Month: August 2021

Electric Literature of 20870-90-0, These common heterocyclic compound, 20870-90-0, name is 5-Bromo-1-methyl-2-oxoindoline, 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 precooled stirring suspension of NaH (6.0 mmol, 0.144 g) in THF (10 mL) at -78 C was added a solution of N-methyloxindole (5a) (6.0 mmol, 0.883 g) in THF (10 mL) dropwise. Then the cooling bath was removed and stirring continued for 5 min (till the formation of clear solution). Then the reaction mixture was again cooled to -78 C and a solution of methyl 3-hydroxy-2-methylene-3-phenylpropanoate (6a) (2.0 mmol, 0.468 g) in THF (15 mL) was added dropwise over 30 min. After stirring for further 10 min at the same temperature, the cooling bath was removed and the reaction was quenched with saturated NH4Cl solution and extracted with EtOAc (3×30 mL). Combined organic layer was dried over anhydrous Na2SO4.. Solvent was removed and the crude obtained was purified by column chromatography(10-15% EtOAc in hexanes) provided title compound (7a) (0.539 g) as a colorless solid in 84% yield.

Statistics shows that 5-Bromo-1-methyl-2-oxoindoline is playing an increasingly important role. we look forward to future research findings about 20870-90-0.

Reference:
Article; Basavaiah, Deevi; Lingam, Harathi; Babu, Thelagathoti Hari; Tetrahedron; vol. 74; 19; (2018); p. 2306 – 2313;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 1035235-27-8, These common heterocyclic compound, 1035235-27-8, name is tert-Butyl 4-bromoisoindoline-2-carboxylate, 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.

Step f. Bis(pinacolato)diboron (87.5 g, 344 mmol) was added to a solution of tert-butyl 4- bromoisoindoline-2-carboxylate (85.6 g, 287 mmol) in 1,4-dioxane (850 ml), followed by potassium acetate (56.2 g, 574 mmol), and the resulting mixture was degassed with nitrogen for 15 min. Pd(dppf)Cl2 (21 g, 28.7 mmol) was added to the reaction flask and the resulting mixture was heated at 100C for 6 h. Upon completion of the reaction, as determined by LCMS, the mixture was cooled to rt and filtered through a pad of Celite, washing with EtOAc (2 chi 50 ml). The filtrate was evaporated to dryness under vacuum to give a black oily residue, which was dissolved in DCM and passed through a silica pad, eluting with DCM. The solvent was subsequently removed under vacuum to give a solid, which was triturated with hexane (200 ml) and dried under vacuum at rt to give the desired product as a white solid (88 g, 89%). LCMS (Method R): rt 3.36 min, m/z 346, 290 (-iBu), 246 (-Boc) [M+H]+; NMR (400 MHz, DMSO-d6) delta ppm 7.62-7.54 (m, 1H), 7.48-7.41 (m, 1H), 7.33-7.25 (m, 1H), 4.70-4.62 (m, 2H), 4.60-4.53 (m, 2H), 1.49-1.43 (m, 9 H), 1.33-1.27 (m, 12 H).

The synthetic route of 1035235-27-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MISSION THERAPEUTICS LIMITED; GIBSON, Karl Richard; JONES, Alison; KEMP, Mark Ian; MADIN, Andrew; STOCKLEY, Martin Lee; WHITLOCK, Gavin Alistair; WOODROW, Michael D; (241 pag.)WO2017/158388; (2017); 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. 150544-04-0, name is 6-Aminoindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 150544-04-0

To 6-aminoindolin-2-one (30 mg, 0.202 mmol) in THF (1 mL) was added acetic anhydride (19 uL, 0.202 mmol). After 2 hrs the product was precipitated with ether, filtered and dried to give 25 mg, 66percent of a white solid. 1H NMR (400 MHz, CD3OD) delta 7.41 (s, IH), 7.16 (d, J = 7.0 Hz, IH), 7.00 (d, J = 8.0 Hz, IH), 3.49 (s, 2H), 2.12 (s, 3H); MS ESI 191.0 [M + H]+, calcd for [C10H10N2O2 + H]+ 191.08.

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 150544-04-0.

Reference:
Patent; UNIVERSITY HEALTH NETWORK; WO2009/79767; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 39603-24-2, A common heterocyclic compound, 39603-24-2, name is 5,7-Dimethylindoline-2,3-dione, molecular formula is C10H9NO2, 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 asolution of isatin 3 (1.0mmol), 2-aminopyridine 2 (1.35mmol)andisocyanide 4 (1.35mmol) in 4mL of n-butyl alcohol was added HClO4 (1.0mmol), and the reaction mixture was stirred under refluxfor 8 h. After cooling to room temperature, the precipitate was collected by filtration, rinsed with ethanol and dried to afford the target compound 1.

The synthetic route of 39603-24-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yang, Bo; Tao, Chuanye; Shao, Taofeng; Gong, Jianxian; Che, Chao; Beilstein Journal of Organic Chemistry; vol. 12; (2016); p. 1487 – 1492;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 7477-63-6, 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. 7477-63-6, name is 7-Chloroisatin, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Isatins (1a?j, 3.0 g), hydrazine hydrate (80percent, 13 mL) and water (13 mL) were added to a flask equipped with a thermometer with vigorous stirring. The reaction mixture was kept at 140 °C in an oil bath for 6 h before being cooled to r.t., when hydrochloric acid (2.0 mol L?1) was added to bring the pH to pH 2. The reaction mixture was stirred at r.t. for 12 h. Compounds 2a?j were obtained by filtering under vacuum and recrystallisation from absolute ethanol.

