C15H21BNO3 (M+H)+: m/z=274.2. found 274.1.

According to the analysis of related databases, 20870-90-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Incyte Corporation; Wu, Liangxing; Courter, Joel R.; He, Chunhong; Li, Jingwei; Lu, Liang; Sun, Yaping; Wang, Xiaozhao; Yao, Wenqing; Zhang, Colin; Zhuo, Jincong; (87 pag.)US2016/9720; (2016); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 446292-08-6, These common heterocyclic compound, 446292-08-6, name is (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-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.

50 g (0.1 10 mol) of 2-({(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-1 ,3-oxazolidin-5- yl}methyl)-1 H-isoindole-1 ,3(2H)-dione (II), 45.81 mL of methylamine (40% aqueous solution, 0.53 mol) and 1250 mL of methanol were charged in a 3 L flask and the reaction mixture was heated to 65 C for 1 hour. Afterwards, 77.81 g (0.610 mol) of oxalic acid dihydrate in 233 mL of methanol were added dropwise until pH 2-3 was reached, at which the solid started to precipitate, and heated the reaction mass to reflux for 1 hour. After cooling to 25 C for 1 h, the product was filtered off, washed with methanol and dried under vacuum at 50 C.Yield: 37 g. Molar yield: 82.22%. HPLC purity: 99.91 %. M.P.: 195.90 C (DSC).

The synthetic route of 446292-08-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LABORATORIOS LESVI, S. L.; VISHNU NEWADKAR, Ravindranath; CHANGDEO GAIKWAD, Avinash; MADHUKAR HARAD, Ajay; DALMASES BARJOAN, Pere; WO2013/53739; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 1074-82-4, These common heterocyclic compound, 1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide, 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: To a solution of potassium 1,3-dioxoisoindolin-2-ide (1.85 g, 10.0 mmol), potassium iodide (0.08 g, 0.5 mmol) in acetone (25.0 mL), 1,2-dibromoethane dissolved in acetone (5.0 mL) was added by dropping funnel (3.72 g, 20.0 mmol), refluxed for 10 h. Monitored by TLC, and then filtered, concentrated by vacuum. The crude compound was purified by column chromatography on silica gel to give the desired intermediate 4 2-(2-bromoethyl) isoindoline-1,3-dione (1.83 g, 72.5% yield) as a white solid.

Statistics shows that Potassium 1,3-dioxoisoindolin-2-ide is playing an increasingly important role. we look forward to future research findings about 1074-82-4.

Reference:
Article; Xie, Ruliang; Mei, Xiangdong; Ning, Jun; Chemical and Pharmaceutical Bulletin; vol. 67; 4; (2019); p. 345 – 350;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 20870-79-5, 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 20870-79-5 as follows.

To a solution of 5-nitro-oxindole (25 g) in 120 mL of dimethylacetamide in a Parr bottle was added 10% Pd/C (0.5 g). The mixture was hydrogenated (40 psi H2) for 16 hours. The catalyst was removed by filtration and the filtrate was diluted with ether (2 L) to provide 5-amino-oxindole (10.5 g; 50%).

According to the analysis of related databases, 20870-79-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pfizer Inc; US2005/256144; (2005); 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. 17630-75-0, name is 5-Chloro-2-oxindole, A new synthetic method of this compound is introduced below., Product Details of 17630-75-0

A 5 mL of ethanol solution containing 5-chlorooxindole (167 mg, 1 mmol), 2- pyridine-carboxaldehyde (129 mg, 1.2 mmol) and 3 drops of piperidine was stirred at 80C for 6 hours. After cooling the solution to 5C, yellow precipitate was obtained (200 mg, 78%). MS: TITLE 257 [M+1] +.

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; IRM LLC; THE SCRIPPS RESEARCH INSTITUTE; WO2004/37247; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem