Category: indolines-derivatives

Related Products 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.

General procedure: All reactions were conducted in 10 mL glass vials fitted with crimpcap septum caps. The reaction vial, equipped with a magnetic stir bar,was charged under an N2 atmosphere with 1-methylindolin-2-one (4)(73.6 mg, 0.5 mmol), Pd2(dba)3 (10 mg, 0.011 mmol, 2.5 mol%), i-Pr-BI-DIME (7) (0.022 mmol, 5 mol%), LiHMDS (1 M in toluene, 0.55 mL,0.55 mmol) and the aryl halide (1.1 equiv), then sealed with a crimpcap septum. THF (0.5 mL) and toluene (0.5 mL) were added via syringe and the reaction was heated to 70 C for 4-24 h. The reaction mixture was cooled to room temperature then filtered through a Celite pad with EtOAc (5 mL) as eluent. The filtered solution waswashed with H2O (3 mL), dried over MgSO4 and then concentrated under reduced pressure. The crude residue was purified using a 12 g silica column (30% EtOAc/hexanes) to afford the corresponding oxindole product.

Statistics shows that 1-Methylindolin-2-one is playing an increasingly important role. we look forward to future research findings about 61-70-1.

Reference:
Article; Mangunuru, Hari P. R.; Malapit, Christian A.; Haddad, Nizar; Reeves, Jonathan T.; Qu, Bo; Rodriguez, Sonia; Lee, Heewon; Yee, Nathan K.; Song, Jinhua J.; Busacca, Carl A.; Senanayake, Chris H.; Synthesis; vol. 50; 22; (2018); p. 4435 – 4443;,
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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. 446292-07-5, name is (R)-2-(2-Hydroxy-3-((4-(3-oxomorpholino)phenyl)amino)propyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 446292-07-5

Example – 6: Preparation of 2-5(S)-{2-Oxo-3-[4-(3-oxo-morpholin-4-yl) phenyl]- oxazolidin-5-ylmethyl}-isoindoIe-l,3-dione (III)60 gms of 2-{2-Hydroxy-3-[4-(3-oxo-mo holin-4-yl)phenylamino]-propyl}-isoindole- 1 ,3-dione and 180 ml of methylene chloride were charged into a clean and dry 4 neck R.B. flask. 29 gms of carbonyl diimidazole was added at about 30C and the resultant reaction mixture was stirred at about 30C for about 20 hours. After completion of the reaction, the reaction mixture was washed with water and the solvent was distilled completely to give 55gms of the title compound.

The synthetic route of 446292-07-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SYMED LABS LIMITED; MOHAN RAO, dodda; KRISHNA REDDY, pingili; ANNA REDDY, ambati; VENKAT REDDY, buthukuri; WO2012/32533; (2012); A2;,
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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. 71294-07-0, name is 5,6-Difluoroindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 71294-07-0

5,6-difluoro-2,3-dihydro-1H-indole Under an argon atmosphere 0.30 g (1.8 mmol) 5,6-difluoro-1,3-dihydro-indol-2-one were dissolved in 10 mL THF and 3.0 mL of a 1 M borane in THF solution were added dropwise. Then the reaction mixture was heated for 2 h to 70 C. and then cooled. After the addition of 3 mL MeOH a further 5 mL of a 4N aqueous hydrochloric acid solution were added and the mixture was refluxed for 1 h. The organic phase was evaporated down, the aqueous phase was washed with DCM and then made alkaline with a 4N aqueous sodium hydroxide solution and extracted several times with EtOAc. The combined organic phases were dried on sodium sulphate, filtered and evaporated down. Yield: 160 mg (47% of theory) ESI-MS: m/z=156 (M+H)+

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 71294-07-0.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/195954; (2011); A1;,
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Adding a certain compound to certain chemical reactions, such as: 446292-08-6, name is (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione, 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 446292-08-6, category: indolines-derivatives

5L three neck flask was added to the raw material A (100.0g, 240mmol) and toluene 700ml (7ml / g), being stirred suspension was heated to 80-85 , and then at 75-80 deg.] C, the 145ml (2.4mol ) ethanolamine was added to the suspension, and the mixture was stirred at 80-85 2 hours, and during this time the solid gradually dissolved.After completion of the reaction, the separation layer alkanolamines, alkanolamine layer was washed with toluene twice, each time 100ml, toluene layers were combined and concentrated to give an oily object.Recrystallization from methanol was added powdery crystals, 30 dried under reduced pressure for 10 hours to obtain a solid of about 66.99g, i.e. intermediate B.Yield was about 95.87%, Ms as 291.30, HPLC 99.92%.Intermediate B HPLC chromatogram see figure 7.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione, and friends who are interested can also refer to it.

Reference:
Patent; Shenzhen Yu Han Pharmaceutical Co., Ltd.; Yuan, Huixing; Li, Guotao; Liu, Hui; Ma, Yaping; Yuan, Jiancheng; (11 pag.)CN105777732; (2016); A;,
Indoline – Wikipedia,
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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 2058-72-2 as follows. Quality Control of 5-Bromo-1-methylindoline-2,3-dione

General procedure: To a solution of isatin derivative 1a-r (1 mmol) in anhydrous toluene (1 mL, 1.0 M), MgSO4 (3 mmol) and NH3 solution 2M in methanol (2 mmol) were added. The reaction was stirred 8 hours at room temperature and then the mercapto-derivative 2a-c was added (1.1 mmol). The resulting mixture was stirred for further 30 minutes at the same temperature. The reaction was diluted with CH2Cl2 (5 mL) and then the solvent was removed under reduced pressure. The crude was purified by flash chromatography (FC)

According to the analysis of related databases, 2058-72-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Rainoldi, Giulia; Begnini, Fabio; Silvani, Alessandra; Lesma, Giordano; Synlett; vol. 27; 20; (2016); p. 2831 – 2835;,
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These common heterocyclic compound, 20870-78-4, name is 5-Bromoindolin-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. Recommanded Product: 5-Bromoindolin-2-one

5-Bromo-1 ,3-dihydro-indol-2-one (Aldrich, 1.06 g, 5 mmol) was coupled with bis(pinacolato)diboron (Aldrich, 1.52 g, 6 mmol) catalyzed by PdCI2(dppf)2-CH2CI2 (Aldrich, 82 mg, 0.1 mmol) using KOAc (Aldrich, 0.98 g, 10 mmol) as base in dioxane (anhydrous, Aldrich, 50 ml_) at 8O0C for 10h. After being cooled down to ambient temperature, the mixture was diluted with EtOAc (50 ml_) and washed with brine (2 x 10 ml_). The organic solution was then concentrated under vacuum. The title compound was purified by chromatography (SiO2, hexane : EtOAc, 70:30, Rf. 0.5) as a solid (0.96 g, yield, 74%). 1H NMR (300 MHz, CDCI 3) delta 1.24 (s, 3 H), 1.28 EPO (s, 3 H), 1.34 (s, 6 H), 3.69 (s, 2 H), 6.86 (d, J=7.8 Hz, 1 H), 7.57 – 7.78 (m, 2 H) ppm. MS (DCI/NH3): 260 (M+H)+.

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

Reference:
Patent; ABBOTT LABORATORIES; WO2006/65233; (2006); A1;,
Indoline – Wikipedia,
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Reference of 496-12-8, A common heterocyclic compound, 496-12-8, name is Isoindoline, molecular formula is C8H9N, 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.

Pyridine (6.56 mL, 81.1 mmol) and N,N-dimethyl-4-aminopyridine (248 mg, 2.03 mmol) were added to a solution of 2,3-dihydro-1H-isoindole (8.08 g, 40.6 mmol) in chloroform (120 mL) at room temperature. The mixture was cooled to 0 C, and trifluoroacetic anhydride (6.77 mL, 48.7 mmol) was added dropwise to the mixture. After the addition, the reaction mixture was warmed to room temperature and stirred for 4 h. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with ethyl acetate. The mixture was then washed with 1 mol/L hydrochloric acid, saturated aqueous NaHCO3, and brine. The organic layer was dried over anhydrous MgSO4 and then concentrated under reduced pressure. The resulting residue was purified using a silica gel column eluted with 10% ethyl acetate/n-hexane to afford 8 (8.66 g, 99%) as a light brown powder: 1H NMR (300 MHz, CDCl3) delta 4.93 (s, 2H), 5.04 (s, 2H), 7.22-7.43 (m, 4H); MS (ESI/APCI Dual): m/z 216 [M+H]+.

The synthetic route of 496-12-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Busujima, Tsuyoshi; Tanaka, Hiroaki; Shirasaki, Yoshihisa; Munetomo, Eiji; Saito, Masako; Kitano, Kiyokazu; Minagawa, Toshiya; Yoshida, Koji; Osaki, Naoto; Sato, Nagaaki; Bioorganic and Medicinal Chemistry; vol. 23; 17; (2015); p. 5922 – 5931;,
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Electric Literature of 101207-45-8, 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. 101207-45-8, name is 2-(4-Methylbenzyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 2-(4-methylbenzyl)isoindoline-l,3-dione (1 g, 3.8 mmol) and hydrazine hydrate (752 mg, 15 mmol, 730 pL) in MeOH (10 mL) was stirred at 20C for 3 hours. The mixture was concentrated in vacuo. The residue was purified by silica gel chromatography (0928) (dichloromethane:methanol (with 5% ammonia in water) = 0:1 to 5:1) to give p-tolylmethanamine (160 mg).

The chemical industry reduces the impact on the environment during synthesis 2-(4-Methylbenzyl)isoindoline-1,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Patent; H. LUNDBECK A/S; KEHLER, Jan; JUHL, Karsten; MARIGO, Mauro; VITAL, Paulo, Jorge, Vieira; JESSING, Mikkel; LANGGARD, Morten; RASMUSSEN, Lars, Kyhn; CLEMENTSON, Carl, Martin, Sebastian; (275 pag.)WO2019/115566; (2019); A1;,
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Reference of 552330-86-6, 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. 552330-86-6, name is 5-Bromoisoindolin-1-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Step C: (Z)-5-Bromoisoindolin-1-one O-benzyl oxime: 5-Bromoisoindolin-1-one (3.00 g, 14.1 mmol) was suspended in 100 mL chloroform at 0 C. Triethyloxonium tetrafluoroborate (4.03 g, 21.2 mmol) was added in a single portion to the mixture and the suspension was stirred from 0 C. to ambient temperature over the 48 hours. The reaction was concentrated and the residue dissolved in 150 mL ethanol and cooled to 0 C. O-benyzyl hydroxylamine HCl (4.52 g, 28.3 mmol) and sodium carbonate (4.50 g, 42.4 mmol) were added, and the reaction was stirred from 0 C. to ambient temperature for 18 hours, then concentrated, diluted with ethyl acetate, washed with 10% citric acid, dried over sodium sulfate, filtered and concentrated to a solid. The solid was purified by silica gel chromatography with 100% dichloromethane (1.69 g, 37%).

The synthetic route of 5-Bromoisoindolin-1-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Miknis, Greg; Lyssikatos, Joseph P.; Laird, Ellen; Tarlton, Eugene; Buckmelter, Alexandre J.; Ren, Li; Rast, Bryson; Schlacter, Stephen T.; Wenglowsky, Steven Mark; US2007/49603; (2007); A1;,
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Electric Literature of 3335-98-6, 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. 3335-98-6, name is 1-Phenyloxindole belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

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.

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

Reference:
Article; Basavaiah, Deevi; Lingam, Harathi; Babu, Thelagathoti Hari; Tetrahedron; vol. 74; 19; (2018); p. 2306 – 2313;,
Indoline – Wikipedia,
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