Category: indolines-derivatives

Electric Literature of 1254319-51-1, 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. 1254319-51-1, name is 6-Bromo-2-methylisoindolin-1-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 6-bromo-2-methylisoindolin-l-one (5 g, 22.1 mmol) in DMF (30 mL) was added bis(pinacolato)diboron (6.18 g, 24.3 mmol) and potassium acetate (6.51 g, 66.4 mmol). The reaction mixture was degassed and backfilled with N2 gas, and l, l’-bis(diphenyl-phosphino)ferrocene palladium(II)dichloride dichloromethane (0.903 g, 1.106 mmol) was added. The reaction mixture was stirred at 80 C for 10 hours. After diluting with EtOAc and water, the organic layer was concentrated and purified on silica column (100% EtOAc) to get the product as a mixture of the title compound as a boronic ester and boronic acid, which was not further purified. MS: 274 (M+1). 1H MR (500 MHz, CDC13): delta 8.33 (s, 1 H), 7.98 (d, 7.5 Hz, 1 H), 7.46 (d, 7.5 Hz, 1 H), 4.41 (s, 2 H), 3.22 (s, 3 H), 1.38 (s, 12 H).

The synthetic route of 6-Bromo-2-methylisoindolin-1-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MSD R&D (CHINA) CO., LTD.; ACTON, John, J., III; BAO, Jianming; DENG, Qiaolin; EGBERTSON, Melissa; FERGUSON, Ronald, III; GAO, Xiaolei; HARRISON, Scott Timothy; KNOWLES, Sandra, L.; LI, Chunsing; LO, Michael Man-Chu; MAZZOLA, Robert, D., Jr.; MENG, Zhaoyang; NA, Meng; RUDD, Michael, T.; SELYUTIN, Oleg, B.; TELLERS, David, M.; TONG, Ling; ZHANG, Fengqi; (195 pag.)WO2019/5587; (2019); A1;,
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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. 3484-35-3, name is 5-Methylindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C9H9NO

General procedure: To a solution of 3-substituted-5-benzylidene-2-thioxo-4-thiazolidinone (1-19) (0.003 mol) in 1,4-dioxane (15 mL) was added HC(OEt)3(2 mL) and BF3Et2O (2 mL). The reaction mixture washeated to 80 C and stirring was continued at the same temperature for 4 h. Theresulting 2-ethylthio-3-substituted-5-benzylidene- 4-thiazolium fluoroborate (Ic, IIc) was precipitated, filteredoff, and dried without any additional purification, as starting material forthe following reactions. To a mixture of thiazolium fluoroborate (Ic, IIc) (0.003 mol) and correspondingindolin-2-one (0.003 mol) in acetonitrile (15 mL) was added triethylamine (0.91g, 0.009 mol) dropwise at 25 C, and the mixture was stirred for 4 h at thesame temperature. The orange precipitate was collected and washed with ethylacetate (8 mL). The crude product thus obtained was recrystallized frommethanol or acetone to give compound (1-19).

According to the analysis of related databases, 3484-35-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wang, Feng; Liu, Zijian; Wang, Jian; Tao, Jun; Gong, Ping; Bao, Xue; Zhao, Yanfang; Wang, Yulin; European Journal of Medicinal Chemistry; vol. 101; (2015); p. 126 – 132;,
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Electric Literature of 496-12-8, These common heterocyclic compound, 496-12-8, name is Isoindoline, 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.

In a 1L round bottom flask were mixed bis(2,5-dioxopyrrolidin-1-yl) carbonate (11.08 g, 43.2 mmol), tert-butyl 4-(4-aminophenyl)piperidine-1-carboxylate (9.96 g, 36.0 mmol), and anhydrous pyridine (2.91 ml, 36.0 mmol) in anhydrous acetonitrile (181 ml). The mixture was stirred overnight at room temperature when DIEA (12.59 ml, 72.1 mmol) was added to the reaction followed by dropwise addition of isoindoline (4.29 g, 36.0 mmol) in anhydrous acetonitrile (20 ml) and anhydrous DMF (10 ml). The solution darkened and then became a suspension after 1-2 h; this mixture was stirred overnight when it was quenched with 300 ml water, stirred vigorously for 1 h and filtered with water washes to give after drying 13.92 g of product as a brown solid.

Statistics shows that Isoindoline is playing an increasingly important role. we look forward to future research findings about 496-12-8.

Reference:
Article; Curtin, Michael L.; Heyman, H. Robin; Clark, Richard F.; Sorensen, Bryan K.; Doherty, George A.; Hansen, T. Matthew; Frey, Robin R.; Sarris, Kathy A.; Aguirre, Ana L.; Shrestha, Anurupa; Tu, Noah; Woller, Kevin; Pliushchev, Marina A.; Sweis, Ramzi F.; Cheng, Min; Wilsbacher, Julie L.; Kovar, Peter J.; Guo, Jun; Cheng, Dong; Longenecker, Kenton L.; Raich, Diana; Korepanova, Alla V.; Soni, Nirupama B.; Algire, Mikkel A.; Richardson, Paul L.; Marin, Violeta L.; Badagnani, Ilaria; Vasudevan, Anil; Buchanan, F. Greg; Maag, David; Chiang, Gary G.; Tse, Chris; Michaelides, Michael R.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 15; (2017); p. 3317 – 3325;,
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Synthetic Route of 3339-73-9, 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. 3339-73-9, name is 3-(1,3-Dioxoisoindolin-2-yl)propanoic acid belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: 1.0 mmol of (1,3-dioxoisoindolin-2-yl) acid, N-ethyl-N-dimethylaminopropylcarbodiimide (EDC) (1.1 mmol), hydroxybenzotriazole(HOBt) (1.2 mmol) and N,N-Diisopropylethylamine (2.0 mmol) weremixed in minimum DMF and the obtained mixture was stirred for5 min. Then, 4-aminoquinoline-diamines (1.0 mmol) was added to thereaction mixture and the stirring was continued for 5 h. The reactionend was proved by thin layer chromatography (TLC). Then, DMF wasevaporated using rotary evaporator and cold water (20 mL) was added,and solid precipitates obtained were filtered and washed with coldwater. The crude product was recrystallized in absolute ethanol.

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-(1,3-Dioxoisoindolin-2-yl)propanoic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Rani, Anu; Legac, Jenny; Rosenthal, Philip J.; Kumar, Vipan; Bioorganic Chemistry; vol. 88; (2019);,
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Some common heterocyclic compound, 480-91-1, name is Isoindolin-1-one, molecular formula is C8H7NO, 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. SDS of cas: 480-91-1

General procedure: Isoindolin-1-one (200 mg, 1.50mmol) was dissolved in super-dry DMSO (4 mL), and Cs2CO3 (1215 mg, 3.75 mmol), CuI (58 mg, 0.30mmol) and N1,N2-dimethylethane-1,2-diamine (27 mg, 33 muL, 0.30 mmol) were added to the solution.The resulting mixture was stirred at room temperature for 10 min, after which iodobenzene (2.25mmol) was added. Then the mixture was heated to 120 C. When TLC showed that isoindolin-1-onehad been fully converted, the reaction was stopped. The mixture was extracted with ethyl acetate (20mL) and H2O (10 mL). The water phase was re-extracted with ethyl acetate (20 mL). The organic layerwas combined and washed with brine (10 mL). Then the solution was dried over anhydrous MgSO4,filtered and concentrated, and the crude residue was purified by flash chromatography over silica gelusing CH2Cl2/CH3OH as the gradient elution to afford the title compounds.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 480-91-1, its application will become more common.

Reference:
Article; Wang, Yixuan; Wang, Huiqiang; Jiang, Xinbei; Jiang, Zhi; Guo, Tingting; Ji, Xingyue; Li, Yanping; Li, Yuhuan; Li, Zhuorong; Molecules; vol. 24; 5; (2019);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 496-12-8, name is Isoindoline, 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 496-12-8, Application In Synthesis of Isoindoline

Example 94 N-[5-(1,3-dihydro-isoindol-2-yl-carbonyl)-1-methyl-pyrrol-3-yl]-4′-trifluoromethyl-biphenyl-2-carboxylic acid amide Prepared analogously to Example 1d from 4-(4′-trifluoromethyl-biphenyl-2-carbonylamino)-1-methyl-pyrrole-2-carboxylic acid, 2,3-dihydro-1H-isoindole, TBTU and N-ethyldiisopropylamine in dimethylformamide. Yield: 79% of theory Rf value: 0.64 (silica gel; dichloromethane/ethanol=9:1)

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, Isoindoline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Boehringer Ingelheim Pharma KG; US2003/162788; (2003); A1;,
Indoline – Wikipedia,
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 6341-92-0 as follows. SDS of cas: 6341-92-0

General procedure: In a 50 mL flask, a mixture of hydrazine hydrate 1 (1 mmol), beta-keto ester 2 (acetylacetic ether or ethyl benzoylacetate) (1 mmol) was stirred at room temperature (78C) for 5 minutes. And then, 2-hydroxynaphthalene-1,4-dione 3 (1 mmol), isatins 4 (1 mmol), MgCl2 (0.1 mmol) and 5 mL ethanol were added to it. The mixture was stirred at 78C for the appropriate time. After completion of the reaction (monitored by TLC), the reaction mixture was cooled to room temperature, 5 mL water was added to it. Then the precipitated products were filtered and washed with cold ethanol (3 mL×2) to afford the pure products as solid powder in good to excellent yields without further purification.

According to the analysis of related databases, 6341-92-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Shen, Tianhua; Fu, Zhijie; Che, Fengfeng; Dang, Haibo; Lin, Yan; Song, Qingbao; Tetrahedron Letters; vol. 56; 9; (2015); p. 1072 – 1075;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 2058-72-2,Some common heterocyclic compound, 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, molecular formula is C9H6BrNO2, 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: Step 1: To a 250 mL flask equipped with a silicone oil bubbler was added commercially available isatin (7.7 g, 50 mmol) and anhydrous DMF (80 mL). the mixture was cooled down to 0 oC. To this solution was added NaH (1.32 g, 55 mmol), followed by the addition of CH3I in 15 min. Upon completion of the reaction (monitored by TLC), the mixture was diluted with saturated NH4Cl solution and extracted with ethyl acetate. The organic layer was washed with water, dried over Na2SO4, filtered, and concentrated to yield the crude N-methylindoline-2, 3-dione, which was used directly in the next step. Step 2: The N-methylindoline-2, 3-dione (7.58 g, 47 mmol) was refluxed in NH2·NH2-H2O ( 35 %) for 1h. Then the mixture was cooled to rt. The crude product was extracted with ethyl acetate. The combined organic layer was then dried over Na2SO4, purified by flash chromatography on silica gel (petroleum ether/ethyl acetate = 10:1). 1-Methylindolin-2-one was obtained as a pink solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-1-methylindoline-2,3-dione, its application will become more common.

Reference:
Article; Zhao, Jian-bo; Ren, Xinfeng; Zheng, Bu-quan; Ji, Jian; Qiu, Zi-bin; Li, Ya; Journal of Fluorine Chemistry; vol. 215; (2018); p. 44 – 51;,
Indoline – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 13220-46-7, name is 4-Methylindolin-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 13220-46-7, category: indolines-derivatives

EXAMPLE 256 4-Methyl-3-[(4-piperidin-1-ylmethyl-phenylamino)-methylene]-1,3-dihydro-indol-2-one. The named compound is prepared by refluxing 0.045 gms E & Z-3-hydroxymethylene-4-methyl-1,3-dihydro-indol-2-one, prepared by substituting 4′-methyl-1,3 dihydro-indol-2-one for 1,3 dihydro-indol-2-one in the reaction of Example 1, with 0.064 gms. 4-piperidin-1-ylmethyl-phenylamine, prepared as in the reaction of Example 251, in tetrahydrofuran (1 mL) overnight. Following cooling to room temperature, solvent evaporation in vacuo, trituration with isopropanol and filtration the reaction yields the named compound as a solid in the amount of 0.0463 gms.

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; Andrews, Steven W.; Wurster, Julie A.; Wang, Edward H.; Malone, Thomas; US2003/199478; (2003); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 24566-80-1, name is 2-(10-Bromodecyl)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. Safety of 2-(10-Bromodecyl)isoindoline-1,3-dione

A mixture of secondary amine from intermediate 1 C (3,6 g, 1 5 ,8 mmol), N-i I 0- ba>mod.ecyl)phthaUmide (4.4 g, 12.0 mmol), (2.0 g, 12.4 mmol) and 2CO3 (8.2 g. 59,4 ramol) in aeetomtrile (90 mL) was stirred at reflux overnight. After filtration, volatile components were evaporated in vacuo. The resulting residue was purified by silica gel column chromatography (5% methanol in dichloromethane) to give the desired phthaltmido- protected i termediate 5b (6.0 g, 86% yield) as a Sight, brown oil, (0272) [0170] Compound 5b (2,9 g, 4.9 mmol) was refluxed with hydrazine hydrate (700 rag, 13.9 mmol in ethanol ( 100 mi.,) for 5 h. The solvent was evaporated and 10% aqueous solution of aOH {20 ml.) was added. The mixture was extracted with CH2CI2. dried over NasSO-t. and evaporated to give the primary amine ;V-(9-( 10-a.minodecy})-9~ (0273) azabkyco[3,3..1 “]nonan-3 -yl)-N -(2-methoxy-5-meihyiphenyl) carbamate 6b (2,2 g, 95% yield) as a Sight yellow oil. NMR (CDC ) 3 7.96 (s, 1H)S 7.14 (s, Eta), 6.72-6,80 (m, 2H), 5.10-5. J 8 (m, 1 H 3.84 (s, 3fl), 3.04-3.07 (m, 2H), 2.65-2.70 (m, 2H), 2.53-2.58 (ra, 2H), 2.39-2.49 (m, 2H), 2.29 (s, 3H>, 2.08-2.20 (in, 1 B), 1 .83- i .94 (ra 2.W). 1.18-1.54 (ra, 23H).

The synthetic route of 2-(10-Bromodecyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WASHINGTON UNIVERSITY; HAWKINS, William; MACH, Robert; SPITZER, Dirk; VANGVERAVONG, Suwanna; (84 pag.)WO2015/153814; (2015); A1;,
Indoline – Wikipedia,
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