Author: Jessica.F

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

These common heterocyclic compound, 118-29-6, name is 2-(Hydroxymethyl)isoindoline-1,3-dione, 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. Quality Control of 2-(Hydroxymethyl)isoindoline-1,3-dione

6.1 5-Phthalimidomethyl-2,3,3-trimethylindolenine To a stirred solution of 2,3,3,-trimethylindolenine (20 g, 126 mmol) in concentrated sulphuric acid (100 ml) at ambient temperature was added portionwise N-hydroxymethylphthalimide (20 g, 114 mmol). After 70 hours the reaction mixture was poured onto ice and made basic with concentrated ammonium hydroxide. The resulting precipitate was filtered and dried. The product was obtained as a yellow solid (34.84 g, 87%).

The synthetic route of 2-(Hydroxymethyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Carnegie Mellon University; US6686145; (2004); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

3891-07-4, name is 2-(2-Hydroxyethyl)isoindoline-1,3-dione, 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. Recommanded Product: 3891-07-4

Into the reaction tank, put 350 kg of toluene, stirring temperature, distillation of toluene, after the liquid in the water separator is filled, keep the reflux water for 60 minutes, and take a sample to measure the water, when the water content of the reflux liquid is ?0.2%, the reflux is changed to distillation, distilled 45kg of toluene (worked ethyl 4-chloroacetoacetate as a dilution solvent), stirring and lowering the temperature, when the temperature in the tank drops to 45 C, the reaction tank is filled with nitrogen, continue to cool down at-5 C, under stirring add 40 kg of N-(2-hydroxyethyl)-phthalimide, and the add 20 kg of sodium hydride, after the addition, cover the can lid, stirring at -5 C, into the metering tank draw 38.4 kg of ethyl 4-chloroacetoacetate, 45 kg of toluene and mix well, at -5 C condition added the drops of ethyl 4-chloroacetoacetate toluene solution, the dropping time is controlled at 4 hours, after the addition, the reaction is stirred and the temperature is slowly increased, the temperature of the reaction solution is slowly raised at 32 C within 5 hours, the reaction time is more than 12 hours, and the temperature is raised at 45 C to continue the heat preservation, until the reaction is complete, cool down, control the internal temperature of 25 C, add 61 kg of glacial acetic acid, after the addition, continue stirring to make the material in the reaction solution stir evenly, and the internal temperature is controlled at 25 C, add 180kg of water, add, continue to stir for 30 minutes, stop nitrogen filling, stop stirring, let stand, divide the water layer into the barrel and transfer the toluene layer to the washing tank, transfer the water layer into the reaction tank, into the reaction tank add 75kg of toluene, stir and let stand, the water layer is separated into barrels, and the toluene layer is transferred to a washing tank, the water layer is transferred into the reaction tank, 75 kg of toluene is added into the reaction tank, stirred, and allowed to stand, and the water layer was separated, combine the toluene layer into a water wash tank, add 100kg of 25% salt water to the washing tank, stir for 15 minutes, let stand for 30 minutes, and separate the water layer, obtained 4-[(2-phthalimido) ethyoxyl] ethyl acetoacetate toluene solution

The synthetic route of 3891-07-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Fenglin Biological Technology Co., Ltd.; Zheng Yulin; Chen Yushuang; Gao Huanhuan; Liu Lijuan; Yu Yaoying; (12 pag.)CN108358833; (2018); A;,
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. 675109-26-9, name is 6-Bromoisoindolin-1-one, A new synthetic method of this compound is introduced below., Application In Synthesis of 6-Bromoisoindolin-1-one

To a solution of 6-bromo-2,3-dihydro-isoindol-l-one (1 equiv) in dry dioxan (0.1 M) were added bis(pinacolato)diboron (1.1 equiv), potassium acetate (3.5 equiv) and dppf (0.05 equiv). The reaction mixture was degassed with nitrogen for 20 minutes. PdCl2(dppf) (0.05 equiv) was added to the reaction mixture, which was degassed for a further 5 minutes. The reaction mixture was heated to 70C for 2 hours under nitrogen then heated to 1200C for 16 hours. The reaction mixture was partitioned between EtOAc and water. The aqueous phase was further extracted with EtOAc and the combined organic phases dried (MgSO4), filtered and concentrated in vacuo. The residue was sonicated in EtOAc, the suspension was filtered onto a sintered funnel and the collected grey solid was dried and used without further purification. 6-(4,4,5,5-Tetramethyl-[l,3,2]dioxaborolan-2-yl)-2,3-dihydro-isoindol-l-one: (82 % yield, 29 % purity, main impurity being the boronic acid 43 %) m/z (LC-MS, ESP): 519.5 [2M+H]+ R/T = 3.38 min

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; KUDOS PHARMACEUTICALS LIMITED; WO2008/23161; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem