Indolines-derivatives

Synthetic Route of 611-09-6, 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. 611-09-6, name is 5-Nitroindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

Intermediate 2 (200 mg, 1.04 mmol), neopentyl glycol (108 mg, 1.04 mmol), p-toluenesulfonic acid (25 mg, 145 mumol) were added to cyclohexane (10 ml), a water separator of the reaction device and a reflux condenser The reaction was refluxed for 16 h. The reaction produced a white solid insoluble in cyclohexane. The reaction was detected by TLC. The solid product was filtered, the solid product was washed with water, dried, and then subjected to silica gel column chromatography (petroleum ether: ethyl acetate = 5: 1). The product was recrystallized from acetonitrile to obtain 243 mg of white needle crystals. Yield: 84%.

The chemical industry reduces the impact on the environment during synthesis 5-Nitroindoline-2,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Shandong University; Zhao Guisen; Zhang Zhen; Zhang Qian; Zhang Jingya; (39 pag.)CN110734391; (2020); A;,
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Synthetic Route of 446292-08-6, 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. 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, it is a common compound, a new synthetic route is introduced below.

2 – ({(5S) -2-oxo-3- [4- (3-oxo-4-morpholinyl) phenyl] -1,3-oxazolidin-5- yl} methyl) -1,3 (2H) -dione (Formula 5) was suspended in 75 ml of ethanol at 22 , and 8.1 g of a methylamine solution (concentration in water of 40%) was added.The reaction mixture was then heated to 60-63 C and stirred at this temperature for 2 hours.After cooling to 55-60 & lt; 0 & gt; C, a total of 14.6 g of a solution of bromic acid (47% in water) was added until the pH was 2.7. After confirming that the crystallization of the product started, the precipitated reaction product was filtered off under suction, washed with methanol, and then dried at 50 DEG C for 4 hours to obtain 7.3 g of the desired product (Yield: 82.6%).

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, (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

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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Some common heterocyclic compound, 205383-87-5, name is tert-Butyl 2-oxospiro[indoline-3,3′-pyrrolidine]-1′-carboxylate, molecular formula is C16H20N2O3, 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 tert-Butyl 2-oxospiro[indoline-3,3′-pyrrolidine]-1′-carboxylate

A mixture containing commercially available tert-butyl 2-oxospiro [indoline-3, 3′-pyrrolidine] -1′-carboxylate (391 mg, 1.36 mmol) and NBS (290 mg, 1.63 mmol) in THF (5 mL) was heated to reflux and stirred for 20 h. The reaction mixture was then cooled, quenched with water, and extracted with EtOAc. The organic layer was concentrated and purified by chromatography on SiO2(2-20MeOH/DCM) to provide tert-butyl 5-bromo-2-oxospiro [indoline-3, 3′-pyrrolidine] -1′-carboxylate. MS (EI) calc’d for C16H20BrN2O3[M+H]+, 367 found, 367.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 205383-87-5, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ACHAB, Abdelghani Abe; CHRISTOPHER, Matthew P.; FRADERA LLINAS, Francesc Xavier; KATZ, Jason D.; METHOT, Joey L.; ZHOU, Hua; XU, Shimin; FU, Jianmin; FU, Ning; LI, Yabin; WANG, Xichao; (228 pag.)WO2017/166104; (2017); A1;,
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These common heterocyclic compound, 39755-95-8, name is 5-Methoxyisatin, 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

General procedure: Fe 3 O 4 /COSbeta-CD-SO 3 H NPs (V) (0.02 g) were added to a mixture of isatin (1 mmol, 0.147 g), 5,5-dimethylcyclohexane-1,3-dione (dimedone) (1 mmol, 0.140g), and malononitrile (1mmol, 0.066g) in water (4mL). The mixture was magnetically stirred at 50C, for 20min. Reaction progress was monitored by TLC (n-hexane:EtOAc, 3:1). Upon reaction completion, the catalyst was removed by an external magnet, washed with water (10mL), and dried overnight to be ready for the next run. The formed solid was filtered off, washed with warm water, then dried to obtain pure products (0.328g, 98%).

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

Reference:
Article; Mohammadian, Narges; Akhlaghinia, Batool; Research on Chemical Intermediates; vol. 45; 10; (2019); p. 4737 – 4756;,
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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. 6326-79-0, name is 6-Bromoisatin belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Product Details of 6326-79-0

For example, Compound 3 (N-benzyl-6-bromoindoline-2,3-dione) was prepared according to Scheme 1a: 6-Bromoisatin (SM1) (984 mg, 4.35 mmol, 1.0 equiv) was dissolved in N,N-dimethylformamide (8.70 mL), and the orange solution was cooled to 0 C. Sodium hydride (183 mg, 4.57 mmol, 60% dispersion in mineral oil, 1.05 equiv) was added in two portions, and the resulting purple suspension was maintained at 0 C. for 15 min. Benzyl bromide (604 muL, 5.05 mmol, 1.16 mmol) was added dropwise, and the resultant orange solution was maintained at 0 C. for 30 min. Water (30 mL) was added, and the biphasic mixture was extracted with EtOAc (4¡Á50 mL). The combined organics were dried over Na2SO4 and concentrated. Purification of the residue by silica gel flash column chromatography (gradient 1:3 EtOAc-hexanes to 100% EtOAc) gave Compound 3 (1.31 g, 95%) as an orange solid: mp 190192 C.; Rf 0.69 (3:7 EtOAc-hexanes); 1H NMR (500 MHz, CDCl3): delta 7.47 (d, J=7.9 Hz, 1H), 7.417.36 (m, 2H), 7.367.31 (m, 3H), 7.287.24 (m, 1H), 6.96 (d, J=1.4, 1H), 4.91 (s, 2H); 13C NMR (125 MHz, CDCl3): delta 182.1 (C), 158.3 (C), 151.6 (C), 134.2 (C), 133.7 (C), 129.4 (CH), 128.6 (CH), 127.6 (CH), 127.3 (CH), 126.5 (CH), 116.5 (C), 114.7 (CH), 44.4 (CH2); IR (film): 1733, 1603 cm1; HRMS-ESI (m/z) [M+Na]+ calcd. for C15H10NO2BrNa, 337.9792; found, 337.9786.

The synthetic route of 6326-79-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Horne, David A.; Jove, Richard; Lincoln, Christopher; Nam, Sangkil; Overman, Larry; Xie, Jun; US2013/225637; (2013); A1;,
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Electric Literature of 2058-74-4, 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 2058-74-4 as follows.

General procedure: To a solution of L-proline-melamine complex (3 mol%) in DMSO (2 mL) was added dimedone 0.025 mg (0.178 mmol), malononitrile (1 equiv) and benzaldehyde / isatin (1 equiv) and stirred at room temperature for 1-20 min. After completion of the reaction (monitored by TLC), ethyl acetate was added stirring and continued for another 5 min. The precipitate formed was filtered. Evaporation of solvent gave the crude product which was recrystallized using ethanol to give the pure compound.

According to the analysis of related databases, 2058-74-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Nagaraju, Sakkani; Paplal, Banoth; Sathish, Kota; Giri, Santanab; Kashinath, Dhurke; Tetrahedron Letters; vol. 58; 44; (2017); p. 4200 – 4204;,
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Synthetic Route of 446292-08-6, 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. 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, it is a common compound, a new synthetic route is introduced below.

42.2g was added to the reaction flask2-[[(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-5-oxazolidinyl]methyl]-1H-isoindole -1,3(2H)-dione,8.6 g of 40% aqueous solution of methylamine and 200 g of absolute ethanol; the temperature was raised to 60 C by stirring, the reaction was kept for 3 hours, the system was cooled to 25 C, 2.8 g of DMTMM was added as a condensing agent, and 17.8 g of 5-chlorothiophene-2-carboxylic acid was dissolved. 35.6g of anhydrous ethanol was added to the system, and the reaction was completed at 25 C for 12 hours. The reaction was completed, and a white solid was obtained by filtration. The mixture was washed with 100 g of anhydrous ethanol and a mixture of water and a mass ratio of 1:1, and filtered to obtain a white solid. Drying at a temperature of 55 C, pressure ? 0.08 MPa for 8 h under reduced pressure, 40.5 g of rivaroxaban dry product (yield: 92.8%; HPLC chiral purity:99.9%),

The synthetic route of (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu Zhongbang Pharmaceutical Co., Ltd.; Wu Siqing; Jiang Haisong; Wang Hongxi; Xu Pengfei; Huang Shuang; (7 pag.)CN108250193; (2018); A;,
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Reference of 60434-13-1, The chemical industry reduces the impact on the environment during synthesis 60434-13-1, name is 5-Chloro-1-methylindoline-2,3-dione, I believe this compound will play a more active role in future production and life.

General procedure: A solution of N-methylisatin (322 mg, 2.0 mmol), phenylacetylene (306 mg, 3.0 mmol), CuI (76 mg, 0.4 mmol), and Cs2CO3 (978 mg, 3.0 mmol) in CH3CN (4.0 mL) was stirred at room temperature for 18 h. After aqueous extractive workup and column chromatographic purification process (CH2Cl2/EtOAc, 15:1) 1a was obtained as a pale yellow solid, 347 mg (66%).1-12 Other compounds were prepared similarly,1-12 and the propargylic alcohols were used in the next hydrogenation step without further identification process.

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-Chloro-1-methylindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Note; Seo, Da Young; Min, Beom Kyu; Roh, Hwa Jung; Kim, Jae Nyoung; Bulletin of the Korean Chemical Society; vol. 38; 10; (2017); p. 1231 – 1234;,
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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. 675109-26-9, name is 6-Bromoisoindolin-1-one, A new synthetic method of this compound is introduced below., COA of Formula: C8H6BrNO

(4) The compound obtained in step (3) (80 g, 0.38 mol) was dissolved in 1 L of dichloromethane.A 1 N solution of borane tetrahydrofuran (1 L) was added dropwise and stirred at room temperature for 4 hours.Then heated to reflux for 3 hours. The system cooled down,100 ml of 2N hydrochloric acid was added dropwise and the mixture was stirred at room temperature for 3 hours and then refluxed for 4 hours. Cooling filtration,The cake was washed with dichloromethane to give an off-white powder that was the target.

The synthetic route of 675109-26-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Xinyuan Pharmaceutical Technology Co., Ltd.; Wu Tianjun; (9 pag.)CN107474006; (2017); A;,
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Electric Literature 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.

General procedure: A mixture of intermediate (3a, 3b, 6a, 6b, 10a, 10b, 11a-d, and14a-g, 1.5 mmol) and methyl (E)-3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate (1.5 mmol) in methanol (10 mL) wasstirred under reflux for 5-10 h. When TLC showed the completionof the reaction, the solution was cooled to room temperature. Theprecipitate was filtered off to give a crude product, which wasrecrystallized from methanol to provide the target compounds.

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:
Article; Qin, Mingze; Tian, Ye; Sun, Xiaoqing; Yu, Simiao; Xia, Juanjuan; Gong, Ping; Zhang, Haotian; Zhao, Yanfang; European Journal of Medicinal Chemistry; vol. 139; (2017); p. 492 – 502;,
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