Category: indolines-derivatives

Related Products of 13861-75-1, The chemical industry reduces the impact on the environment during synthesis 13861-75-1, name is Spiro[cyclopropane-1,3′-indolin]-2′-one, I believe this compound will play a more active role in future production and life.

EXAMPLE 5 N-(1-azabicyclo[2.2.2]octan-4-ylmethyl)-2′-oxo-spiro[cyclopropane-1,3′-[3’H]indole]-1′(2’H)-carboxamide, monohydrochloride STR13 To sodium hydride (92 mg, 2.31 mmol) (washed 2* with hexane) suspended in THF (1 ml) was added spiro[cyclopropane-1,3′-[3’H]indol]-2′(1’H)-one (92 mg, 0.578 mmol) and the reaction was stirred for 5 minutes. The resulting suspension was added to a solution of 20% phosgene in toluene (2.29 ml, 4.62 mmol) in THF (2 mL) and stirred for 0.5 hour. The reaction mixture was then filtered through celite and concentrated in vacuo to give a beige solid which was dissolved in THF (5 ml) and treated with a solution of 4-aminomethyl quinuclidine (81 mg, 0.578 mmol) as prepared in Example A in THF (2 ml) and stirred for 18 hours. Concentration in vacuo gave a solid which was dissolved in chloroform, washed with 1N NaOH solution, dried over K2 CO3, filtered and concentrated in vacuo to give the crude desired compound as a solid. Purification on silica gel eluding with 10% CH3 OH(NH3)/CHCl3 gave the title compound (35 mg, 19%). The free base (59 mg, 0.181 mmole) was converted to the hydrochloride salt by treatment with methanolic HCl to give the monohydrochloride (57 mg, 91%) as a solid.

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, Spiro[cyclopropane-1,3′-indolin]-2′-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; G. D. Searle & Co.; US5399562; (1995); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 20870-90-0,Some common heterocyclic compound, 20870-90-0, name is 5-Bromo-1-methyl-2-oxoindoline, molecular formula is C9H8BrNO, 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.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-1-methyl-2-oxoindoline, its application will become more common.

Reference:
Article; Basavaiah, Deevi; Lingam, Harathi; Babu, Thelagathoti Hari; Tetrahedron; vol. 74; 19; (2018); p. 2306 – 2313;,
Indoline – Wikipedia,
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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. 4702-13-0, name is N-Phthaloylglycine belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: N-Phthaloylglycine

Dissolve 2 g (9.75 mM) of N-phthaloylglycine in 20 mL of thionyl chloride, and reflux for 3 hours. At the end of that time, the thionyl chloride is evaporated under reduced pressure with the rotary evaporator. The product obtained is taken up three times in 50 mL of toluene, and subjected each time to evaporation under reduced pressure. At the end of the third evaporation, the product obtained is kept under vacuum for 30 minutes, then is taken up again in 20 mL of dry dichloroethane and stored as such until use.

The synthetic route of 4702-13-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Universite De Nantes; Universite de Bourgogne; Institut National de la Sante et de la Recherche Medicale (INSERM); Robert, Jean-Michel; Troy-Fioramonti, Stephanie; Demizieux, Laurent; DeGrace, Pascal; US2018/265498; (2018); A1;,
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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., Safety of 6-Aminoindolin-2-one

6-(Morpholin-4-yl)-2-oxindole 6-Amino-2-oxindole (2.2 g), 4.0 g 2,2′-dibromoethyl ether and 7.9 g sodium carbonate were refluxed in 20 ml ethanol overnight, concentrated and diluted with 50 ml of water. The mixture was extracted three times with 50 ml of ethyl acetate and the organic extracts combined, washed with 20 ml of brine, dried over anhydrous sodium sulfate and concentrated to dryness. The solid was chromatographed on a column of silica gel (ethyl acetate:hexane (1:1) containing 0.7percent acetic acid) to give 1.2 g (37percent yield) of the title compound as a beige solid.

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; SUGEN, Inc.; US2003/69421; (2003); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 87-48-9, 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. 87-48-9, name is 5-Bromoindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a stirred mixture of isatins 3a-c (3.4 mmol), potassium carbonate(0.94 g, 6.8 mmol) and catalytic amount of potassium iodidein dry DMF (10 mL), the appropriate alkyl halide 5a-d (3.7 mmol) or benzyl bromide 5e (0.63 g, 3.7 mmol) was added, and the mixture was heated under reflux for 3 h. Then, the reaction mixture was poured into ice-water, the obtained solid was collected, washed several times with water, and recrystallized from ethyl alcohol to afford the N-substituted isatin derivatives 6a-o [27].

The chemical industry reduces the impact on the environment during synthesis 5-Bromoindoline-2,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Article; Abo-Ashour, Mahmoud F.; Eldehna, Wagdy M.; Nocentini, Alessio; Bonardi, Alessandro; Bua, Silvia; Ibrahim, Hany S.; Elaasser, Mahmoud M.; Kry?tof, Vladimir; Jorda, Radek; Gratteri, Paola; Abou-Seri, Sahar M.; Supuran, Claudiu T.; European Journal of Medicinal Chemistry; vol. 184; (2019);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 774-47-0, name is 5,6-Difluoroindoline-2,3-dione, molecular formula is C8H3F2NO2, 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. Product Details of 774-47-0

General procedure: In a 15 mL quartz tube equipped with a magnetic stirrer bar, isatin (1 mmol), 1,3-dicarbonyl compound (1 mmol), malononitrile (1 mmol), and Na2 eosin Y (0.02 mmol) were added successively in ethyl lactate/water (3:1, 2 mL). The reaction tube was exposed to green LED (520e525 nm, 10 W) irradiation at a distance of approximately 3 mm from bottom of the tube (SI, Fig. S1) at room temperature in air with stirring for an appropriate time. The reaction progress was monitored by TLC. Upon completion, water was added to the mixture and the solid precipitate was filtered and washed with ethanol to obtain the desired pure product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 774-47-0, its application will become more common.

Reference:
Article; Chen, Meng-Nan; Di, Jia-Qi; Li, Jiao-Mian; Mo, Li-Ping; Zhang, Zhan-Hui; Tetrahedron; (2020);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 65435-04-3, A common heterocyclic compound, 65435-04-3, name is 5-(2-Chloroacetyl)indolin-2-one, molecular formula is C10H8ClNO2, 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 13 (FROM TABLE 3) 3-[4-(2-Carboxy-ethyl)-3-methyl-1H-pyrrol-2-ylmethylene]-2-oxo-2,3-dihydro-1H-indole-5-carboxylic acid 2-Oxindole (6.7 g) was added to a stirred suspension of 23 g aluminum chloride in 30 mL dichloroethane in an ice bath. Chloroacetyl chloride (11.3 g) was slowly added and hydrogen chloride gas was evolved. After ten minutes of stirring, the reaction was warmed to 40..50 C. for 1.5 hours. Thin layer chromatography (ethyl acetate, silica gel) showed no remaining starting material. The mixture was cooled to room temperature and poured into ice water. The precipitate was collected by vacuum filtration, washed with water and dried under vacuum to give 10.3 g (98%) of 5-chloroacetyl-2-oxindole as an off-white solid.

The synthetic route of 65435-04-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sugen, Inc.; US6878733; (2005); 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. 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., SDS of cas: 5332-26-3

Preparation 5Preparation of 3-({r(1 ,1-dimethylethyl)oxy1carbonyl}amino)-2- (phenylmethyl)propanoic acida) diethyl 2-[(1 ,3-dioxo-1 ,3-dihydro-2/-/-isoindol-2-yl)methyl]-2- (phenylmethyl)butanedioateTo a suspension of NaH (2.2 g, 54 mmole) in THF (200 ml.) was added diethyl 2-(phenylmethyl)butanedioate (12.5 g, 49.9 mmole). After 30 min at RT, bromomethyl phthalimide was added to the reaction mixture and the contents were stirred for 14 h at RT. The reaction was quenched with H2O (15 ml_), diluted with Et2O (300 ml.) and layers separated. The organic layer was concentrated under vacuum and the resulting residue recrystallized from EtOH (0) to give the title compound (13 g, 64%) as a white solid: LCMS (ES) m/z 410 (M+H)+.

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; SMITHKLINE BEECHAM CORPORATION; WO2008/121786; (2008); 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. 104618-31-7, name is 2-(4-Hydroxycyclohexyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Safety of 2-(4-Hydroxycyclohexyl)isoindoline-1,3-dione

Step 2 A solution of 2-(4-hydroxycyclohexyl)-1H-isoindole-1,3(2H)-dione (3.10 g, 12.6 mmol) in CH2Cl2 (25.0 mL) was added to a slurry of PCC (4.10 g, 19.0 mmol) in CH2Cl2 (15.0 mL) and stirred at room temperature for 3.5 hours. The reaction was diluted with Et2O (60.0 mL), decanted and the residue swirled with Et2O (2*40.0 mL). The combined ether layers were filtered through florisil and concentrated in vacuo to dryness, and the residue was recrystallized from ethyl acetate/hexane to give 2.01 g (65%) of 2-(4-oxocyclohexyl)-1H-isoindole-1,3(2H)-dione as colorless needles: mp 140.3-142.1 C.; 1H NMR (400 MHz, CDCl3) delta7.84, 7.74, 4.64, 2.72, 2.54, 2.09; 13C NMR (100 MHz, CDCl3) delta208.9, 168.1, 134.1, 131.9, 123.3, 48.4, 39.9, 28.6; IR (mull) 3062, 3031, 2958, 2949, 2919, 2885, 1775, 1762, 1721, 1708, 1611, 1465, 1436, 1419, 1393, 1379, 719 cm-1; HRMS (FAB) calcd for C14H14NO3: 244.0974, found 244.0976; Anal. Calcd for C-14H14NO3: C, 69.12; H, 5.39; N, 5.76. Found: C, 68.87; H, 5.47; N, 5.73.

The synthetic route of 104618-31-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Fu, Jian-Min; US2003/100596; (2003); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 341988-36-1, These common heterocyclic compound, 341988-36-1, name is Methyl indoline-6-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.

General working procedure GWP II-acylation: A solution of the acid chloride B (2 equiv.) was added at room temperature to a solution of the amino acid ester A (1 equiv.) and diisopropylethylamine (1 to 3 equiv.) in dichloromethane. The reaction mixture was stirred for 12 h at room temperature, N,N-dimethylethane-1,2-diamine (1 to 3 equiv.) was added, and stirring was carried out for 1 h at room temperature. The mixture is then washed 3.x. with a 1N HCl solution, dried over sodium sulfate and concentrated under reduced pressure. Purification by column chromatography (silica; ethyl acetate/hexane) yielded the desired product.

Statistics shows that Methyl indoline-6-carboxylate is playing an increasingly important role. we look forward to future research findings about 341988-36-1.

Reference:
Patent; Gruenenthal GmbH; US2010/234340; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem