Category: indolines-derivatives

Adding a certain compound to certain chemical reactions, such as: 480-91-1, name is Isoindolin-1-one, 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 480-91-1, Quality Control of Isoindolin-1-one

Intermediate 6-1Preparation of 2-(3-fluoro-4-iodopyridin-2-yl)isoindolin-1-one A mixture of 3-fluoro-2,4-diiodopyridine (300 mg, 0.860 mmol), isoindolin-1-one (114 mg, 0.860 mmol), copper (I) iodide (8.19 mg, 0.043 mmol), potassium carbonate (238 mg, 1.720 mmol) and N1,N2-dimethylethane-1,2-diamine (7.58 mg, 0.086 mmol) in 1,4-dioxane (5 mL) was heated at 110 C. in a sealed tube for 15 h. The mixture was cooled to rt, filtered through Celite and washed with DCM. The filtrate was concentrated and the residue was purified by column chromatography (eluting with a gradient from 80:20 hexane-EtOAc to EtOAc) to give 2-(3-fluoro-4-iodopyridin-2-yl)isoindolin-1-one (125 mg, 41%). 1H NMR (400 MHz, chloroform-d) delta 7.86-8.06 (2H, m), 7.41-7.71 (4H, m), 5.04 (2H, s). Mass spectrum m/z 354.9 (M+H)+.

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, Isoindolin-1-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bristol-Myers Squibb Company; US2010/160303; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 181140-34-1, 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. 181140-34-1, name is (R)-(-)-N-(2,3-Epoxypropyl)phthalimide belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Compounds 3-7 have been synthesized using a procedure originallyreported by Roehrig et al.16 Chiral amine or amino alcohol(0.6 mmol, 1.2 equiv) in 10 mL isopropanol was added to the solutionof (R)-N-(2,3-epoxypropyl)phthalimide (102 mg, 0.50 mmol)in 10 mL of isopropanol at in an ice bath and stirred for 1 h. thenrefluxed for 12 h. The reaction monitored by TLC. Solvent was removed by rotary evaporator under reduced pressure after completionof the reaction.

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, (R)-(-)-N-(2,3-Epoxypropyl)phthalimide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Karakaplan, Mehmet; Jameel, Basam; Tetrahedron Asymmetry; vol. 27; 14-15; (2016); p. 597 – 602;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 61-70-1, These common heterocyclic compound, 61-70-1, name is 1-Methylindolin-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.

Stage A: 1-Methyl-2-Indolinethione 148 g (1.76 mol) of sodium bicarbonate are added in 20-gram portions with brisk stirring and at room temperature to a suspension of 130 g (0.8 mol) of 1-methyl-2-indolinone, prepared according to R. A. ABRAMOVITCH and D. H. HEY (J. Chem. Soc., 1954, 1699) and 133 g (0.3 mol) of phosphorus pentasulfide in 1.30 1 of anhydrous tetrahydrofuran. After 10 hours’ stirring at room temperature, the mixture is filtered and the filtrate is concentrated on a water bath under vacuum. The residue is taken up with a water/ice mixture and the resulting mixture is extracted three times with chloroform. The organic phase is washed with water and then with saturated aqueous sodium chloride solution, dried and evaporated to dryness. The residue is recrystallized in methanol. Yield: 93%. Melting point: 177-118 C. Analysis: Calculated: C: 66.22, N: 8.58, S: 19.64. Found: C: 66.62, N: 8.63, S: 19.76.

The synthetic route of 61-70-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Adir et Compagnie; US5030646; (1991); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 1168150-46-6, 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. 1168150-46-6, name is (E)-Methyl 3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

N-methyl-2-(4-methylpiperazin-1-yl)-N-(5-aminopyridin-2-yl)acetamide (205mg, 0.78mmol) and methyl (E)-3-(methoxy(phenyl)methylene)-2-oxoindole-6-carboxylate (200mg, 0.65mmol) placed in 15mL of methanol was heated to 70 C, 13h of holding, and then cooled to room temperature, concentrate.The residue was purified by silica gel column (ethyl acetate / petroleum ether = 1/5 to 4/1) to give a yellow oil was isolated, after recrystallization (ethyl acetate / petroleum ether = 1/8) to give a bright yellow solid, methyl (Z)-(((6-(N-methyl-2-(4-methylpiperazin-1-yl)acetamido)pyridin-3-yl)amino(phenyl)methylene))-2-oxoindole-6-carboxylate (120mg, 34%).

The synthetic route of (E)-Methyl 3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shandong Hengli medical science and Technology Co Ltd; Luo, haoxian; Wang, aichen; (42 pag.)CN103848814; (2016); B;,
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. 39755-95-8, name is 5-Methoxyisatin, This compound has unique chemical properties. The synthetic route is as follows., Formula: C9H7NO3

A stirred solution of 5-methoxyisatin (0.1 mol) in hydrazine hydrate (60 ml) was heated to 140C for 4 h. The reaction mixture was cooled to room temperature, poured into 300 ml of ice water, and acidified to pH 2 with 10% hydrochloric acid. After standing at room temperature for one night the precipitate was collected by vacuum filtration, washed with water, and dried under vacuum (35% yield).

According to the analysis of related databases, 39755-95-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wang, Lihong; Li, Zhanshan; Lu, Lianhong; Zhang, Wei; Tetrahedron; vol. 68; 5; (2012); p. 1483 – 1491;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 1201923-48-9, 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. 1201923-48-9, name is (S)-tert-Butyl (1-(1,3-dioxoisoindolin-2-yl)-3-(3-fluorophenyl)propan-2-yl)carbamate belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A mixture [(S)-1-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-2-(3-fluoro-phenyl)-ethyl]carbamic acid tert-butyl ester (1.203 g, 3 mmol) and trifluoroacetic acid-dichloromethane (15 mL, 2:1) was stirred at room temperature for 1 hour and then concentrated under reduced pressure to give crude 2-[(S)-2-amino-3-(3-fluoro-phenyl)-propyl]-isoindole-1,3-dione trifluoroacetic acid salt. (Yield 1.516, 123%).

The synthetic route of (S)-tert-Butyl (1-(1,3-dioxoisoindolin-2-yl)-3-(3-fluorophenyl)propan-2-yl)carbamate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Anderson, Kevin; Chen, Yi; Chen, Zhi; Luk, Kin-Chun; Rossman, Pamela Loreen; Sun, Hongmao; Wovkulich, Peter Michael; US2012/184542; (2012); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 193354-13-1,Some common heterocyclic compound, 193354-13-1, name is 5-Iodoindolin-2-one, molecular formula is C8H6INO, 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.

3-[5-(5-Iodo-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-2,4-dimethyl-1H-pyrrol-3-yl]-propionic acid 3-(2-Carboxyethyl)-2,4-dimethyl-5-formylpyrrole (97.5 mg), 130 mg 5-iodo-2-oxindole, and 75 muL piperidine in 3 mL of ethanol were heated at 95 C. for 5 hours. The reaction mixture was cooled and concentrated. The residue was suspended in 6 N aqueous hydrochloric acid. The precipitate was filtered, washed with water to pH 6 and dried in a vacuum oven overnight to give 155 mg (71%) of the title compound as an orange solid. 1H-NMR (360 MHz, DMSO-d6): delta 13.41 (s, br, 1H, NH-1′), 12.03 (s, br, 1H, COOH), 10.79 (s, br, 1H, NH-1), 8.12 (d, J=1.70 Hz, 1H, H-4), 7.65 (s, 1H, H-vinyl), 7.36 (dd, J=1.70, 7.93 Hz, 1H, H-6), 6.79 (d, J=7.93 Hz, 1H, H-7), 2.64 (t, J=7.76 Hz, 2H, CH2CH2COOH), 2.34 (t, J=7.76 Hz, 2H, CH2CH2COOH), 2.29 (s, 3H, CH3), 2.27 (s, 3H, CH3); MS m/z (relative intensity, %) 437 ([M+1]+, 100).

The synthetic route of 193354-13-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sugen, Inc.; US6395734; (2002); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 959235-95-1, name is 6-(Trifluoromethoxy)indoline, 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. Safety of 6-(Trifluoromethoxy)indoline

HATU (2.10 g, 5.52 mmol) was added to a mixture of 6-(trifluoromethoxy)indoline [CAS 953906-76-8] (747 mg, 3.68 mmol), 2-((3-(2-(terf-butoxy)ethoxy)-5-methoxy- phenyl)amino)-2-(4-chlorophenyl)acetic acid 3c (1 .5 g, 3.68 mmol) and diisopropylethylamine (1 .82 mL, 1 1 .03 mmol) in DMF (30 mL). The resulting mixture was stirred at room temperature for 12 h. The mixture was diluted with water and extracted with EtOAc. The organic layer was separated, dried over MgSO4, filtered and the solvent was evaporated under reduced pressure. Purification was carried out by flash chromatography on silica gel (15-40 muiotatauiota, 40 g, heptane/EtOAc 85/15). The pure fractions were combined and evaporated to dryness to give 2-((3-(2-(fe/t-butoxy)ethoxy)-5-methoxyphenyl)amino)-2-(4-chloro- phenyl)-1 -(6-(trifluoromethoxy)indolin-1 -yl)ethanone 3d (1 .33 g).

The synthetic route of 6-(Trifluoromethoxy)indoline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICALS, INC.; KATHOLIEKE UNIVERSITEIT LEUVEN; BARDIOT, Dorothee Alice Marie-Eve; BONFANTI, Jean-Francois; KESTELEYN, Bart Rudolf Romanie; MARCHAND, Arnaud Didier M; RABOISSON, Pierre Jean-Marie Bernard; (76 pag.)WO2017/167953; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

41910-64-9, name is 4-Chloroindoline, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Quality Control of 4-Chloroindoline

A mixture of 4-chloroindoline (2.88 g) and D-glucose (3.38 g) in ethyl alcohol (150 ml)-H2O (10 ml) was refluxed under argon atmosphere overnight. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (chloroform:methanol=100:0-88:12) to give 4-chloro-1-(beta-D-glucopyranosyl)indoline (3.35 g) as a colorless foam. APCI-Mass m/Z 316/318 (M+H). 1H-NMR (DMSO-d6) delta 2.87-3.02 (m, 2H), 3.07-3.12 (m, 1H), 3.20-3.32 (m, 2H), 3.38-3.47 (m, 2H), 3.51-3.60 (m, 2H), 3.68-3.73 (m, 1H), 4.34-4.37 (m, 1H), 4.63 (d, J=8.3-Hz, 1H), 4.93 (d, J=5.1 Hz, 1H), 5.03 (d, J=4.0 Hz, 1H), 5.06 (d, J=4.5 Hz, 1H), 6.53 (d, J=8.0 Hz, 1H), 6.60 (d, J=8.0 Hz, 1H), 6.99 (t, J=7.9 Hz, 1H).

The synthetic route of 41910-64-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tanabe Seiyaku Co., Ltd.; US2008/27122; (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. 88150-75-8, name is Ethyl 4-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)-3-oxobutanoate, A new synthetic method of this compound is introduced below., SDS of cas: 88150-75-8

Example 8a synthetic process of amlodipine besylate,The difference from Embodiment 1 is thatStep three is: in the reaction tank,Into a toluene solution of 4-[(2-phthalimido)ethoxy]acetic acid ethyl acetate,Distilled under reduced pressure at 70 C,Fill the water separator and continue to reflux under reduced pressure.Until the water content in the reflux liquid is ?0.2%, the temperature is lowered to 35 C, 27 kg of 2-chlorobenzaldehyde is added, and the internal temperature is maintained at 35 C.Add 1.5 kg of hexahydropyridine and stir for 30 minutes.Under the condition of 65 C, -0.09 Mpa, the water was refluxed under reduced pressure for 12 hours or more, the temperature was lowered to 35 C, and 120 kg of water was added.Stir,Let stand for 30 minutes,Layered, the lower aqueous layer is recovered, and the upper layer is a toluene solution of 2-(2-chloroindol)-4-[(2-phthalimido)ethoxy]acetic acid ethyl acetate; The yield of amlodipine was 91.2%, and the purity was 99.5%.

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; Shanghai Fenglin Biological Technology Co., Ltd.; Zheng Yulin; Chen Yushuang; Liu Lijuan; Gao Huanhuan; Yu Yaoying; (13 pag.)CN108456160; (2018); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem