Category: indolines-derivatives

Synthetic Route of 104618-31-7, 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. 104618-31-7, name is 2-(4-Hydroxycyclohexyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

4-[4-(1,3-Dioxo-1 , 3-dihydro-isoindol-2-yl)-cyclohexyloxy]-benzoic acid ethyl ester; To a stirred solution of 2-(4-hydroxycyclohexyl)isoindole-1 ,3-dione (8.0 g, 32.6 mmol) in dry THF (100 ml.) was added triphenyl phosphine (12.8 g, 48.8 mmol) and 4- hydroxy benzoic acid ethyl ester (5.44 g, 32.7 mmol). The reaction mixture was cooled to 0 0C and DIAD (9.6 g, 47.4 mmol) was added dropwise from an addition funnel over a period of 3 h. The reaction was gradually brought to room temperature and stirring continued for 3 h. The solvent was removed under vacuum and ether (100 ml.) was added and cooled to 0 0C. The solid formed was filtered and the clear filtrate concentrated and purified by column chromatography over neutral alumina (8 % AcOEt in hexane) to give 5.13 g (42 %) of 4-[4- (I .S-dioxo-I .S-dihydro-isoindol^-ylJ-cyclohexyloxyJ-benzoic acid ethyl ester. 1H-NMR (300 MHz, CDCI3); delta 1.24 – 1.36 (m, 2H), 1.40 (t, 3H), 1.63 – 1.77 (m, 3H), 2.19 – 2.29 (m, 2H), 2.62 – 2.79 (dq, 2H), 4.15 – 4.72 (m, 1 H), 4.35 (q, 2H), 7.01 (d, 2H), 7.71 (m, 2H), 7.82 (m, 2H), 8.0 (d, 2H). m/z: 394.1 (M+1 )+

The synthetic route of 2-(4-Hydroxycyclohexyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVO NORDISK A/S; WO2007/115935; (2007); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 6326-79-0, 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. 6326-79-0 name is 6-Bromoisatin, 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.

The mixture of IX-1 (6.5 g, 28.7 mmol), malonic acid (3.3 g, 31.7 mmol), NaOAc (2.95 g, 36 mmol) in AcOH (60 mL) were stirred at rt. After 6 hrs, NaOAc (2.95 g, 36 mmol) was added additional, then refluxed overnight. After cooling, the mixture was filtered and the filtrate was washed with water and EtOAc, then dried under reduced pressure to afford IX-2 (5 g, yield 66%) as a brown oil, which was used for next step directly.

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

Reference:
Patent; Buckman, Brad Owen; Nicholas, John Beamond; Emayan, Kumaraswamy; Seiwert, Scott D.; US2014/200215; (2014); A1;,
Indoline – Wikipedia,
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Reference of 2913-97-5,Some common heterocyclic compound, 2913-97-5, name is N-(2-Oxoethyl)phthalimide, molecular formula is C10H7NO3, 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.

Intermediate B3-2-(1,3-dioxoisoindolin-2-yl)acetaldehyde oxime A mixture of intermediate B2 (1.46g, 1equiv), hydroxylamine hydrochloride (0.64g, 1.2equiv), anhydrous K2CO3 (1.6g, 1.5equiv) in absolute methanol (10ml) was stirred at room temperature overnight. The solvent was evaporated under reduced pressure and the residue was diluted with water, extracted with dichloromethane three times. The organic phase was combined and washed with brine, dried and solvent evaporated to give the title compound as a white solid (0.75g). 1H-NMR (d6-DMSO, 400 MHz, ca 1:1 cis-trans isomer) delta4.30/4.37 (2x d, 2H, J=4.0), 6.81/7.35 (2x t, 1H, J=4.0), 7.81-7.88 (m, 4H), 10.86/11.34 (2x s, 1H); MS (EI) m/z: 204 (M+).

The synthetic route of 2913-97-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Institute of Materia Medica, Chinese Academy of Sciences; SHEN, Jianhua; WANG, Yiping; WANG, Kai; EP2725024; (2014); A1;,
Indoline – Wikipedia,
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Synthetic Route of 7477-63-6, 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. 7477-63-6 name is 7-Chloroisatin, 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.

0.4 mmol of 7-chloroisonin, 0.2 mmol of antipyrine, 0.04 mmol of imidazole and 1 mL of water were mixed, and the reaction was stirred under heating at 80 ° C for 48 hours.Then, the obtained reaction system was cooled to room temperature, extracted with dichloromethane, and the organic phase was collected. The obtained organic phase was dried over anhydrous sodium sulfate, concentrated, and separated by column chromatography (mobile phase: petroleum ether / ethyl acetate volume ratio) In the order of 4/1, 3/1, 2/1 and 1/1), the title compound I-11 (white solid, yield 77percent, purity 99.8percent) was obtained.

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

Reference:
Patent; Gannan Normal University; Zhang Yong; Nie Longjun; Liu Jinxiang; Fan Xiaolin; (23 pag.)CN110256407; (2019); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 100510-64-3, These common heterocyclic compound, 100510-64-3, name is 3,3-Dimethyl-6-nitroindolin-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.

A. 6-amino-3,3-dimethylindolin-2-one A mixture of 3,3-dimethyl-6-nitroindolin-2-one (1.2 g, 5.8 mmol) (Mertens et al, J. Med. Chem. 30:1279, 1987), 10% Pd-C (100 mg), and MeOH (100 mL) was stirred under hydrogen atmosphere (1 atm) for 10 h. The catalyst was filtered out and the filtrate was concentrated. The residue was purified by column to give an off-white solid (700 mg). MS: M+H=177. 1H NMR (d6-DMSO): 10.01 (s, 1H), 6.84 (d, 1H, J=8.0 Hz), 6.13-6.10 (m, 2H), 5.01 (s, 2H), 1.15 (s, 6H).

Statistics shows that 3,3-Dimethyl-6-nitroindolin-2-one is playing an increasingly important role. we look forward to future research findings about 100510-64-3.

Reference:
Patent; Kelly, Michael G.; Kincaid, John; Kaub, Carl J.; US2006/258689; (2006); 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. 205383-87-5, name is tert-Butyl 2-oxospiro[indoline-3,3′-pyrrolidine]-1′-carboxylate, A new synthetic method of this compound is introduced below., HPLC of Formula: C16H20N2O3

Tert-butyl 2-oxospiro[indoline-3,3?-pyrrolidine]-1?-carboxylate (1 g, 3.4 mmol) was added to a round bottom flask containing a stir bar and dissolved in acetonitrile (15 mL). Potassium carbonate (940 mg, 6.8 mmol) was added, followed by 4-bromo-1-(bromomethyl)-2-fluorobenzene (929 mg, 3.4 mmol). The mixture was stirred at room temperature overnight, and then evaporated under reduced pressure. The resulting residue was partitioned between water and ethyl acetate. The organic layer was collected, and the water layer was extracted with an additional ethyl acetate (2×50 mL). The organic layers were combined, dried over magnesium sulfate, and evaporated to afford a colorless solid, which was used directly in the next step. To a microwave vial containing a stir bar was added tert-butyl 1-(4-bromo-2-fluorobenzyl)-2-oxospiro[indoline-3,3?-pyrrolidine]-1?-carboxylate (457 mg, 0.96 mmol), followed by 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (200 mg, 0.96 mmol), cesium carbonate (626 mg, 1.9 mmol), 1,1?-bis(diphenylphosphino)ferrocene]-dichloropalladium (II) dichloromethane adduct (78 mg, 0.096 mmol), and the mixture was suspended in THF/water (4 mL, 1:1). The vial was sealed, and the mixture was heated to 160 C. for 10 min. The organic layer was removed, filtered through celite and evaporated to afford an oil, which was re-dissolved in excess TFA. This solution was allowed to stir at room temperature for 2 h, and then TFA was evaporated under reduced pressure. The resulting oil was used directly in the next step. 1-(2-fluoro-4-(1-methyl-1H-pyrazol-4-yl)benzyl)spiro[indoline-3,3?-pyrrolidin]-2-one (75 mg, 0.2 mmol) was added to a vial containing a stir bar and dissolved in DMF (1 mL). Potassium carbonate (41 mg, 0.3 mmol) was added, followed by iodomethane (15 muL, 0.2 mmol). The vial was sealed, and the mixture was stirred at room temperature for 2 h. The suspension was filtered to remove solids, and then purified using an SCX cartridge to afford the title compound as a clear oil. LCMS: RT=0.59 min, >99% (at) 254 nm, >99% (at) 215 nm; m/z (M+1)+=391. 1H NMR (400 MHz, CDCl3, delta (ppm)): 7.7 (s, 1H), 7.6 (s, 1H), 7.5 (dd, J=7.4, 0.6 Hz, 1H), 7.3-7.1 (m, 4H), 7.1-7.0 (m, 1H), 6.8 (d, J=7.8 Hz, 1H), 5.0 (s, 2H), 4.0 (s, 3H), 3.1-3.0 (m, 1H), 3.0-2.9 (m, 2H), 2.8-2.7 (m, 1H), 2.5 (s, 3H), 2.5-2.4 (m, 1H), 2.1 (dt, J=12.8, 7.7 Hz, 1H), HRMS calculated for C23H24N4OF (M+H)+ m/z: 391.1934, measured: 391.1933.

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; VANDERBILT UNIVERSITY; Lindsley, Craig W.; Conn, P. Jeffrey; Wood, Michael R.; Hopkins, Corey R.; Melancon, Bruce J.; Poslusney, Michael S.; US2013/123236; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 2058-74-4, name is 1-Methylisatin, 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 2058-74-4, Recommanded Product: 1-Methylisatin

General procedure: To a mixture of isatin (1 equiv.) and indole (1 or 2 equiv.) in water (3 mL), CuWO4 (10 mol%) was added and the mixture was stirred at room temperature for 2 h or heated at 60 C for 2 h. After completion of the reaction (monitoring by TLC), the mixture was cooled (in the case of bis-indolyl-2-oxindoles) and extracted with EtOAc (2×10 mL). The organic layers were washed with brine, dried using sodium sulfate. Evaporation of the solvent gave the desired product which was purified by silica gel column chromatography. Elution of the column with PE:EtOAc gave the desired products (5 or 6).

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:
Article; Paplal, Banoth; Sathish, Kota; Nagaraju, Sakkani; Kashinath, Dhurke; Catalysis Communications; vol. 135; (2020);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 611-09-6, 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. 611-09-6, name is 5-Nitroindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a mixture containing isatin derivatives (1 mmol),malononitrile or ethyl cynocette (1mmol) and 1,3-cyclldiketone (1 mmol) in water (5 mL), H-Fe3O4(at)DA-SO3H(0.01g) were added and stirred under reflux condition. The progress of the reaction was monitored by TLC (n-hexane:EtOAc 7:3). After completion of the reaction the mixture was cooled and the catalyst was separated by means of an external magnet from mixture, then the crude product was collected and washed with distilled water and dried. They were weighted for reporting of the yields.

The synthetic route of 5-Nitroindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mirhosseyni, Marzie Sadat; Nemati, Firouzeh; Elhampour, Ali; Combinatorial Chemistry and High Throughput Screening; vol. 21; 7; (2018); p. 487 – 494;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 112656-95-8, A common heterocyclic compound, 112656-95-8, name is 7-Nitroindoline-2,3-dione, molecular formula is C8H4N2O4, 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: Mg(ClO4)2 (10 mol %) was added to a mixture of isatin (2 mmol), malononitrile or ethyl cyanoacetate (2mmol), and dimedone (2 mmol) in aqueous ethanol solution(50%, v/v, 5 mL), and the resulting mixture was stirred at 50C for 30-60 min. Upon completion of the reaction (TLC),the mixture was allowed to cool to room temperature. The resulting solid was filtered and washed successively with water (2 × 30 mL) and cold aqueous ethanol (2 × 1 mL) to afford pure product 4.

The synthetic route of 112656-95-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wu, Chunlei; Shen, Runpu; Chen, Jianhui; Hu, Chunqi; Bulletin of the Korean Chemical Society; vol. 34; 8; (2013); p. 2431 – 2435;,
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. 16800-68-3, name is 1-Acetylindolin-3-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. category: indolines-derivatives

General procedure: To a solution of 1a (35 mg, 0.2 mmol) and 2a (52.4 mg,0.4 mmol) in DCE (3 mL) was added iodine (10 mg, 0.04 mmol). The reaction mixture was heated at 80 C for 24 h, then cooled to room temperature and quenched with saturated sodium thiosulfate. The mixture was extracted with CH2Cl2, the combined organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel to afford title compound.

The synthetic route of 16800-68-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Guo, Jing; Weng, Jiang; Huang, Gong-Bin; Huang, Lin-Jie; Chan, Albert S.C.; Lu, Gui; Tetrahedron Letters; vol. 57; 49; (2016); p. 5493 – 5496;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem