Indolines-derivatives

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. 1055412-47-9, name is su-5614, A new synthetic method of this compound is introduced below., Quality Control of su-5614

A suspension of 5-chloro-3-(1H-pyrrol-2-yl-methylene)-1,3-dihydro-indol-2-one (120 mg, 0.44 mmol), morpholine (39 muL, 0.44 mmol) and paraformaldehyde (20 mg, 0.66 mmol) in 8 mL of dioxane and 2 mL of EtOH was heated to 80 C. for 15 h. The reaction mixture was cooled to room temperature and treated with morpholine (25 muL, 0.28 mmol) and paraformaldehyde (16 mg, 0.50 mmol) The reaction mixture was heated at 80 C. for 4 h. The reaction mixture was cooled to room temperature and partially concentrated under a nitrogen stream. The reaction mixture was cooled to -20 C. The solid which formed was collected by filtration and rinsed with EtOH (previously cooled to -20 C.). The solid collected was dried under vacuum to give the title compound (85 mg, 52%) as an orange solid.

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; Allergan, Inc.; US6699863; (2004); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 346-34-9, name is 4-Fluoroindoline-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. Recommanded Product: 4-Fluoroindoline-2,3-dione

General procedure: Compound 2e was prepared from 4-fluoro-1H-indole-2,3-dione 1c and dl-leucine in a similar manner to that described for the synthesis of compound 2a and obtained in 70% yield as a yellow solid. 1H NMR (400 MHz, DMSO-d6) delta 0.85-0.90 (m, 6H), 1.28-1.39 (m, 2H), 1.58-1.67 (m, 1H), 1.92-2.03 (m, 1H), 2.11-2.22 (m, 1H), 2.91-3.04 (m, 1H), 3.15 (s, 3H), 3.38-3.42 (m, 1H), 3.44-3.49 (m, 1H), 6.60-6.69 (m, 2H), 7.15-7.23 (m, 1H), 10.51 (s, 1H). MS m/z 321 (M+H)+.

The synthetic route of 4-Fluoroindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article in Press; Ito, Masahiro; Iwatani, Misa; Yamamoto, Takeshi; Tanaka, Toshio; Kawamoto, Tomohiro; Morishita, Daisuke; Nakanishi, Atsushi; Maezaki, Hironobu; Bioorganic and Medicinal Chemistry; (2017);,
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Electric Literature of 2058-72-2, 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. 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: 30 mg of SiO2_g-C3N4 nanocomposite was dispersed in aqueous media (3 ml) for 30 min and dimedone or 4-hydroxycoumarin (1 mmol), malononitrile (1 mmol) and isatin (1.0 mmol) were added to the mixture. Then, the mixture was stirred at reflux conditions for an appropriate time, while the reaction progress was monitored by thin layer chromatography (TLC). After the reaction was completed, ethyl acetate was employed for the extraction of crude product and the products were dried over anhydrous Na2SO4. The solvent was evaporated followed by recrystallizing of the crude product in hot ethanol, and pure products were identified by IR, 1H and 13C NMR spectral data. The SiO2_g-C3N4 nanocatalyst was washed with EtOH, dried and reused for the next run.

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

Reference:
Article; Allahresani, Ali; Taheri, Bahare; Nasseri, Mohammad Ali; Research on Chemical Intermediates; vol. 44; 2; (2018); p. 1173 – 1188;,
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Electric Literature of 3335-98-6,Some common heterocyclic compound, 3335-98-6, name is 1-Phenyloxindole, molecular formula is C14H11NO, 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: To a Schlenk tube were added indolin-2-one 1 (0.3 mmol), t-BuOOH (0.6 mmol), and DCE (2 mL). Then the tube was stirred at 85 oC under air for the indicated time until complete consumption of starting material monitored by TLC analysis. After the reaction was finished, the reaction mixture was washed with brine. The aqueous phase was re-extracted with ethyl acetate (3×10 mL). The combined organic extracts were dried over Na2SO4, removal of the solvent under vacuum afforded the crude product, which was purified further by column chromatography using hexane-ethyl acetate (10:1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Phenyloxindole, its application will become more common.

Reference:
Article; Ying, Wei-Wei; Zhu, Wen-Ming; Liang, Hongze; Wei, Wen-Ting; Synlett; vol. 29; 2; (2018); p. 215 – 218;,
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. 14192-26-8, name is Methyl 2-oxoindoline-6-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C10H9NO3

Methyl oxindole-6-carboxylate (300.0 g / 1.5691 mol) was suspended in toluene (900.0 ml) at ambient temperature. Chloroacetic anhydride (282.27 ml / 1.494 eq) was added and the suspension was stirred at reflux for 4 hours. The suspension was cooled to ambient temperature, stirred for 30 minutes and the crystalline product filtered off. The crude product was washed with methyl cyclohexane, ice-cold MeOH and Et20 and dried in vacuum to obtain 358.1 g (85.3 %) of l-(2-chloro-acetyl)-2-oxo-2,3-dihydro-lH-indole-6-carboxylic acid methyl ester.

According to the analysis of related databases, 14192-26-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; RATIOPHARM GMBH; TEVA PHARMACEUTICALS USA, INC.; ALBRECHT, Wolfgang; FISCHER, Dirk; JANSSEN, Christian; WO2012/68441; (2012); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. Recommanded Product: 2058-72-2

General procedure: A mixture of corresponding compound 1(0.5 mmol), isatin 3 (0.5 mmol), and sarcosine (0.5 mmol) in acetonitrile (40 mL) (for 1a-c) or in amixture of acetonitrile (30 mL) and chloroform (10 ml) (for 1d-f) was refluxed with stirring for 36 or 72 h for starting compounds 1a-c and 1d-f, respectively. Then the reaction mixture was cooled to room temperature, the precipitate of compounds 4a-e,j,o was filtered off and washed with acetonitrile and water. The reaction mixture of compounds 4f-i,k-n,p-t was concentrated on a rotary evaporator to half of an original volume. After cooling, the precipitate was filtered off and washed with water. Recrystallization from acetonitrile or methanol (4n) gave dispirocompounds 4a-t.

The synthetic route of 5-Bromo-1-methylindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Izmest’ev, Alexei N.; Gazieva, Galina A.; Sigay, Natalya V.; Serkov, Sergei A.; Karnoukhova, Valentina A.; Kachala, Vadim V.; Shashkov, Alexander S.; Zanin, Igor E.; Kravchenko, Angelina N.; Makhova, Nina N.; Beilstein Journal of Organic Chemistry; vol. 12; (2016); p. 2240 – 2249;,
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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. 18711-13-2, name is 4,7-Dichloroindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 4,7-Dichloroindoline-2,3-dione

A. Synthesis of 4,7-dichloro-1-pentyl-1H-indole-2,3-dione To a mixture of sodium hydride (0.17 g, 6.94 mmol, 60% dispersion in mineral oil) in anhydrous N,N-dimethylformamide (5.00 mL) was added a solution of 4,7-dichloro-1H-indole-2,3-dione (1.00 g, 4.60 mmol) in N,N-dimethylformamide (5.00 mL) at 0 C. The brown reaction mixture was stirred for 0.5 h followed by the addition of a solution of 1-bromopentane (0.84 g, 5.55 mmol) in anhydrous N,N-dimethylformamide (5.00 mL). The reaction mixture was stirred at ambient temperature for 16 h and poured into wet ethyl ether (30.0 mL). After the organic layer was separated, it was washed with water (2*20.0 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to dryness. The gummy residue was dried under vacuum and the solid was triturated with ether to give the title compound (0.98 g, 98%): MS (ES+) m/z 286.2 (M+1).

According to the analysis of related databases, 18711-13-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; XENON PHARMACEUTICALS INC.; US2010/173967; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 7147-90-2, name is 5-Chloroisoindoline-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 7147-90-2, COA of Formula: C8H4ClNO2

To a solution of 5-chloro-isoindole-l,3-dione (3.63 g, 20 mmol) in DCM (150 mL) was added methylmagnesium chloride (3 M in THF, 20 mL) dropwise at 0 C. After the addition, the mixture was stirred at 0 C for 3 hours before it was quenched with satd. aq. NH4CI solution. After extraction with DCM, the organic layer was washed with brine, dried over anhy. Na2S04, filtered and concentrated in vacuo to give a crude product containing a mixture of two regioisomers (3.95 g, 100%). MS: 198.1 (M+H+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Chloroisoindoline-1,3-dione, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; AEBI, Johannes; AMREIN, Kurt; CHEN, Wenming; HORNSPERGER, Benoit; KUHN, Bernd; LIU, Yongfu; MAERKI, Hans P.; MAYWEG, Alexander V.; MOHR, Peter; TAN, Xuefei; WANG, Zhanguo; ZHOU, Mingwei; WO2013/79452; (2013); A1;,
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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 32692-19-6 as follows. Formula: C8H8N2O2

General procedure: A solution of 5-nitroindoline (6) (0.5 g, 3.05 mmol) in DMF (10 mL) was treated with NaH (0.39 g, 9.75 mmol, 60% wt in mineral oil) at 0 C resulting in an orange mixture. ;The reaction mixture was then treated with 2-chloro-N,N-dimethylethanamine hydrochloride (0.87 g, 6.09 mmol) resulting in a dark red mixture. ;The reaction was heated to 90 C and stirred for 1.5 h. ;After allowing the reaction to cool to room temperature, water was added and the product was extracted into EtOAc. ;The combined ethyl acetate layer was washed with water, brine and dried (Na2SO4). ;Solvent was evaporated and the crude was purified by flash column chromatography (2 M NH3 in MeOH:CH2Cl2, 2.5:97.5) to obtain the title compound

According to the analysis of related databases, 32692-19-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Annedi, Subhash C.; Maddaford, Shawn P.; Ramnauth, Jailall; Renton, Paul; Rybak, Taras; Silverman, Sarah; Rakhit, Suman; Mladenova, Gabriela; Dove, Peter; Andrews, John S.; Zhang, Dongqin; Porreca, Frank; European Journal of Medicinal Chemistry; vol. 55; (2012); p. 94 – 107,14;; ; Article; Annedi, Subhash C.; Maddaford, Shawn P.; Ramnauth, Jailall; Renton, Paul; Rybak, Taras; Silverman, Sarah; Rakhit, Suman; Mladenova, Gabriela; Dove, Peter; Andrews, John S.; Zhang, Dongqin; Porreca, Frank; European Journal of Medicinal Chemistry; vol. 55; (2012); p. 94 – 107;,
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Indoline | C8H9N – PubChem

15362-40-0, name is 1-(2,6-Dichlorophenyl)-2-indolinone, 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. category: indolines-derivatives

Pyrrole-2-carboxaldehyde (1 mmol) and 1-(2,6-dichlorophenyl)-2-indolinone (1 mmol) were taken in CHCl3 (solvent) and catalytic amount of piperidine (0.2 mmol) was added and then the mixture was subjected to microwave irradiations at 100 C for 1 hr. TLC was used for monitoring the progress of the reaction and after the completion of reaction, it was quenched by adding water. Later the product was extracted with CHCl3 (2 x 50 ml), dried over Na2SO4 and evaporated in vacuum. The crude product was then purified by recrystallization from CHCl3: Methanol (1:3) to get pure product 3e. Yellow Solid, yield 87.2%, mp 178-180 C; IR (KBr): 3469, 3082, 1678, 1597, 1578, 1485; 1H NMR (500 MHz, CDCl3) delta: 6.41-6.43 (m, 1H, ArH), 6.49-6.51 (m, 1H, ArH), 6.85-6.86 (m, 1H, ArH), 7.14-7.21 (m, 3H, ArH), 7.41-7.45 (m, 1H, ArH), 7.56-7.57 (s, 2H, ArH), 7.58 (s, 1H, ArH), 7.61-7.63 (m, 1H, ArH), 13.22 (s, 1H, NH); 13C NMR (125 MHz, CDCl3) delta: 109.0, 111.89, 115.25, 118.2, 121.2, 122.7, 124.9, 125.7, 126.8, 127.3, 128.9, 130.0, 130.7, 135.8, 138.7, 167.2; HRMS (ESI) m/z for C19H12Cl2N2O [M+H]+ calcd. 355.0994, found 355.0326.

The synthetic route of 15362-40-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kaur, Jagroop; Kaur, Baljit; Singh, Palwinder; Bioorganic and Medicinal Chemistry Letters; vol. 28; 2; (2018); p. 129 – 133;,
Indoline – Wikipedia,
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