Month: August 2021

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;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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,
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 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;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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,
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. 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;,
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. 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;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 102359-00-2, 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. 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of 4 (1.77 g, 10 mmol) in 120 mL ofdichloromethane and 10 mL of DMF was added 4-methylmorpholine or DIEA (10 mL), TBTU (4.81 g, 15mmol) and aniline derivatives (11 mmol). The mixture wasstirred under room temperature for 18 h and washed in turnwith 5% sodium carbonate solution, 5% citric acid solutionand saturated sodium chloride solution. After dried byanhydrous sodium sulfate, the organic layer was evaporatedto dryness. The residue was purified with flash chromatography(CH2Cl2:CH3OH, 50:1) to afford intermediates 5a-5l, which were used in the next step in short time. To asolution of compounds 5a-5l (1.0 mmol) in 10 mL methanolwas added piperidine (30 muL) and 1H-pyrrole-2-carbaldehyde/furan-2-carbaldehyde (1.0 mmol). The mixturewas stirred at 60 C for 5 h and cooled to room temperature.After kept in fridge overnight, the target compounds 6a-6land 7a-7l were obtained in high yields.

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

Reference:
Article; Ai, Juntao; Lv, Meng; Li, Xiaohui; Chen, Zhuo; Hu, Gaoyun; Li, Qianbin; Medicinal Chemistry Research; vol. 27; 1; (2018); p. 161 – 170;,
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. 3485-84-5, name is N-Vinylphthalimide, A new synthetic method of this compound is introduced below., Recommanded Product: 3485-84-5

N-Vinyl phthalimide (0.100 g, 0.577 mol) was treated with 4N HCl/dioxane (0.433 mL, 1.73 mmol) at 25 C. After 3 h the reaction mixture was concentrated under reduced pressure to provide an off white solid (112 g, 93% yield). 1H NMR (400 MHz, CDC13) delta 7.95-7.89 (m, 2H), 7.83-7.77 (m, 2H), 6.32 (q, J=6.8 Hz, 1H), 2.19 (d, J=6.8 Hz, 2H), LC tr=3.05 minutes (C-18 column, 5 to 95% acetonitrile/water over 6 minutes at 1.7 mL/min with detection 254 nm, at 23 C).

The synthetic route of 3485-84-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SARMONT LLC; MARTINEZ, Eduardo J.; TALLEY, John J.; JEROME, Kevin D.; BOEHM, Terri L.; WO2015/108835; (2015); A1;,
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, Quality Control of 5-Nitroindoline

Example XIV; tert-butyl 5-nitro-2.3-dihvdro-indole-1 -carboxylate; 5 g 5-nitro-2,3-dihydro-1 H-indole are dissolved in 70 ml acetonithle. 7.3 g di- tert-butyl-dicarbonate and 900 mg 4-dimethylaminopyridine are added thereto. After stirring for 24 hours at ambient temperature the mixture is divided between 1 N HCI and ethyl acetate. The aqueous phase is extracted with ethyl acetate and the combined organic phases are washed with saturated sodium hydrogen carbonate solution and saturated sodium chloride solution.After drying with magnesium sulphate the solvents are eliminated in vacuo.The residue is extracted from diisopropylether/petroleum ether.Yield: 6.6 g (82 % of theory) Mass spectrum (ESI+): m/z = 265 [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, 5-Nitroindoline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WO2008/113760; (2008); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem