Category: indolines-derivatives

Some common heterocyclic compound, 87-48-9, name is 5-Bromoindoline-2,3-dione, molecular formula is C8H4BrNO2, 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. category: indolines-derivatives

General procedure: Isatin derivatives 1a-c (0.005 mol) were stirred in acetonitrile(20 mL) with (0.007 mol) of the appropriate methyl iodide 2, propyliodide 3 or benzyl bromide 7a-d in the presence of catalytic amountof potassium iodide with (0.010 mol) of dry potassium carbonate atreflux temperature. The reaction was monitored with TLC. Aftercomplete of reaction, the mixture was poured into ice-water, theformed solid was collected, washed with water and recrystallizedfrom ethanol-water to furnish the final compounds 4a-f and 8a-l[58-61].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 87-48-9, its application will become more common.

Reference:
Article; Eldehna, Wagdy M.; Abo-Ashour, Mahmoud F.; Nocentini, Alessio; El-Haggar, Radwan S.; Bua, Silvia; Bonardi, Alessandro; Al-Rashood, Sara T.; Hassan, Ghada S.; Gratteri, Paola; Abdel-Aziz, Hatem A.; Supuran, Claudiu T.; European Journal of Medicinal Chemistry; vol. 162; (2019); p. 147 – 160;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 118289-55-7, A common heterocyclic compound, 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one, molecular formula is C10H9Cl2NO, 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.

Example 5 Preparation of 5- [2- [4- (1, 2- benzisothiazol-3-yl) -1-piperazinyl] ethyl] -6-chloro-1, 3-dihydro-2H-indol-2-one (Ziprasidone base) Example 2 was repeated with the exception that 10 ml of 1-butyl-3-methylimidazolium bromide was used instead of 8 ml of 1-ethyl-3-methylimidazolium methyl sulfate. After the completion of the reaction the presence of 5- [2- [4- (1, 2- benzisothiazol-3-yl) -1-piperazinyl] ethyl] -6-chloro-1, 3- dihydro-2H-indol-2-one was confirmed by HPLC.

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; KRKA; EP1889844; (2008); A2;,
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 22190-33-6 as follows. Product Details of 22190-33-6

REFERENCE EXAMPLE 8 1-boc-5-Bromoindoline 5-bromoindoline (10 g) was added in one portion to molten Boc-anhydride (11.6 g) at 30-40 C. Immediate effervescence was followed by the formation of a solid cake which was triturated with pentane to give the title compound (15 g) as a white powder.

According to the analysis of related databases, 22190-33-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Aventis Pharma Ltd.; Aventis Recherche Developpment; US6608084; (2003); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 59-48-3,Some common heterocyclic compound, 59-48-3, name is Indolin-2-one, molecular formula is C8H7NO, 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.

PREPARATION H 5-Acetyloxindole The titled compound was prepared by reaction of oxindole with acetyl chloride and aluminum chloride in carbon disulfide.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Indolin-2-one, its application will become more common.

Reference:
Patent; Pfizer Inc.; US4678802; (1987); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 3676-85-5,Some common heterocyclic compound, 3676-85-5, name is 5-Aminoisoindoline-1,3-dione, molecular formula is C8H6N2O2, 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.

Potassium hydroxide (0.415 g, 7.4 mmol) was added to a solution of 4-aminophthalimide (35) (1.00 g, 6.17 mmol) in dimethylformamide (50 ml) and the mixture was stirred at ambient temperature. After 2 hours, 4-trifluoromethylbenzylbromide (36) (1.9 mL, 12.34 mmol) was further added to the mixture and the mixture was stirred for another 18 hours. Water (100 ml) and ethyl acetate (100 ml) was added and the resulting phases separated. The organic phase was washed with brine, dried over sodium sulfate and concentrated in vacuum. Purification by chromatography on silica gel (Gradient: 0-50 % ethyl acetate in cyclohexane) afforded Compound 37 as a yellow solid (0.750 g, 38 % yield): Rf= 0.2 (hexane/ethyl acetate 2:1 v/v). The Compound 37 (0.20g, 0.62 mmol.) was dissolved in dichloromethane (5 ml) and purged with argon. Benzyl chloroformate (0. lmL, 0.74 mmol) and triethylamine (0.60 mmol) were added to the amine solution and the resulting mixture was stirred for 2 hours at ambient temperature. After removal of the dichloromethane in vacuum, ethyl acetate (20 ml) and 10 % citric acid (20 ml) were added thereto and the resulting phases were separated. The organic phase was washed with 10 % sodium bicarbonate (20 ml) and brine (20 ml), dried over sodium sulfate and concentrated in vacuum. The residue was purified by chromatography on silica gel, and the resulting product was Compound 38. Compound 38,

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Aminoisoindoline-1,3-dione, its application will become more common.

Reference:
Patent; TAIWANJ PHARMACEUTICALS CO., LTD.; YANG, Syaulan S.; LEE, Kuang Yuan; LIU, Meng Hsien; JIANG, Yan-Feng; FAN, Yu-Shiou; CHEN, Chi-Han; LIU, Sheng Hung; (94 pag.)WO2019/51222; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 20870-79-5, These common heterocyclic compound, 20870-79-5, name is 5-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.

General procedure: Appropriate indolin-2-one or indoline-2-thione (0.3 g) was mixed with acetic anhydride (3 mL) and 4-dimethylaminopyridine (DMAP, 1 mol %). The mixture was heated at 150 C in a round-bottomed flask equipped with an air condenser and CaCl2 guard tube. The reaction time for each reactant is provided in [Table 2] and [Table 3]. After the completion of the reaction excess acetic anhydride was evaporated under reduced pressure. The solid residue obtained in the case of the triacetylated products was suspended in cold methanol and vacuum filtered. The product collected was thoroughly washed with hexane and dried. In the case of mono and diacetylated products the solid residue was purified using flash column chromatography (FCC) (silica gel, hexanes/ethyl acetate).

Statistics shows that 5-Nitroindolin-2-one is playing an increasingly important role. we look forward to future research findings about 20870-79-5.

Reference:
Article; Jha, Mukund; Chou, Ting-Yi; Blunt, Brian; Tetrahedron; vol. 67; 5; (2011); p. 982 – 989;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 32692-19-6, name is 5-Nitroindoline, 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 32692-19-6, category: indolines-derivatives

To a solution of 300mg (1.83mmol) of 5-nitroindoline in 20mL of dichloromethane were added 141muL (2.74mmol) of methanesulfonyl chloride and 382muL (2.74mmol) of triethylamine, and the mixture was stirred for 2 hours at room temperature. 141muL (2.74mmol) of methanesulfonyl chloride and 255muL (1.83mmol) of triethylamine were further added to the reaction mixture, and the mixture was stirred for 2 hours at room temperature. Then, water was added to the reaction mixture and the mixture was extracted with dichloromethane. The organic layer was washed with saturated saline solution and dried over with anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was treated with diethyl ether, then, the precipitates were collected by filtration to give 410mg (92%) of the title compound.

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

Reference:
Patent; Daiichi Asubio Pharma Co., Ltd.; EP1775298; (2007); 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. 4403-36-5, name is 2-(1,3-Dioxoisoindolin-2-yl)ethanesulfonylchloride, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 2-(1,3-Dioxoisoindolin-2-yl)ethanesulfonylchloride

Bis(4-methoxybenzyl)amine (900 mg) was dissolved in dichloromethane (20 ml) and cooled to 0C. To this solution, triethylamine (1.02 ml) was added and compound 49 (1.05 g) was added in small portions, followed by stirring at room temperature for 3 hours. After addition of water, the reaction mixture was extracted with dichloromethane. The organic layer was washed with brine and dried over magnesium sulfate. After filtration and evaporation of the solvent under reduced pressure, the resulting residue was purified by silica gel column chromatography (developing solvent: ethyl acetate:n-hexane 1:1 to ethyl acetate) to give the desired compound (compound 50) (1.4 g, yield 81%). 1H-NMR (300MHz, CDCl3) delta: 3.24(2H, t, J=6.8Hz), 3.81(6H, s), 4.10-4.14(2H, m), 4.29(4H, s), 6.88(4H, d, J=8.7Hz), 7.23(4H, d, J=8.7Hz), 7.73(2H, dd, J=3.1, 5.3Hz), 7.87(2H, dd, J=3.1, 5.3Hz). Rf value (silica gel plate, developing solvent: ethyl acetate:n-hexane = 1:1): 0.24.

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 4403-36-5.

Reference:
Patent; CHUGAI SEIYAKU KABUSHIKI KAISHA; EP1634874; (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. 14192-26-8, name is Methyl 2-oxoindoline-6-carboxylate, A new synthetic method of this compound is introduced below., Product Details of 14192-26-8

a) Methyl 3,3-dimethyl-2-oxoindoiln-6-carboxylate To a solution of Mel (7.42 g, 3.27 ml, 52.3 mmol) in DMF (75.0 ml) was added methyl 2- oxoindoline-6-carboxylate (5 g, 26.2 mmol). Once everything was disolved NaH (60 % in mineral oil, 1.05 g, 26.2 mmol) was added and the reaction mixture was stirred for 30 minutes at room temperature. Then again NaH (60 % on mineral oil, 523 mg, 13.1 mmol) was added and stirring was continued for another hour. Again NaH (60 % on mineral oil, 523 mg, 13.1 mmol)was added and stuffing was continued for 15 hours. The reaction was quenched with 1 M aqueous HC1 solution, the mixture was extracted with ethyl acetate and the organic layers were washed with water. The combined organic layers were dried with sodium sulfate, filtered and the obtained solution was concentrated in vacuo. The resulting solid was triturated with diisopropylether, filtered and the collected solid was dried. The title compound was obtained as red solid(4.61 g)MS ESI (m/z): 220.3 [(M+H)i.1H NMR (CDC13, 300 MHz): oe = 7.98 (br s, 1H), 7.78 (dd, J=1.3, 7.8 Hz, 1H), 7.58 (d, J=1.0 Hz,1H), 7.26 (d, J=7.7 Hz, 1H), 3.92 (s, 3H), 1.42 (s, 6H).

The synthetic route of 14192-26-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BRUNNER, Daniela; HILPERT, Hans; KOLCZEWSKI, Sabine; LIMBERG, Anja; MALBERG, Jessica; PRINSSEN, Eric; RIEMER, Claus; SHANKAR, Bavani G.; STOLL, Theodor; WO2014/202493; (2014); 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. 39755-95-8, name is 5-Methoxyisatin, A new synthetic method of this compound is introduced below., Formula: C9H7NO3

Description 11:5-Methoxyindolin-2-oneTo 5-methoxyisatin (0.25 g, 1.41 mmol) in ethylene glycol (1 ml) was added hydrazine hydrate (~50%, 1.5 equiv., 0.14 ml) and potassium hydroxide (1 equiv., 79 mg). The reaction mixture was heated in microwave (150C, 5 min). Tic (EtOAc : hexane, 1:1) indicated the completion of the reaction. The reaction mixture was diluted with water, acidified to pH~1 with 2M HCI and extracted into ethyl acetate. The organic layer was dried (MgS04), filtered and volatiles were removed in vacuo. The residue was purified by ISCO Combiflash (100% DCM – 5% MeOH/DCM) to give the product as an off-white solid. The results set out below indicate the final product was the title compound D1 .1H NMR (CDCI3): 8.08 (1H, br s), 6.83 (1H, s), 6.77-6.71 (2H, m), 3.75 (3H, s), 3.50 (2H, s). 13C NMR (CDCI3): 176.3, 159.5, 135.7, 126.6, 112.5, 111.8, 109.8, 55.8, 36.5.MS: (MH+41) 205.0

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; University of Greenwich; SPENCER, John; WO2012/25726; (2012); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem