Author: Jessica.F

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,
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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;,
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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;,
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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;,
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Adding a certain compound to certain chemical reactions, such as: 6326-79-0, name is 6-Bromoisatin, 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 6326-79-0, Application In Synthesis of 6-Bromoisatin

To R27 (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.

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, 6-Bromoisatin, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ANDERSKEWITZ, Ralf; BINDER, Florian; GRAUERT, Matthias; GRUNDL, Marc; HAEBEL, Peter Wilhelm; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; VINTONYAK, Viktor; US2014/275025; (2014); A1;,
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Electric Literature of 99365-40-9,Some common heterocyclic compound, 99365-40-9, name is 6-Bromoindolin-2-one, molecular formula is C8H6BrNO, 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.

a) 6-Bromo-3,3-dimethyl-l,3-dihydro-indol-2-one To a suspension of potassium tert-butylate (12.8 g, 114 mmol) in dry THF (80 ml) at 0C under an argon atmosphere was added portionwise 6-bromoindolin-2-one (5.0 g, 22.9 mmol) followed by copper(I) bromide-dimethylsulfide complex (470 mg, 2.29 mmol). Mel (6.82 g, 3.00 ml, 48.0 mmol) was added dropwise within 45 minutes, keeping temperature of the reaction mixture below 8C. The reaction mixture was warmed to room temperature and kept at this temperature for 16 hours. The reaction mixture was cooled to 0C again and saturated aqueous ammonium chloride solution was cautiously added. The mixture was diluted with tert-butyl methyl ether and water. The aqueous phase was extracted with tert-butyl methyl ether, the combined organic phases were dried over sodium sulfate, the solvent was evaporated and the residue purified by silica gel chromatography using ethyl acetate/ heptane as eluent. The title compound was obtained as light yellow solid (5.17 g). MS ESI (m/z): 240.0/ 242.1 [(M+H)+]. 1H NMR (CDC13, 400 MHz): (ppm) = 8.12 (m, 1H), 7.20-7.16 (m, 1H), 7.09-7.08 (m, 1H), 7.06-7.04 (m, 1H), 1.39 (s, 6H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Bromoindolin-2-one, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BRUNNER, Daniela; MALBERG, Jessica; SHANKAR, Bavani G.; KOLCZEWSKI, Sabine; LIMBERG, Anja; PRINSSEN, Eric; RIEMER, Claus; STOLL, Theodor; WO2014/40969; (2014); A1;,
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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. 40314-06-5, name is 5-Methylisoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C9H7NO2

Isovaleryl chloride (0.50 mL, 4.1 mmol) was added to a mixture of 4-methylphthalimide (0.78 g, 4.8 mmol), triethylamine (0.86 mL, 6.2 mmol), and acetonitrile (8.2 mL) at room temperature and with stirring. After 24 h, the mixture was diluted in EtOAc and washed with satd aq NaHCO3 and brine. The organic phase was dried (MgSO4) and concentrated. The crude material was purified by flash chromatography (SiO2, hexanes:EtOAc 4:1) to give 10 (713 mg, 2.91 mmol, 71%) as a white solid. 1H NMR (300 MHz, CDCl3): delta 7.83 (d, J=7.7Hz, 1H), 7.74 (s, 1H), 7.65 (d, J=7.6Hz, 1H), 2.90 (d, J=6.9Hz, 2H), 2.57 (s, 3H), 2.25 (septet, J=6.7Hz, 1H), and 1.03 (d, J=6.7Hz, 6H). 13C NMR (75 MHz, CDCl3): delta 171.6, 165.6, 165.5, 147.1, 136.2, 131.4, 128.5, 124.6, 124.3, 47.4, 25.0, 22.4, and 22.1. IR (neat): 2956, 1750, 1711, 1612, 1364, 1309, 1109, 1047, and 738 cm-1. HRMS: Calcd for C14H15NNaO3+ [M+Na+] requires 268.0944; found 268.0945. Mp: 180-186 C.

According to the analysis of related databases, 40314-06-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Enright, Robert N.; Grinde, Jeffrey L.; Wurtz, Lincoln I.; Paeth, Matthew S.; Wittman, Tekoa R.; Cliff, Emily R.; Sankari, Yessra T.; Henningsen, Lucas T.; Tan, Chuchen; Scanlon, Joseph D.; Willoughby, Patrick H.; Tetrahedron; vol. 72; 41; (2016); p. 6397 – 6408;,
Indoline – Wikipedia,
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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. 17564-64-6, name is 2-(Chloromethyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C9H6ClNO2

EXAMPLE 1 N-(3,5-di-tert-butyl-4-hydroxyphenylthiomethyl)phthalimide A vessel was charged with 12.19 grams of 3,5-di-tert-butyl-4-hydroxybenzene thiol and 3.30 grams of potassium hydroxide dissolved in 50 ml of acetone and 2 ml of water at 0 C. which was mixed with 10.0 grams of N-(chloromethyl)phthalimide. After stirring for one hour, the precipitated product was removed by filtration and then recrystallized from ethyl acetate-hexane to give 14.9 grams of produt, m.p. 151-53 C. Anal. Calc’d for C23 H27 NO3 S: C, 69.5; H, 6.9; N, 3.5. Found: C, 69.5, H, 7.0, N, 3.6.

According to the analysis of related databases, 17564-64-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ciba-Geigy Corporation; US4692532; (1987); A;,
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Related Products of 6872-06-6, 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. 6872-06-6, name is 2-Methylindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: N-heterocycle substrate (0.2 mmol), Na-AMO (20 mg, 10 mol%), catechol Q-2 (3.3 mg, 0.02 mmol) was added into a reaction tube. The reaction tube was filled and protected with oxygen using a O2 balloon, then H2O was added into the reaction tube with a syringe. The reaction was allowed to react at room temperature for 20 h. After completion of reaction, the resulting mixture was filtered, washed with EtOAc and extracted by EtOAc. The organic phases were combined, washed with brine and dried with Na2SO4. Next, organic solution was concentrated under reduced vacuum to give the crude product. Finally, the product was purified by silica gel chromatography to yield the pure product.

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

Reference:
Article; Tang, Tao; Bi, Xiuru; Meng, Xu; Chen, Gexin; Gou, Mingxia; Liu, Xiang; Zhao, Peiqing; Tetrahedron Letters; vol. 61; 5; (2020);,
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Reference of 6872-06-6, A common heterocyclic compound, 6872-06-6, name is 2-Methylindoline, molecular formula is C9H11N, 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: 2-Methylindoline (400 mg, 3.0 mmol, 1.0 equiv) was dissolved in dry pyridine (10 mL). Methane sulfonyl chloride (480 mg, 4.2 mmol, 1.4 equiv) was added dropwise and the reaction mixture was stirred overnight at rt. Monitoring by HPLC and LCMS indicated that the reaction was completed. The solvent was evaporated under reduced pressure. A solution of HCl 1N (50 mL) and EtOAc (50 mL) were added. The organic layer was separated and the aqueous phase was extracted twice with EtOAc (2×50 mL). The combined organic phase was dried over Na2SO4 and the solvent was evaporated under reduced pressure to yield the pure product: 634 mg, 100 % yield.

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:
Article; Yacovan, Avihai; Ozeri, Rachel; Kehat, Tzofit; Mirilashvili, Sima; Sherman, Daniel; Aizikovich, Alex; Shitrit, Alina; Ben-Zeev, Efrat; Schutz, Nili; Bohana-Kashtan, Osnat; Konson, Alexander; Behar, Vered; Becker, Oren M.; Bioorganic and Medicinal Chemistry Letters; vol. 22; 20; (2012); p. 6460 – 6468;,
Indoline – Wikipedia,
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