Category: indolines-derivatives

Application of 611-09-6, A common heterocyclic compound, 611-09-6, name is 5-Nitroindoline-2,3-dione, molecular formula is C8H4N2O4, 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: A mixture of malononitrile (1 mmol), isatin (1 mmol), dicarbonyl (1 mmol), PEGOSO3H(0.1 mmol), and water (2 mL) was stirred under reflux for the appropriate time (shown in Tables 3, 4). After completion of the reaction, the reaction mixture was filtered and the residue was washed with ethanol. The crude solid product was recrystallized from EtOH to afforded the pure products in high purity and yield.Assignment of the structures of the products was based on their 1H NMR, 13C NMR,and IR spectra.

The synthetic route of 611-09-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nasseri; Zakerinasab; Research on Chemical Intermediates; vol. 41; 8; (2015); p. 5261 – 5270;,
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Some common heterocyclic compound, 6941-75-9, name is 5-Bromoisoindoline-1,3-dione, molecular formula is C8H4BrNO2, 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. name: 5-Bromoisoindoline-1,3-dione

5-Bromophthalimide (1.76 g, 7.8 mmol) was dissolved in abs. ethanol (75 ml), the mixture was heated to 60 C. and an aqueous solution of potassium hydroxide (4 ml, 10.5 mmol) was added dropwise. After 30 min of stirring at 60 C., the reaction mixture was cooled quickly with the aid of an ice bath, and the resulting precipitated colourless solid was filtered off with suction, washed with cold ethanol and dried under reduced pressure. In this manner, potassium 5-bromophthalimidate (1.04 g, 50% of theory) were obtained in the form of a colourless solid. 1H-NMR (400 MHz, d6-DMSO delta, ppm) 7.59 (dd, 1H), 7.45 (d, 1H), 7.29 (d, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6941-75-9, its application will become more common.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GmbH; Frackenpohl, Jens; Zeiss, Hans-Joachim; Heinemann, Ines; Willms, Lothar; Mueller, Thomas; Busch, Marco; Von Koskull-Doeering, Pascal; Rosinger, Christopher Hugh; Dittgen, Jan; Hills, Martin Jeffrey; US2014/302987; (2014); A1;,
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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. 1168150-46-6, name is (E)-Methyl 3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: 1168150-46-6

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 1168150-46-6 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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Application of 550-44-7, A common heterocyclic compound, 550-44-7, name is 2-Methylisoindoline-1,3-dione, molecular formula is C9H7NO2, 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.

To a suspension of LiAlH4 (1.1403 g) in dry THF (24 ml) under argonatmosphere, a solution of MeOH (2 ml) in THF (24 ml) was added over 16 min at 0C,followed by cooling of the whole to -74C (in an acetone-dry ice bath). To thissuspension, N-methylphthalimide 13 (1.6177 g, 10.0 mmol) was added in portions at-74C, and the mixture was stirred at this temperature for 40 min. Then the mixture was stirred at 0C for 45 min. A saturated aqueous solution of sodium sulfate (8 ml) wasadded, and the resultant inorganic salt was filtered by suction, and the precipitate waswashed with acetone. The combined organic layer was dried over magnesium sulfate,and the organic solvent was evaporated at 30C to give the residue 14 (yellow solid,1.1544 g, 88% yield). This intermediate is rather unstable, and it was used with furtherpurification. 1H-NMR (CDCl3): delta = 7.500 (2H, m), 7.040 (2H, s), 6.904 (2H, m), 3.987(3H, s).

The synthetic route of 550-44-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kozai, Daisuke; Kabasawa, Yoji; Ebert, Maximilian; Kiyonaka, Shigeki; Firman; Otani, Yuko; Numata, Tomohiro; Takahashi, Nobuaki; Mori, Yasuo; Ohwada, Tomohiko; Molecular Pharmacology; vol. 85; 1; (2014); p. 175 – 185;,
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Adding a certain compound to certain chemical reactions, such as: 1035235-27-8, name is tert-Butyl 4-bromoisoindoline-2-carboxylate, 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 1035235-27-8, SDS of cas: 1035235-27-8

Carbon dioxide (g, 60 atm) was introduced into a lOO-mL pressure tank reactor containing a solution of tert-butyl 4-bromo-2,3-dihydro-lH-isoindole-2-carboxylate (2.00 g, 6.71 mmol), triethylamine (2.80 mL, 20.1 mmol), and [l,l?-bis(diphenylphosphino)ferrocene]- dichloropalladium (II), complex with dichloromethane (820 mg, 1.12 mmol) in ethanol (50 mL). The resulting mixture stirred overnight at 120 C. The reaction was concentrated under vacuum and then quenched by the addition of 50 mL of water. The resulting solution was extracted with 3×50 mL of ethyl acetate, washed with 100 mL of brine, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified via column chromatography on silica gel (eluting with ethyl acetate/petroleum ether (1 : 10)) to afford 2-(tert-butyl) 4-ethyl isoindoline-2,4-dicarboxylate (1.67 g, 85%) as an off-white solid. MS: (ESI, m/z): 292[M+H]+

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; FORMA THERAPEUTICS, INC.; ZHENG, Xiaozhang; MARTIN, Matthew W.; NG, Pui Yee; THOMASON, Jennifer R.; HAN, Bingsong; RUDNITSKAYA, Aleksandra; LANCIA, JR., David R.; (180 pag.)WO2019/204550; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 21857-45-4, A common heterocyclic compound, 21857-45-4, name is 5-Methoxyindoline, molecular formula is C9H11NO, 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.

To a 100 mL round- bottomed flask, flushed with nitrogen, were added 17 (91 mg, 0.5 mmol), 5-methoxyindoline (82 mg, 0.55 mmol), BuOH (10 mL), and 2-3 drops of cone. HC1. The reaction mixture was heated at reflux with stirring for 12 h until the starting material 17 disappeared (TLC). The reaction solution was allowed to cool to room temperature; the solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel with hexane: acetyl acetate = 20: 1 as the eluent. Fractions containing the product (TLC) were combined and evaporated to afford 93 mg (63%) 8 as a white powder: mp 201.1-202.3 C; Rf 0.5 (AcOEt/Hexane 3 : 1); 1H NMR (DMSO-d6) delta 2.42 (s, 3 H), 2.53 (s, 3 H), 3.25 (t, 2 H), 3.75 (s, 3 H), 4.39 (t, 2 H), 6.79 (t, 2 H), 6.89 (d, 1 H), 8.48 (d, 1 H), Anal. Ci7H17N302

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; DUQUESNE UNIVERSITY OF THE HOLY SPIRIT; GANGJEE, Aleem; (111 pag.)WO2016/100495; (2016); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 603-62-3, 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 603-62-3 as follows.

Step 1: To a solution of potassium hydroxide (16.1 g, 286 mmol) in water (500 mL), was added 3-nitrophthalimide (25.0 g, 130 mmol) in portion at 0 C. The suspension was stirred at 0 C. for 3 hrs, and then heated to 30 C. for 3 hrs. To the solution, was added HCl (100 mL, 6N). The resulting suspension was cooled to 0 C. for 1 hr. The suspension was filtered and washed with cold water (2*10 mL) to give 3-nitro-phthalamic acid as a white solid (24.6 g, 90% yield): 1H NMR (DMSO-d6) delta 7.69 (brs, 1H, NHH), 7.74 (t, J=8 Hz, 1H, Ar), 7.92 (dd, J=1, 8 Hz, 1H, Ar), 8.13 (dd, J=1, 8 Hz, 1H, Ar), 8.15 (brs, 1H, NHH), 13.59 (s, 1H, OH); 13C NMR (DMSO-d6) delta 125.33, 129.15, 130.25, 132.54, 136.72, 147.03, 165.90, 167.31.

According to the analysis of related databases, 603-62-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Muller, George W.; Schafer, Peter H.; Man, Hon-Wah; Zhang, Ling-Hua; Gandhi, Anita; Chopra, Rajesh; US2012/230983; (2012); A1;,
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Synthetic Route of 2436-29-5,Some common heterocyclic compound, 2436-29-5, name is 3-(1,3-Dioxoisoindolin-2-yl)propanal, molecular formula is C11H9NO3, 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.

3-(1,3-Dioxoisoindolin-2-yl)propanal (2.5 g, 12.3 mmol) was dissolved in 80 mL of DCM. (1ethoxycarbonylethylidene)triphenylphosphorane (4.50 g, 12.9 mmol) was added thereto, and the mixtue was stirred at room temperaturefor 2 hours. The reaction solution was concentrated under reduced pressure and purified by column chromatography toobtain the title compound (2.99 g, 89 %).1H-NMR (CDCl3) delta7.83 (2H, m), 7.72 (2H, m), 6.91 (1H, m), 5.90 (1H, d), 4.16 (2H, q), 3.83 (2H, t), 2.60 (2H, m), 1.26 (3H, t)

The synthetic route of 2436-29-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LG Chem, Ltd.; KIM, Young Kwan; PARK, Sang Yun; JOO, Hyun Woo; CHOI, Eun Sil; PAEK, Seung Yup; KANG, Seung Wan; KIM, Byung Gyu; LEE, Chang Seok; KIM, Sung Wook; LEE, Sang Dae; (369 pag.)EP3239143; (2017); A2;,
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Reference of 102359-00-2, A common heterocyclic compound, 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, molecular formula is C9H7NO3, 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.

1-[2-Oxo-5-(pyrrolidine-1-carbonyl)-1,2-dihydro-indol-3-ylidenemethyl]-2,5,6,7-tetrahydro-pyrrolo[3,4-c]pyridin-4-one PyBOP (3.5 g, 6.72 mmol) was added to a mixture of 5-carboxy-2-oxindole (1 g, 5.6 mmol), pyrrolidine (0.5 mL, 6.2 mmol) and triethylamine (2.0 mL, 14 mmol) in dichloromethane. After stirring at room temperature for 4 hours, the reaction was diluted with more dichloromethane, washed with saturated sodium bicarbonate and brine, dried and concentrated. The residue was purified by column chromatography to give 5-(pyrrolidine-1-carbonyl)-1,3-dihydro-indol-2-one. 1H NMR (300 MHz, DMSO-d6) delta 10.52 (br s, 1H, NH), 7.37 (m, 2H), 6.80 (d, J=8.5 Hz, 1H), 3.49 (s, 2H, CH2), 3.42 (m, 4H, 2xCH2), 1.81 (m, 4H, 2*CH2). MS-El m/z 230 [M+].

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; Tang, Peng Cho; Miller, Todd A.; Li, Xiaoyuan; Zhang, Ruofei; Cui, Jinrong; Huang, Ping; Wei, Chung Chun; US2002/42427; (2002); A1;,
Indoline – Wikipedia,
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Related Products of 2058-72-2, 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.

General procedure: A solution of isatins 1 (0.6 mmol), 3-methyl-4-nitro-5-isatylidenylisoxazoles 2 (0.4 mmol) and proline or thioproline (0.8 mmol) in the 10.0 mL of EtOH at reflux for 5 h. After completion of the reaction, as indicated by TLC, the reaction mixture was directly subjected to flash column chromatography on silica gel (petroleum ether/EtOAc = 5:1-3:1) to furnish the corresponding products 3.

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; Lin, Bing; Zhang, Wen-Hui; Wang, Dan-Dan; Gong, Yi; Wei, Qi-Di; Liu, Xiong-Li; Feng, Ting-Ting; Zhou, Ying; Yuan, Wei-Cheng; Tetrahedron; vol. 73; 34; (2017); p. 5176 – 5188;,
Indoline – Wikipedia,
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