The chemical industry reduces the impact on the environment during synthesis 7-Chloroisatin. I believe this compound will play a more active role in future production and life.

Reference:
Article; Zhang, Chao; Xu, Juan; Zhao, Xinyu; Kang, Congmin; Journal of Chemical Research; vol. 41; 9; (2017); p. 537 – 540;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 2058-72-2, name is 5-Bromo-1-methylindoline-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 2058-72-2, category: indolines-derivatives

A stirred brown solution of 5-bromo-1-methylindoline-2,3-dione (500 mg, 2.083 mmol) in DCM (10 ml.) was cooled down to 0C and bis(2-methoxyethyl)aminosulfur trifluoride (1.152 ml, 3.12 mmol) was slowly added into it, followed by EtOH (0.036 ml_, 0.625 mmol). The reaction mixture was allowed to warm up and stir overnight at RT. Bis(2-methoxyethyl)aminosulfur trifluoride (1.152 ml_, 3.12 mmol) was added and the mixture was stirred 8 hr at RT. The reaction was quenched with saturated aqueous Na2C03 solution and both phases were separated. The organic layer was washed with brine, dried over MgS04, filtered and concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel (Cyclohexane / 0 to 50% EtOAc). The resulting solid was diluted with MeOH (2 ml_), sonicated, cooled down to 0C and filtrated off to afford the title product (183 mg, 0.698 mmol) as a beige solid. Rt = 1.07 min (UPLC- MS); 1H NMR (400 MHz, DMSO-d6) d ppm 3.17 (s, 3 H) 7.22 (d, J=8.44 Hz, 1 H) 7.84 (d, J=8.44 Hz, 1 H) 8.01 (s, 1 H).

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; NOVARTIS AG; ARISTA, Luca; CHAMOIN, Sylvie; D’ALESSANDRO, Pier Luca; LINDVALL, Mika; LIZOS, Dimitrios; STIEFL, Nikolaus Johannes; TEIXEIRA-FOUCHARD, Sylvie; ULLRICH, Thomas; WEILER, Sven; (151 pag.)WO2019/102256; (2019); 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. 19727-83-4, name is 6-Nitroindoline, A new synthetic method of this compound is introduced below., Product Details of 19727-83-4

The tert-butyl 6-aminoindoline-l-carboxylate used as a starting material was prepared as follows :-Di-tert-butyl dicarbonate (7.2 g) was added to a mixture of 6-nitroindoline (4.92 g) and methylene chloride (50 ml) and the mixture was stirred at ambient temperature for 1 hour. 4-Dimethylaminopyridine (0.37 g) was added and the reaction mixture was stirred at ambient temperature for 16 hours. The resultant mixture was evaporated and the residue was purified by column chromatography on silica using increasingly polar mixtures of petroleum ether (b.p. 40-60C) and ethyl acetate as eluent. There was thus obtained tert-butyl 6-nitroindoline- 1-carboxylate as a solid (5.45 g); 1H NMR: (CDCl3) 1.6 (s, 9H), 3.2 (t, 2H), 4.1 (t, 2H), 7.2 (d, IH), 7.85 (d, IH), 8.3 (br s, 0.5H), 8.7 (br s, 0.5H).

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; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/99317; (2007); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 320734-35-8, name is 7-Bromooxindole, 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 320734-35-8, HPLC of Formula: C8H6BrNO

To a solution of 7-bromo-l ,3-dihydro-2H-indol-2-one (200 mg, 0.94 mmol) in DMF (5 mL) were added cesium carbonate (676 mg, 2.07 mmol) and iodomethane (294 mg, 2.07 mmol). The reaction mixture was stirred at ambient temperature for 18 h, then partitioned between H2O (50 mL) and EtOAc (100 mL). The organic extract was dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of hexane: EtOAc – 100:0 to 85: 15, to give the title compound. MS: m/z = 254 (M + 1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 7-Bromooxindole, and friends who are interested can also refer to it.

Reference:
Patent; MERCK & CO., INC.; WO2006/31513; (2006); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 954-81-4, 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. 954-81-4 name is N-(5-Bromopentyl)phthalimide, 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.

General procedure: To a stirred suspension of phenol (12 mmol) and K2CO3 (20 mmol) in DMF (20 mL), intermediates 2a-2e (10 mmol) were added. After stirred at room temperature for 10-12 h, the mixture was quenched with water and extracted with EtOAc for three times. The combined organic phase was dried over MgSO4, filtered and concentrated to give the crude product, which was puried by chromatography on an silica gel column (EtOAc/petroleum ether as eluent) to give the products. The preparation of compounds 3a-3e was according to the method previously described [42].

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

Reference:
Article; Shan, Wen-Jun; Huang, Ling; Zhou, Qi; Meng, Fan-Chao; Li, Xing-Shu; European Journal of Medicinal Chemistry; vol. 46; 12; (2011); p. 5885 – 5893;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application 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: Indole-2,3-dione 1 (1 mmol) and 1,2-diamine 2 (1 mmol) and 5 mol% of Cu doped CdS NPs in ethylene glycol (10 ml) was introduced in a 50 ml round-bottomed flask. The flask was placed in the microwave cavity and subjected to irradiation for appropriate time at 80 C using a maximum power of 300 W. When the reaction was complete, the reaction mixture was extracted with ethylacetate; the organic layer was removed under reduced pressure to afford the crude product. The pure products were obtained by crystallization from ethanol.

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, 5,7-Dimethylindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Dandia, Anshu; Parewa, Vijay; Maheshwari, Shuchi; Rathore, Kuldeep S.; Journal of Molecular Catalysis A: Chemical; vol. 394; (2014); p. 244 – 252;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem