Category: indolines-derivatives

Adding a certain compound to certain chemical reactions, such as: 19155-24-9, name is 3,3-Dimethylindolin-2-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 19155-24-9, Recommanded Product: 3,3-Dimethylindolin-2-one

To a suspension of dimethyl oxidole (68 g of 74 percent strength crude, 280 mmol) in DMF (51 g, 700 mmol.) and toluene (200 rriL), a toluene solution of (Me3Si)2NLi (840 ml_, 1 M, 840 mmol) was added dropwise while keeping the mixture below 100C to give a dark solution. A solution of epoxy alcohol (76 g of 85percent strength, 350 mmol) and Ti(OiPr)4 (103 g, 360 mmol) in toluene (400 ml_) was added to the above dark solution at below 100C. The reaction mixture was stirred for 20 hours at 200C before cooling to 00C. A solution of HCI (660 g, 37percent in water) in water (750 g) was added at below 200C to give a bi-phasic mixture. The two layers were separated. The organic layer was washed with NaOH (400 ml_, 0.7 N in water, 280 mmol), and brine (230 g). The organic layer was filtered through a silica gel (150 g) plug. The silica gel plug was rinsed with. EtOAc (1100 ml_). The filtrate was concentrated in vacuo at 50°C to a volume of 240 ml_. This concentrate was diluted with CH3CN (300 ml_) to give 1-[(1S,2S)-1-(3,5-difluorophenyl)-2,3-dihydroxypropyl]- 7-fluoro-3,3-dimethyl-1 ,3-dihydro-2H-indol-2-one as a CH3CN solution, 431 g of a 20.8percent strength solution, yield: 88percent.

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, 3,3-Dimethylindolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; WYETH; WO2008/24492; (2008); A2;,
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These common heterocyclic compound, 1029691-06-2, name is 2-(3-Oxocyclopentyl)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. COA of Formula: C13H11NO3

Mix (±)-2-(3-oxo-cyclopentyl)-isoindole- 1 ,3-di- one (12.7 g, 55.3 mmol) and 4-cyanophenylhydrazine-HC1 (8.53 g, 50.3 mmol) in HOAc (200 mE) and 4N HC1 dioxane (50 mE). Using mechanical stirring, heat the reaction to 90 C. for 18 h, then add additional 4N HC1 dioxane (20 mE). Heat the reaction to 100 C. for 18 h. Dilute the reaction mixture with water (600 mE) and collect a black solid by vacuum filtration. Sonicate the solid with MeOH (200 mE), then collect and dry in a vacuum oven to give 10.94 g (66%) of a gray-brown solid. MS (mlz): 328 (M+H), 326 (M-H)

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

Reference:
Patent; Eli Lilly and Company; Benson, Charles Thomas; (29 pag.)US2017/172992; (2017); A1;,
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Related Products of 100510-65-4, 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. 100510-65-4, name is 6-Amino-3,3-dimethylindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

a) 25 g. (0.142 mol) 6-Amino-1,3-dihydro-3,3-dimethyl-(2H)-indolin-2-one in 250 ml. 2N hydrochloric acid were mixed, while cooling with ice, within the course of 15 minutes with a solution of 10.3 g. (0.15 mol) sodium nitrite in 20 ml. water and, after the addition, stirred for 15 minutes. After mixing with 2.13 g. (0.036 mol) urea, the clear solution, after stirring for a further 10 minutes, was added dropwise to a solution, warmed to 50 C., of 24.4 g. (0.5 mol) sodium cyanide, 15.2 g. (0.17 mol) cuprous cyanide and 22.6 g. (0.21 mol) sodium carbonate in 820 ml. water and heated for 5 minutes to 90 C. After cooling, the precipitate was filtered off with suction, washed with water and, after drying, recrystallized from ethanol. There were obtained 15 g. (57% of theory) 2,3-dihydro-3,3-dimethyl-2-oxo-(1H)-indole-6-carbonitrile in the form of colourless crystals; m.p. 243-246 C.

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, 6-Amino-3,3-dimethylindolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Boehringer Mannheim GmbH; US5019587; (1991); A;,
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Application of 20780-72-7, These common heterocyclic compound, 20780-72-7, name is 4-Bromoisatin, 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.

Take 4-bromo indolone 1.0g (4.4mmol) into a 25mL round bottom flask,4 mL of N, N-dimethylformamide was added,Stirring to make it fully dissolved, and then adding 1.83 g (13.2 mmol) of anhydrous potassium carbonate,Further, 1.0 g (6.6 mmol) of methyl iodide was added.The reaction at room temperature for 8h, TLC detection of raw materials disappeared, adding 30mL of water,Then, the mixture was extracted with ethyl acetate (100 mL × 3), the combined organic phases were dried over anhydrous sodium sulfate,The solvent was decanted and the residue purified by petroleum ether: ethyl acetate = 10: 1200-300 mesh silica gel column.There was obtained 0.90 g of 1-methyl-4-bromoindodione in 85percent yield.

Statistics shows that 4-Bromoisatin is playing an increasingly important role. we look forward to future research findings about 20780-72-7.

Reference:
Patent; Tianjin Kunjian Bio-pharmaceutical Co., Ltd.; Yu Peng; Han Kailin; Mao Huihua; Qiu Dongxu; (12 pag.)CN104402794; (2017); B;,
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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. 446292-08-6, name is (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Recommanded Product: 446292-08-6

2-({(5S) -2-oxo-3-[4- (3-oxo-4-morpholinyl) phenyl] -1,3-oxazolidin-5- yl} methyl)-1,3(2H) -dione (Formula 5) were added 75 ml of ethanol and 8.1 ml of a methylamine solution (concentration in water 40%) was added.The reaction mixture was then diluted with 60In Heating, Stir at this temperature for 2 hours.Confirm that the reaction is completed, and while maintaining the temperature, dilute the solution with 50 ml of ethanol and 3.04 ml of phosphoric acid, and slowly add the solution to the reaction solution. After confirming that the crystallization of the product was initiated and cooling to 20 C, the precipitated reaction product was filtered under suction. The resulting solid was dispersed in 110 ml of methanol, refluxed for 30 minutes and stirred, and then cooled to room temperature. The resulting crystals were filtered,And dried at 50 DEG C for 4 hours to obtain 11.1 g of morpholine diphosphate (Formula 2). (Yield: 96.0%)

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; IL DONG PHARMACEUTICAL CO., LTD.; LEE, Ki Yong; KWON, Jae Wook; SEO, Myeong Won; KANG, Jae Hoon; (15 pag.)KR2017/98031; (2017); A;,
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These common heterocyclic compound, 18711-13-2, name is 4,7-Dichloroindoline-2,3-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. category: indolines-derivatives

4,7-Dichloroisotin (30.05 g, 139.1 mmol, 1.0 equiv, Alfa Aesar lot 10173559) and MeOH (450 mL, 15 vol) were charged to a 2-L, three-neck, round-bottom flask equipped with nitrogen line, overhead mechanical stirrer, and a temperature probe. Diethylamine (3.25 g, 0.32 equiv, Sigma- Aldrich lot SHBD5313V) was added over 3 min (the slurry becomes dark red). A very slight increase in temperature (from 17.5 C to 18.8 C) was observed. 1- [4-(Dimethylamino)phenyl]ethanone 2 (44.3 g, 1.95 equiv, ArkPharm lot 0000197- 130717000) was then added via a plastic funnel and the funnel was rinsed with MeOH (75 mL, 2.5 vol). A decrease in the reaction temperature to 15.1 C was observed. Upon stirring for a few minutes, a dark red solution with a few undissolved particles was obtained. The solution was stirred at ambient temperature and periodically sampled for in-process control (IPC) by HPLC. After 23 h of reaction, additional diethylamine was added via syringe (1.42 g, 0.14 equiv) and the stirring continued at ambient temperature. After 40.5 h, a light slurry formed. Solid 2 was added in portions (54.1 g, 2.38 equiv, ArkPharm lot 0000197- 130717000 and 3.2 g, 0.14 equiv, TCI lot GK01-BRAH) for a total of 4.47 equiv of acetophenone 2. After 88 h of reaction, IPC by HPLC showed less than 1% AUC of isatin 1 present in the reaction mixture. A heavy precipitate had formed. After 4.5 days, the reaction mixture was concentrated under reduced pressure (water bath <40 C), then under high vacuum to afford approximately 84 g of a solid mixture, lot BIO-W-22-11. The solid was dissolved in a mixture of dichloromethane (385 mL) and MeOH (140 mL) and adsorbed over 100 g of silica gel. The solvent was removed under reduced pressure and the dry product/silica mixture was loaded onto a column containing silica gel (1 kg, pre-packed with heptanes) for a flash chromatographic purification. Elution was started with 10% ethyl acetate in heptanes and a gradient up to 100% ethyl acetate was applied, and then switched to 10% methanol in ethyl acetate. Fractions of 500 mL and up to 2 L were collected. The product containing fractions, where product had started to precipitate, were combined and concentrated down to approximately 1 L. The resulting precipitate was filtered out, reslurried in EtOAc/MeOH (75:25 ratio, 200 mL), filtered, and washed with MeOH to afford a first crop of compound. The first filtrate was concentrated to a low volume, added MeOH to precipitate a second crop of compound. Filtrates from isolation of both crops were combined, concentrated to a low volume, taken up in 25 mL of MeOH, and the resulting solid was filtered to afford a third crop of compound. All three crops were dried under high vacuum at ambient temperature for a day and at 40 C for four days. The total combined weight was 40.03 g, corresponding to 76% yield of compound (uncorrected by purity or solvent content). Solid is off-white (with a very pale yellow to peach shade. The synthetic route of 4,7-Dichloroindoline-2,3-dione has been constantly updated, and we look forward to future research findings. Reference:
Patent; TOKALAS, INC.; VERNIER, Jean-michael; (82 pag.)WO2016/57698; (2016); A1;,
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Application of 2058-72-2, These common heterocyclic compound, 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-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.

A mixture of 2- (1-benzyl-2-oxoindol-3-yl) acetic acid67.4 mg (0.24 mmol),5-Bromo-1-methyl isatin 47.7mg (0.2mmol),N, N’-2- (7-benzo benzotriazole) -N, N, N ‘, N’-tetramethyluronium hexafluorophosphate (106.4 mg, 0.28 mmol)Triethylamine 50.6 mg (0.5 mmol)And 2 mL of tetrahydrofuran were placed in a 25 mL two-necked flask,Reaction at 0 C for 6 h,The reaction solution was concentrated,Eluting with a mixed solvent of petroleum ether: ethyl acetate ratio of 3: 1 as elution column,Collecting the eluted fraction of all the products detected,Rotate the solvent to give the product 90.3mg,The yield was 90% and the Dr value was 4: 1.

Statistics shows that 5-Bromo-1-methylindoline-2,3-dione is playing an increasingly important role. we look forward to future research findings about 2058-72-2.

Reference:
Patent; China Pharmaceutical University; Du Ding; Cao Jing; Dong Shuding; (14 pag.)CN106749295; (2017); A;,
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Synthetic Route of 446292-08-6, 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 446292-08-6 as follows.

The reaction flask was charged with 210.7 g (0.5 mol) of the compound prepared in Example 7, (S)-2-{[2-oxo-3-(4-(3-oxorpholine)phenyl)oxazolidin-5-yl]methyl}isoindole-(VII), 1500 ml of absolute ethanol, 500 ml of 30% aqueous methylamine solution, stirred evenly, heated to 40 C to 60 C for 8 hours, TLC in the control (dichloromethane: methanol = 20: 1, volume ratio) reaction is complete, with 10% hydrochloric acid to adjust the pH between 1-2 to precipitate a large number of white solid, cooled to about 15 C, stirring 2 hours, filter. The filter cake was washed with 300 ml of absolute ethanol and dried under reduced pressure to give 147.0 g of a white solid (compound of formula VIII) with a molar yield of 89.7% and an HPLC purity of 98.7%.

According to the analysis of related databases, 446292-08-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Peking University Fangzheng Group Co., Ltd.; Peking University Pharmaceutical Co., Ltd.; Peking University Medical Treatment Industrial Group Co., Ltd.; Xu Hong; Lei Bingying; Zhang Zheng; Wang Wei; Ren Juan; (15 pag.)CN105085370; (2017); B;,
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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 496-12-8 as follows. name: Isoindoline

Example 68A 4-bromophenyl isoindoline-2-carboxylate To a solution of isoindoline (167 mg, 1.401 mmol) and DIEA (0.445 mL, 2.55 mmol) in CH2Cl2 (3 mL), was added 4-bromophenyl carbonochloridate (300 mg, 1.274 mmol). The mixture was stirred at rt for 1 h, then was quenched with water. The mixture was diluted with EtOAc (100 mL), then was washed with 1N HCl, sat Na2CO3 and brine, dried over Na2SO4, and concentrated. The crude product was purified via flash chromatography to afford 310 mg (76%) of Example 68A. MS (ESI) m/z: 318.0 (M+H)+; 1H NMR (500 MHz, CDCl3) delta 7.53-7.48 (m, 2H), 7.36-7.29 (m, 4H), 7.13-7.07 (m, 2H), 4.94 (s, 2H), 4.84 (s, 2H)

According to the analysis of related databases, 496-12-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Glunz, Peter W.; Zou, Yan; Quan, Mimi L.; US2014/206686; (2014); A1;,
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Synthetic Route of 611-09-6, 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 611-09-6 as follows.

General procedure: A mixture of isatin derivatves (1 mmole), malononitrile (1 mmole),1,3-dicarbonyl compounds (1 mmole), and Fe3+-mont. (0.05 g) in CH3CN(5 mL) was heated using an Elmasonic S 40 H ultrasonic cleaning unit at 50 C under silent condition. The progress of the reaction was monitored by TLC (EtOAc/hexane 3:7). After completion of the reaction, the catalyst was removed by filtration. Water was added to the residue. The solid which was obtained was filtered off and dried to provide pure products of the spirooxindole derivatives (4a-j) (Table 3).

According to the analysis of related databases, 611-09-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Mamaghani, Manouchehr; Tabatabaeian, Khalil; Pourshiva, Mina; Nia, Roghayeh Hossein; Journal of Chemical Research; vol. 39; 6; (2015); p. 314 – 317;,
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