Category: indolines-derivatives

Related Products of 3891-07-4, A common heterocyclic compound, 3891-07-4, name is 2-(2-Hydroxyethyl)isoindoline-1,3-dione, molecular formula is C10H9NO3, 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.

Under nitrogen, to about 7.26g 38mmol N- (2- hydroxyethyl) phthalimide of THF solution was dropwise added 40mL has dropped to -10 C, contains about 2.28g 57mmol NaH in 15mL THF was added dropwise. After completing -10 C under stirring for 30min. Then 4.2mL containing about 36.2 In THF 15mL mmol 4- chloro-acetoacetate was slowly dropwise added to the above system, a solution of After completion, the reaction system was naturally warmed to room temperature and stirred overnight. Under ice-cooling, ethanol was added 4mL quenched Off the reaction, the reaction solution was slowly poured into 100mL 1mol / L hydrochloric acid and ice, the aqueous phase was extracted with ethyl acetate, The combined organic phase was washed with saturated sodium bicarbonate solution, washed successively with water, dried over anhydrous sodium sulfate, filtered, The solvent was removed rotary evaporation, and the residue was purified by column chromatography to give compound S815.93g, yield 54%

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; JiangsuSimcere Pharmaceutical Company, Ltd; JiangsuSimcere Pharmaceutical Research Co. Ltd.; Chen, Rong; Liu, Fei; Cong, Xin; Feng, Lin; Li, Haidao; Dong, Qingli; (62 pag.)CN102464608; (2016); B;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 84575-27-9, name is 7-Methoxyindoline-2,3-dione, molecular formula is C9H7NO3, 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. Quality Control of 7-Methoxyindoline-2,3-dione

To a suspension of 7-methoxyindoline-2,3-dione (1.0 g, 5.6 mmol) in AcOH (5.6 mL) was added bromine (0.35 mL, 6.7 mmol) at 0 C. The mixture was allowed to stir at rt for 2 h and was then poured into ice and stirred for 0.5 h. The resulting mixture was filtered and the solids were washed with H2O to afford the title compound as an orange solid (1.3 g, 92%). MS (ESI): mass calcd. for C9H6BrNO3, 256.0; m/z found, 257.6 [M+H]+. 1H NMR (400 MHz, DMSO-d6) delta 11.22 (s, 1H), 7.48 (d, J=1.7 Hz, 1H), 7.25 (dd, J=1.8, 0.7 Hz, 1H), 3.90 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 84575-27-9, its application will become more common.

Reference:
Patent; Janssen Pharmaceutica NV; Ameriks, Michael K.; Gyuris, Mario; Laforteza, Brian Ngo; Lebold, Terry Patrick; Meyer, Stephen Todd; Ravula, Suchitra; Savall, Brad M.; Shireman, Brock T.; Wade, Warren Stanfield; Gerencser, Janos; (87 pag.)US2018/111933; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 239463-85-5, A common heterocyclic compound, 239463-85-5, name is (R)-3-(5-(2-Aminopropyl)-7-cyanoindolin-1-yl)propyl benzoate (2R,3R)-2,3-dihydroxysuccinate, molecular formula is C26H31N3O8, 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.

40 g of 3-5-[(2R) -2-aminopropyl] -7-cyano-2,3-dihydro-1H-indol-1-yl propylbenzoate (2R, 3R) -tartrate,Acetonitrile 320 ml,20.6 g of anhydrous sodium carbonate, 26.9 g of 2- [2- (2,2,2-trifluoroethoxy) phenoxy] ethyl methanesulfonate was added and stirred under reflux for 24 hours.The reaction solution was cooled, filtered, concentrated under reduced pressure, and 400 ml of ethyl acetate and 320 ml of purified water were added to the concentrate, followed by stirring, separating the layers, and concentrating the organic layer under reduced pressure.To the concentrate, 240 ml of ethanol and 10.5 g of L-(+)-tartaric acid were added, stirred at room temperature for 5 hours, filtered and dried under reduced pressure to make 3-7-cyano-5-[(2R) -2- (2- [ 2- (2,2,2-trifluoroethoxy) phenoxy] ethyl amino) propyl] -2,3-dihydro-1H-indol-1-yl propylbenzoate (2R, 3R) -tartrate Obtained 45.1 g. (Yield 79.3%, ee value = 99.97% or more).

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; Ga Pi Bio Co., Ltd.; East F Ti L Co., Ltd.; Jeong Heon-seok; Kim Ryong-guk; (22 pag.)KR2020/4492; (2020); 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. 391-12-8, name is 7-(Trifluoromethyl)isatin, A new synthetic method of this compound is introduced below., Formula: C9H4F3NO2

The above product (163 mg, 0.654 mmol) was dissolved in 3.2 mL of dry dichloromethane, and Dess-Martin periodinane (290 mg, 0.68 mmol) was added to the solution at room temperature. After the reaction mixture was stirred for 30 min at the same temperature, saturated NaHCO3 aqueous solution was added. The mixture was extracted with ethyl acetate, and the extract was washed with brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo and the residue was purified by silica gel column chromatography (hexane/ethyl acetate = 95/5 to 75/25) to obtain the title compound as a white powder (140 mg, 86%).

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; Tokyo Institute of Technology; Kyoto University; EP2123637; (2009); 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 1074-82-4 as follows. Quality Control of Potassium 1,3-dioxoisoindolin-2-ide

REFERENCE EXAMPLE 13A Production of 4-(Diphenylmethoxy)-1-piperidinepentanamine 3.70 g of potassium phthalimide was dissolved in 20 ml of N,N-dimethylformamide; 5.4 ml of 1,5-dibromopentane was added, followed by stirring at room temperature for 15 hours. Ice water was added to the reaction mixture, followed by extraction with ethyl acetate; the extract was washed with saline, dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with hexane-ethyl acetate (4:1). The desired fraction was collected to yield 4.68 g of N-(5-bromopentyl)phthalimide as an oily substance.

According to the analysis of related databases, 1074-82-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US6627630; (2003); B1;,
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. 446292-08-6, name is (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Quality Control of (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione

2-({(5S) -2-oxo-3-[4- (3-oxo-4-morpholinyl) phenyl] -1,3-oxazolidin-5- yl} methyl)-1,3(2H) -dione (Formula 5) were added 75 ml of ethanol and 8.1 ml of a methylamine solution (concentration in water 40%) was added.The reaction mixture was then diluted with 60In Heating, Stir at this temperature for 2 hours.Confirm that the reaction is completed, and while maintaining the temperature, dilute the solution with 50 ml of ethanol and 3.04 ml of phosphoric acid, and slowly add the solution to the reaction solution. After confirming that the crystallization of the product was initiated and cooling to 20 C, the precipitated reaction product was filtered under suction. The resulting solid was dispersed in 110 ml of methanol, refluxed for 30 minutes and stirred, and then cooled to room temperature. The resulting crystals were filtered,And dried at 50 DEG C for 4 hours to obtain 11.1 g of morpholine diphosphate (Formula 2). (Yield: 96.0%)

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; IL DONG PHARMACEUTICAL CO., LTD.; LEE, Ki Yong; KWON, Jae Wook; SEO, Myeong Won; KANG, Jae Hoon; (15 pag.)KR2017/98031; (2017); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 2058-72-2, A common heterocyclic compound, 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, molecular formula is C9H6BrNO2, 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 ligand 1(11mol %) in ethanol (2 ml) was added coppersalt (10 % mol), After 5 hours the color of the solution changed from blue-green to purple. Then,dipolarophile (0.20 mmol) has been added andstirred about 30 min. Next, a mixture of isatin derivatives (0.20 mmol) and (S)-proline (0.21 mmol), in 3 ml ethanol/dichloromethane (5/1) was added to reaction mixture.After completion of the reaction (monitored by TLC), reaction was diluted withdiethyl ether and filtered through a pad of silica gel. The organic layer wasconcentrated in vacuum to furnish the products, which were recrystallized fromethanol.

The synthetic route of 2058-72-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Salahi, Farbod; Taghizadeh, Mohammad Javad; Arvinnezhad, Hamid; Moemeni, Mehdi; Jadidi, Khosrow; Notash, Behrouz; Tetrahedron Letters; vol. 55; 9; (2014); p. 1515 – 1518;,
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. 2436-29-5, name is 3-(1,3-Dioxoisoindolin-2-yl)propanal, A new synthetic method of this compound is introduced below., HPLC of Formula: C11H9NO3

General procedure: Neat TiCl4 (120 muL, 1.1 mmol) was added dropwise to a solution of the corresponding alpha-silyloxy methyl ketone (1.0 mmol) in CH2Cl2 (5.0 mL) at -94 C, and the mixture was stirred for 5 min. Then, anhydrous i-Pr2NEt (190 muL, 1.1 mmol) was added dropwise and the resulting dark red solution was stirred for 30 min at -94 C. After dropwise addition of the freshly distilled aldehyde (1.5 mmol), stirring was continued for 30 min at -78 C. The reaction was quenched by the addition of saturated NH4Cl (5 mL) and vigorously stirred at room temperature for 10 min. Then it was diluted with Et2O (50 mL), and washed with H2O (50 mL), saturated NaHCO3 (50 mL) and brine (50 mL). The combined organic extracts were dried (MgSO4) and concentrated. The resulting crude was analysed by 1H NMR and purified by column chromatography.

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:
Article; Lorente, Adriana; Pellicena, Miquel; Romea, Pedro; Urpi, Felix; Tetrahedron; vol. 71; 7; (2015); p. 1023 – 1035;,
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. 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Safety of 5-Bromo-1-methylindoline-2,3-dione

General procedure: A mixture of an N-substituted isatin (1.0 mmol), benzoyl cyanid (0.145 g, 1.1 mmol), and MS 4A (200 mg) in dry acetonitrile (2 mL) was stirred at room temperature for the indicated time (Table 2). The progress of the reaction was monitored by TLC. After completion of the reaction, the MS 4A was recovered by simple filtration, thoroughly washed with dry acetonitrile. Then the filtrate was evaporated to dryness in a rotary evaporator under reduced pressure and the residue was crystallized from a mixture of CH2Cl2 and petroleum ether, which yielded the pure products.

The synthetic route of 2058-72-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Esmaeili, Abbas Ali; Ghalandarabad, Saeid Amini; Zangouei, Mahdieh; Tetrahedron Letters; vol. 53; 42; (2012); p. 5605 – 5607;,
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. 25369-33-9, name is 7-Chloroindolin-2-one, A new synthetic method of this compound is introduced below., name: 7-Chloroindolin-2-one

To a coo?ed (0 C) soution of 7-choroindohn-2-one (1 g, 6.0 mmo) in TFA (11 mL) was added Nbromosuccinimide (1 g, 6.0 mmo) portion wise and stirred the mixture at same temperature for 6 h. Concentrated TFA in vacuo with DCM (25 mL) and then with EtOAc. The crude product was triturated with ethano to provide the tiDe compound as a white soid (861 mg, 58% yie?d). MS (ES):mass cacd, for C6H5BrCNO, 244.9; m/z found, 246.0 [M+H]. 1H NMR (500 MHz, DMSO d6) oe 10.92 (5, 1 H), 7.52 7.48 (m, I H), 7.38 (d, J = 1.2 Hz, I H), 3.62 (s, 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; JANSSEN PHARMACEUTICA NV; AMERIKS, Michael K.; RAVULA, Suchitra; SAVALL, Bradley M.; SWANSON, Devin M.; ZIFF, Jeannie M.; SHIREMAN, Brock T.; (167 pag.)WO2016/176463; (2016); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem