Category: indolines-derivatives

Some common heterocyclic compound, 132898-96-5, name is 2,3-Dioxoindoline-5-sulfonyl chloride, molecular formula is C8H4ClNO4S, 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. Application In Synthesis of 2,3-Dioxoindoline-5-sulfonyl chloride

General procedure: A stirred solution of N-Boc protected pyrrolidine (1.00 mmol) in dry DCM (2.2 mL) at 0 C under argon atmosphere was treated dropwise with TFA (10.00 mmol). Stirring was continued at 0 C for 30 min and at ambient temperature for 2 h. Subsequently, the solution was poured to ice-cooled 10% aq NaOH (15 mL) and extracted with DCM (3 × 15 mL). The combined organic phase was dried over MgSO4 and concentrated in vacuo to obtain a colorless oil as the corresponding unprotected pyrrolidine. After that a solution of the free pyrrolidine and DIPEA (2.00 mmol) in CHCl3 (1.1 mL) was added dropwise to a stirred solution of 5-chlorosulfonyl isatin (1.50 mmol) in CHCl3/THF (1:1, 19 mL) at room temperature. The resulting solution was stirred at room temperature for 1 h and the solvent was completely removed in vacuo. The crude product was purified by flash column chromatography to obtain the corresponding inhibitors.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 132898-96-5, its application will become more common.

Reference:
Article; Limpachayaporn, Panupun; Schaefers, Michael; Schober, Otmar; Kopka, Klaus; Haufe, Guenter; Bioorganic and Medicinal Chemistry; vol. 21; 7; (2013); p. 2025 – 2036;,
Indoline – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-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 2058-72-2, Product Details of 2058-72-2

General procedure: To a solution of carboxylic acid (1.3 mmol) in dry CH3CN (3 mL), were added the isatin derivative (1.00 mmol), cyclohexyl isocyanide (1.0 mmol), and sufficiently activated 4 A MS (100 mg). The resultant mixture was stirred at 80 C for the appropriate time as specified in Table 3 and was monitored by TLC. After completion of the reaction, for compounds 4a-o, the solvent was removed under reduced pressure and the residue dissolved in dry CH2Cl2. The 4 A MS was recovered by simple filtration and addition of n-hexane to the filtrate yielded the pure solid products. For compound 4o, the solvent was removed under reduced pressure and the residue was washed with dry CH2Cl2. The solid residue was then dissolved in EtOH, the 4 A MS was recovered by simple filtration, and the filtrate crystallized from ethanol to yield the pure product 4o in 60% yield.

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; Esmaeili, Abbas Ali; Amini Ghalandarabad, Saeid; Jannati, Saeideh; Tetrahedron Letters; vol. 54; 5; (2013); p. 406 – 408;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 172078-33-0, These common heterocyclic compound, 172078-33-0, name is Indolin-5-ol, 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 one 100mL eggplant-shaped bottle, add 0.54g (4.00mmol) 5-hydroxyindoline, 1.36g (4.16mmol) Cs2CO3 and 30mL absolute ethanol, stir at room temperature for 1h, and 0.79g (3.97mmol) 3a- 1 or 3a-2 and 0.10g (0.60mmol) KI were put into the reaction solution, and the reaction was refluxed at 80 for more than 4h. The progress of the reaction was monitored by thin layer chromatography until the 5-hydroxyindoline point completely disappeared, and vacuum distillation The solvent was removed, and the residue was a pale yellow solid. The residue was dissolved with 30 mL each of water and ethyl acetate. The liquid was separated. The aqueous phase was extracted twice with ethyl acetate, 15 mL each time. The organic phases were combined, washed with water, and washed with saturated brine. Dry over anhydrous sodium sulfate, filter to remove sodium sulfate, the filtrate was distilled under reduced pressure to remove the solvent, the residue was sampled with 100-200 mesh silica gel, and separated by column chromatography (PE:EA=12:1 elution) to give a light yellow oil 4-((Indoline-5-)oxymethyl) benzaldehyde (4d-3, 0.72g, yield 71.29%) or 3-((Indoline-5-)oxymethyl) benzaldehyde (4d-4, 0.77g, yield 76.24%).

