Indolines-derivatives

Reference of 18711-15-4,Some common heterocyclic compound, 18711-15-4, name is 4,6-Dichloroisatin, molecular formula is C8H3Cl2NO2, 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.

(i) 3-Hydroxy-4,6-dichloro-1,3-dihydro-3-(benzofuran-5-yl)indole-2-one 2.25 g of magnesium for a Grignard reaction in 15 ml of anhydrous THF are placed in a round-bottomed flask equipped with a mechanical stirrer, and under a stream of nitrogen. A mixture of 13.6 g of 5-bromobenzofuran in 35 ml of anhydrous THF is then added. The mixture is stirred for one hour, followed by addition of a solution of 5 g of 4,6-dichloro-1H-indole-2,3-dione in 50 ml of anhydrous THF. The mixture is stirred at room temperature for 4 hours 30 minutes. Water is added and the resulting mixture is extracted with ethyl acetate. The organic phase is separated out, dried over Na2SO4, filtered and evaporated under vacuum. The residue is taken up in ethyl acetate and washed with 1N sodium hydroxide solution. The organic phase is dried over Na2SO4, filtered and evaporated under vacuum. The solid is taken up in ethyl ether and filtered off. 4.2 g of expected product are obtained.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4,6-Dichloroisatin, its application will become more common.

Reference:
Patent; SANOFI; US2011/312972; (2011); A1;,
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Adding a certain compound to certain chemical reactions, such as: 20870-79-5, name is 5-Nitroindolin-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 20870-79-5, Computed Properties of C8H6N2O3

To the mixture of 5-nitro-2-oxindole 2c (0.5g, 0.003mol) and zinc dust (0.91g, 0.014mol) in ethanol (5mL) 2mL of concentrated hydrochloric acid were rapidly added with intensive stirring. After 30min the reaction was terminated by addition of cold water (3mL). Then solid sodium bicarbonate was carefully added to the reaction mixture to adjust pH 8. Solvent was removed in vacuum and crude product was purified by filtering through silica gel pad (eluent MeOH:EtOAc 1:1). After eluent evaporation in vacuum the 5-amino-2-oxindole 2d was obtained as gray powder with yield 79% (0.35g) and used without additional purification. Mp (exp)=190-195C, mp lit34=212-214C). dH (400MHz, DMSO-d6): 3.31 (2H, s, CH2), 4.64, (1H, br s, NH2) 6.39 (1H, dd, J 8.1, 1.3, CHAr), 6.51 (1H, s, CHAr), 6.53 (1H, d, J 7.6, CHAr), 9.99 (1H, s, NH).

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:
Article; Lozinskaya, Natalia A.; Babkov, Denis A.; Zaryanova, Ekaterina V.; Bezsonova, Elena N.; Efremov, Alexander M.; Tsymlyakov, Michael D.; Anikina, Lada V.; Zakharyascheva, Olga Yu.; Borisov, Alexander V.; Perfilova, Valentina N.; Tyurenkov, Ivan N.; Proskurnina, Marina V.; Spasov, Alexander A.; Bioorganic and Medicinal Chemistry; vol. 27; 9; (2019); p. 1804 – 1817;,
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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. 1336963-95-1, name is 6-Bromo-7-fluoroindoline-2,3-dione, A new synthetic method of this compound is introduced below., Product Details of 1336963-95-1

To a solution of 6-bromo-7-fluoroindoline-2,3-dione (1.41 g, 5.80 mmol) in 2 N NaOH (15 mL) was added H202 (30%, 3 mL) at 0C, the mixture was stirred at 0C for 30 mm. After stirring at rt for 16 h, the mixture was poured into ice water, the solution was acidified with Conc. HC1, the precipitate was filtered and dried in the air to afford the desired product as a white solid (1.2 g, 89% 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:
Patent; ARAXES PHARMA LLC; LI, Liansheng; FENG, Jun; LONG, Yun Oliver; LIU, Yuan; WU, Tao; REN, Pingda; LIU, Yi; (246 pag.)WO2017/87528; (2017); 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. 24566-80-1, name is 2-(10-Bromodecyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Quality Control of 2-(10-Bromodecyl)isoindoline-1,3-dione

A 99.0 g amount of 2-(10-bromodecyl)-1H-isoindole-1,3(2H)-dione (prepared as described above) was dissolved in 300 ml of warm N,N-dimethylformamide with stirring. This solution was added to a stirred solution of 1H-imidazole, sodium salt (prepared by stirring a mixture of 20 g of imidazole and 14.0 g 50% sodium hydride in 500 ml of N,N-dimethylformamide at room temperature for 48 hours). The resulting mixture was heated on a steam bath for 14 hours, then taken to dryness in vacuo. The residue was partitioned between 500 ml of dichloromethane and 250 ml of water. The organic layer was washed with 250 ml of water, dried over magnesium sulfate and filter. The filtrate was evaporated in vacuo and gave 85.4 g of 2[10-(1H-imidazol-1-yl)decyl]-1H-isoindole-1,3(2H)dione as an oil which solidified on standing at room temperature.

The synthetic route of 24566-80-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; American Cyanamid Company; US4684654; (1987); A;,
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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 60434-13-1 as follows. HPLC of Formula: C9H6ClNO2

General procedure: To a stirred solution of isatin 6 (20 mmol) in dry DMF (30 mL), K2CO3 (30 mmol) wasadded and stirred for 10 min. 7 (24 mmol) was added dropwise to the reaction mixture. Thereaction mixture was then stirred at room temperature overnight. Ice water was added and theprecipitate produced which was collected by filtration. Orange solid 8 was obtained afterdried by vacuum. Solid 8 was then dissolved in NH2NH2H2O (20 mL) and the reaction mixture washeated to 130 oC. After 3 h, the reaction was cooled and diluted with EtOAc. The aqueouslayer was extracted with EtOAc. The combined organic layer was washed with saturatedaqueous NaHCO3, brine, dried over anhydrous Na2SO4 and concentrated under reducedpressure. The residue 9 was used directly without purified. To a suspension of NaH in THF, N-substitued oxoindole 9 was added by portion in 0 oC.after stirred for 10 minutes, correspond isocyanate was added by potions. The mixture wascontinue stirred overnight. It was quenched by 1M HCl to adjust the PH to 2~5 and thendiluted with EtOAc. The water layer was extracted with EtOAc. The combined organic layerwas washed with water, brine, dried over anhydrous Na2SO4 and concentrated under reducedpressure. The residue was purified by column chromatography on silica gel. (PE/EA = 5/1) togive compound 1a-1r as a white solid.

According to the analysis of related databases, 60434-13-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Chen, Hui; Liu, Hui; Zhao, Si-Han; Cheng, Shao-Bing; Xu, Xiao-Ying; Yuan, Wei-Cheng; Zhang, Xiao-Mei; Synlett; vol. 30; 9; (2019); p. 1067 – 1072;,
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Adding a certain compound to certain chemical reactions, such as: 89-40-7, name is 5-Nitroisoindoline-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 89-40-7, COA of Formula: C8H4N2O4

4-Nitrophthalimide (LOOGR) was taken into a hydrogenation kettle and dissolved using 700ML of dimethylformamide. 5% PALLADIUM/CARBON (LOGR, 50% wet) was added to the solution and hydrogenated initially at 20-30C under 20-40psi. After the exothermic nature of the reaction was over, hydrogen pressure was increased to 40-60psi and the temperature to 40-50C. After the hydrogenation was over the reaction mixture was filtered while hot and the catalyst removed by filtration. Dimethylformamide was removed from the filtrate under reduced pressure at 60-80C. Water (500ML) was added to the residue and the mixture stirred for 30MIN. The product was isolated by filtration and dried at 60-70C to get 80gr (95%) of yellow crystalline solid of 4- aminophthalimide. Melting point: 294-5C.

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

Reference:
Patent; NATCO PHARMA LIMITED; VENKAIAH CHOWDARY, Nannapaneni; WO2004/43919; (2004); 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. 5394-18-3, name is 2-(4-Bromobutyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Computed Properties of C12H12BrNO2

a) A solution of imidazole (13.6 g) in dry DMF (50 ml) was added dropwise to a stirred suspension of sodium hydride (8.0 g, 60% dispersion in oil) in dry DMF (250 ml) at ambient temperature under nitrogen for 2.5 hours. A slurry of N-(4-bromobutyl)phthalimide (53.6 g) in dry DMF (80 ml) was added and the mixture heated at 95 C. for 16 hours. The solvent was evaporated off under vacuum and the residue was extracted with hot toluene. The combined toluene extracts were evaporated to dryness and the residue triturated with ether and dried to give N-[4-(imidazol-1-yl)butyl]phthalimide, m.p. 76-79 C.

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; The Boots Company PLC; US5547972; (1996); A;,
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Reference of 20870-78-4, These common heterocyclic compound, 20870-78-4, name is 5-Bromoindolin-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.

To a solution of commercial available 5-bromoindoline-2-one 2b (425 mg, 2 mmol) and pyrrole 3 (636 mg, 2.4 mmol) in ethanol (4.0 mL) six drops of piperidine were added and the mixture was heated for six hours under reflux. After cooling on ice the precipitate was filtered off, washed with ethanol and dried under vacuum to give 5 (886 mg) as an orange solid in 96% yield, mp: 245-247C, HNMR (d, ppm, DMSO-d): 0.97 (t, 6H, N(CH2CH3)2); 2.43 (s, 3H, CH3); 2.44 (s, 3H, CH3); 2.50 (m, 6H, 3xCH2); 3.29 (m, 2H, NH-CH2); 6.82 (d, 1H, 7-H); 7.25 (d, 1H, 6-H); 7.42 (s, 1H, 4-H); 7.77 (s, 1H, NH-CH2); 8.10 (s, 1H, Hvinyl); 10.99 (s, 1H, NHindole); 13.62 (s, 1H, NHpyrrole); ESI-MS (ES+): m/z=461 (M+H)+

Statistics shows that 5-Bromoindolin-2-one is playing an increasingly important role. we look forward to future research findings about 20870-78-4.

Reference:
Article; Kuchar, Manuela; Oliveira, Maria Cristina; Gano, Lurdes; Santos, Isabel; Kniess, Torsten; Bioorganic and Medicinal Chemistry Letters; vol. 22; 8; (2012); p. 2850 – 2855;,
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Synthetic Route of 552330-86-6,Some common heterocyclic compound, 552330-86-6, name is 5-Bromoisoindolin-1-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.

Intermediate No.175-Bromo-2-(2,2,2-trifluoroethvn-2,3-dihvdro-lH-isoindol-l-one5-Bromo-2,3-dihydro-lH-isoindol-l-one (100 mg, 0.47 mmol) was dissolved inDMF (4.7 mL) and stirred at 0 C. NaH (38 mg, 0.94 mmol, 60% dispersion in oil) was carefully added in two portions, and the resulting mixture was allowed to stir at 0 C for 15 minutes before 2,2,2-trifluoroethyl trifluoromethanesulfonate (110 mg, 0.47 mmol) was added. The mixture was allowed to stir at 0 C for 30 minutes before saturated aqueous NaHC03 (10 mL) was carefully added, and the mixture was extracted with EtOAc. The organic layer was washed with water, brine, dried over anhydrous MgS04, filtered, and concentrated in vacuo. The residue was purified by MPLC on silica gel (using a gradient elution of 0-20% EtOAc/hexanes). Desired fractions were identified, combined, and concentrated in vacuo to afford the title compound. LRMS (ESI) calc’d for C10H7BrF3NO [M+H]+: 294, Found: 294.

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; BRUBAKER, Jason; DINSMORE, Christopher J.; HOFFMAN, Dawn Marie; JUNG, Joon; LIU, Duan; PETERSON, Scott; SIU, Tony; TORRES, Luis E.; ZHANG, Hongjun; WEI, Zhongyong; SHI, Feng; WO2013/40863; (2013); A1;,
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Reference of 20780-72-7, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 20780-72-7 name is 4-Bromoisatin, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: A mixture of 1 (0.4 mmol), 2 (0.4 mmol), Na2CO3 (0.8 mmol) and TBHP (0.4 mmol) in DMF (4 mL) was stirred at rt for 2 h. Then, the mixture was poured into ice-water, acidified with 1 N HCl aq. (6 mL). The mixture was extracted with ethyl acetate (20 mL x 3). The combined organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by silica gel flash column chromatography to give desired products.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromoisatin, and friends who are interested can also refer to it.

Reference:
Article; Wu, Jun; Zhang, Hui; Ding, Xiao; Tan, Xuefei; Shen, Hong C.; Chen, Jie; He, Weimin; Deng, Hongmei; Song, Liping; Cao, Weiguo; Journal of Fluorine Chemistry; vol. 220; (2019); p. 54 – 60;,
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