The synthetic route of 172078-33-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Chinese People’s Liberation Army Military Academy Of Sciences Military Medical Institute; Wang Liyun; Tong Kun; Shi Weiguo; Cheng Jingchao; Yu Zixing; Ren Fengxia; Zhou Hu; Xiong Ying; (49 pag.)CN111217776; (2020); A;,
Indoline – Wikipedia,
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These common heterocyclic compound, 19155-24-9, name is 3,3-Dimethylindolin-2-one, 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. Formula: C10H11NO

22c. 3,3-dimethylindoline To a solution of 22b (1.0 g, 6.2 mmol) in THF at 0 C. was added LiAlH4 (1M THF solution, 13.6 mL, 2.2 eq) under nitrogen. The resulting slurry was heated at reflux for 4 h. While cooling in an ice bath, sat’d Na2SO4 was added carefully to quench the extra un-reacted LiAlH4. The solids were filtered out, and were rinsed with EtOAc. The organic was washed with H2O, brine, dried over MgSO4, filtered, and concentrated to dryness to give almost pure 22c (0.82 g, yield: 89%). LC-MS ESI 148 (M+H).

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

Reference:
Patent; Tuerdi, Huji; Chao, Hannguang J.; Qiao, Jennifer X.; Wang, Tammy C.; Gungor, Timur; US2005/261244; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 84378-94-9, name is 4-Chloro-5-fluoroindoline-2,3-dione, A new synthetic method of this compound is introduced below., Computed Properties of C8H3ClFNO2

2-amino-5-fluoro-6-chlorobenzoic acid 0.01mol joined is provided with a reflux condenser, magneton, thermometer in three-necked bottle, adding toluene 15 ml, dry SOCl 2 3 ml, reflux 1h, stopping reaction, rotary evaporation under reduced pressure to remove the solvent and redundant SOCl 2. Then added to the flask 0.01moL of 5-fluoro-4-chloro Indoloquinone (5-fluoro-6-chloro Indoloquinone) and 15 ml of dichloromethane, to continue to reflux reaction 1h, cooling to room temperature, filtered, to obtain the yellow solid, washing with methanol, dichloromethane or toluene recrystallization

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; Northwest University; Huo, Baolong; Wang, Cuiling; (52 pag.)CN105330666; (2016); A;,
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Electric Literature of 6326-79-0, 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. 6326-79-0, name is 6-Bromoisatin, This compound has unique chemical properties. The synthetic route is as follows.

To R7 (25.0 g, 111 mmol) in acetonitrile (750 mL) is added MeI (15 mL, 241 mmol) and K2CO3 (60.0 g, 434 mmol) and the reaction mixture is stirred at 60 C. for 2 h. The reaction mixture is filtered and concentrated. Water and ethyl acetate are added to the residue. The organic layer is extracted twice with water, dried over MgSO4 and concentrated. Yield 56%, m/z 240/242 [M+H]+, rt 0.48 min, LC-MS Method X001-004.

The chemical industry reduces the impact on the environment during synthesis 6-Bromoisatin. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GRAUERT, Matthias; ANDERSKEWITZ, Ralf; GRUNDL, Marc; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; US2014/275155; (2014); A1;,
Indoline – Wikipedia,
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Reference of 496-12-8, 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. 496-12-8, name is Isoindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: In an oven-dried RB flask, 4-chloro-2-phenyl-1H-pyrrolo[3,2-c]pyridine 6b (250 mg, 1.09 mmol) and formaldehyde solution, 37 wt.% in H2O (0.2 mL, 2.73 mmol) were mixed in glacial acetic acid(5 mL). N-methyl piperazine (273.8 mg, 2.73 mmol, CAS 109-01-3)was added drop wise at 0C. The resulting mixture was stirred atroom temperature for 12 h. After completion of the reaction, the excess solvent was evaporated to dryness under reduced pressure.The residue was neutralized with 10% NaHCO3 solution, the solidf ormed was collected by filtration, washed with water and dried.The crude product was purified by silica gel column chromatographyto provide title compound as an off-white solid (326.3 mg,88%).

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

Reference:
Article; Jose, Gilish; Suresha Kumara, Tholappanavara H.; Sowmya, Haliwana B.V.; Sriram, Dharmarajan; Guru Row, Tayur N.; Hosamani, Amar A.; More, Sunil S.; Janardhan, Bhavya; Harish; Telkar, Sandeep; Ravikumar, Yalegara Siddappa; European Journal of Medicinal Chemistry; vol. 131; (2017); p. 275 – 288;,
Indoline – Wikipedia,
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Application of 56341-37-8, A common heterocyclic compound, 56341-37-8, name is 6-Chlorooxindole, molecular formula is C8H6ClNO, 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.

EXAMPLE 61a 4-(6-Chloro-2-oxo-1,2-dihydro-indol-3-ylidene)-azepane-1-carboxylic acid tert-butyl ester A suspension of 6-chlorooxindole (0.71 g, 4.24 mmol) (Cresent Chem.), (3-oxo-butyl)-propyl-carbamic acid tert-butyl ester (1 g, 4.69 mmol) (Tyger Sci.), and pyrrolidine (0.1 g) (Aldrich) in 2-propanol (15 mL) was heated at 90 C. for 2 days. The mixture was allowed to cool to room temperature. The solvent was removed and the residue was purified by chromatography to give 4-(6-chloro-2-oxo-1,2-dihydro-indol-3-ylidene)-azepane-1-carboxylic acid tert-butyl ester as a brown solid. (Yield: 1.36 g, 88%).

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; Luk, Kim-Chun; So, Sung-Sau; Zhang, Jing; Zhang, Zhuming; US2006/293319; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 3484-35-3, 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.

General procedure: A reaction mixture of compound 19-21 (2.35 mmol),compound 14-18 (2.14 mmol) and 2 drops of piperidine was stirred at RT for 3 h. The precipitate was filtered off and dried. The crude compound was purified by column chromatography using ethyl acetate in dichloromethane (13%) to afford the desired products (4, 22-32).

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

Reference:
Article; Dai, Hou-Ling; Gao, Li-Xin; Yang, Ying; Li, Jing-Ya; Cheng, Jia-Gao; Li, Jia; Wen, Ren; Peng, Yan-Qing; Zheng, Jian-Bin; Bioorganic and Medicinal Chemistry Letters; vol. 22; 24; (2012); p. 7440 – 7443;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 435273-55-5,Some common heterocyclic compound, 435273-55-5, name is 4-Bromo-2-methylisoindolin-1-one, molecular formula is C9H8BrNO, 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.

2-methyl-l-oxoisoindoline-4-carbaldehyde: To a solution of 4-bromo-2- methylisoindolin-l-one (200mg, 0.89 mmol) in THF (3 mL), n-BuLi (0.78 mL, 1.95 mmol) was added to the solution at -78 C. After 30 minutes, DMF (0.273 mL, 3.57 mmol) was added to the solution. After 1 hour, the reaction was warmed up. Diluted with EtOAc and washed with brine. The organic layer was dried over sodium sulfate, and concentrated. The product was purified by chromatography on silica gel (eluent: EtOAc/hexanes) to yield the product after lyophilization from water / MeCN.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-2-methylisoindolin-1-one, its application will become more common.

Reference:
Patent; GILEAD SCIENCES, INC.; BACON, Elizabeth, M.; BALAN, Gayatri; CHOU, Chien-Hung; CLARK, Christopher, T.; COTTELL, Jeromy, J.; KIM, Musong; KIRSCHBERG, Thorsten, A.; LINK, John, O.; PHILLIPS, Gary; SCHROEDER, Scott, D.; SQUIRES, Neil, H.; STEVENS, Kirk, L.; TAYLOR, James, G.; WATKINS, William, J.; WRIGHT, Nathan, E.; ZIPFEL, Sheila, M.; (604 pag.)WO2017/7689; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem