Category: 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. 18711-15-4, name is 4,6-Dichloroisatin, A new synthetic method of this compound is introduced below., Application In Synthesis of 4,6-Dichloroisatin

Step 3: Preparation of 2-amino-4,6-dichlorobenzoic acidTo a solution of 4,6-dihloro-lH-indole-2,3-dione (5.0 g, 23.1 mmol) in 75 ml of 1 N NaOH was partially added hydrogen peroxide (28 % v/v, 10 ml) at room temperature. After stirring the mixture for 2 hours, an insoluble dark brown solid was removed by filtration. The filtrate was acidified with a cone, hydrochloric acid to a pH of 2. The yellow precipitate thus formed was harvested, washed with distilled water, and dried in a vacuum. Recrystallization in benzene produced the title compound as an ivory solid (3.90 g, 82%).TLC Rf= 0.1 (ethylacetate : n-hexane = 1:1); m.p. 188 – 189 C;1HNMR (DMSO-de) delta 6.76 (d, IH5J= 1.9 Hz5 ArH), 6.85 (d, IH5J= 1.9 Hz5 ArH);MS(EI) m/e 206 [M+], 162 [M+-CO2].

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; KOREA RESERACH INSTITUTE OF CHEMICAL TECHNOLOGY; WO2008/4716; (2008); A1;,
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Synthetic Route of 6326-79-0, These common heterocyclic compound, 6326-79-0, name is 6-Bromoisatin, 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.

Bis(2-methoxyethyl)aminosulfur trifluoride (deoxo-fluor, 44.25 mL, 22.12 mmol, 50% solution in THF) was added dropwise over 30 min to a suspension of 6-bromoisatin (2.0 g, 8.75 mmol) in DCM (90 mL) at rt with stirring. After 24 h the reaction was cautiously quenched with saturated sodium hydrogen carbonate solution (40 mL) solution at 0 C. The layers were separated and the organics extracts dried (hydrophobic frit/phase separator) and concentrated under reduced pressure. The crude material was purified by silica gel column chromatography eluting with 20% EtOAc in iso-hexane to afford the subtitled compound as an orange solid (1.63 g, 74%). 1H NMR (400 MHz, CH3OH-d4): delta 7.50-7.46 (m, 1H), 7.36 (dd, 1H), 7.18 (d, 1H), (one exchangeable not observed).

The synthetic route of 6326-79-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AstraZeneca AB; Lonn, Hans Roland; Connolly, Stephen; Swallow, Steven; Karlsson, Staffan PO; Aurell, Carl-Johan; Ponten, John Fritiof; Doyle, Kevin James; Van de Poel, Amanda Jane; Jones, Graham Peter; Watson, David Wyn; MacRitchie, Jaqueline Anne; Palmer, Nicholas John; (50 pag.)US9522894; (2016); B2;,
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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 5332-26-3 as follows. Safety of 2-(Bromomethyl)isoindoline-1,3-dione

General procedure: The vacuum dried intermediate 3 (0.002 mol) was then reacted with mono- and di-substituted benzoic acids (0.003 mol) separately in presence of anhydrous potassium carbonate (0.003 mol) in DMF (10 mL). The reaction mixture was stirred at room temperature for about 2 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was poured into ice-cold water and allowed stir for 10 min. The solid obtained was filtered and washed successively with distilled water and recrystallized from ethanol to obtain4(a-n).

According to the analysis of related databases, 5332-26-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kumar, C.S. Chidan; Loh, Wan-Sin; Chandraju, Siddegowda; Win, Yip-Foo; Tan, Weng Kang; Quah, Ching Kheng; Fun, Hoong-Kun; PLoS ONE; vol. 10; 3; (2015);,
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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. 24566-80-1, name is 2-(10-Bromodecyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 2-(10-Bromodecyl)isoindoline-1,3-dione

A suspension of 2-(10-bromodecyl)isoindoline-1,3-dione (190-1) (366 mg, 1 mmol) and thiourea (190-2) (76.1 mg, 1 mmol) in EtOH (1 mL) were heated to 70 C in a glass vial under nitrogen for 3 hours. The solvent was removed and the white solid triturated with ether, filtered, and washed with additional ether to give 2-(10-(1,3-dioxoisoindolin-2-yl)decyl)isothiouronium bromide (190-3) (235 mg, 0.5311 mmol, 53.1 %) as a white powder. LC/MS (ES+): m/z 326.8 [M + H]+

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

Reference:
Patent; C4 THERAPEUTICS, INC.; PHILLIPS, Andrew, J.; NASVESCHUK, Chris, G.; HENDERSON, James, A.; LIANG, Yanke; FITZGERALD, Mark, E.; MICHAEL, Ryan, E.; (790 pag.)WO2017/197056; (2017); A1;,
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Electric Literature of 102359-00-2,Some common heterocyclic compound, 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, molecular formula is C9H7NO3, 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-Oxo-3-(4-oxo-4,5,6,7-tetrahydro-2H-pyrrolo[3,4-c]pyridin-1-ylmethylene)-2,3-dihydro-1H-indole-5-carboxylic acid dimethylamide Benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate (PyBOP, 3.5 g, 6.72 mmol) was added to a mixture of 5-carboxy-2-oxindole (1 g, 5.6 mmol), dimethylamine (5.6 mL of 2.0 M in THF, 11.2 mmol) and triethylamine (2.0 mL, 14 mmol) in dichloromethane. After stirring at room temperature for 3 hours, the reaction was diluted with more dichloromethane, washed with water, saturated sodium bicarbonate and brine, dried and concentrated. The residue was purified by column chromatography to give 480 mg (42%) of 2-oxo-2,3-dihydro-1H-indole-5-carboxylic acid dimethylamide. 1H NMR (300 MHz, DMSO-d6) delta 10.50 (br s, 1H, NH), 7.23 (m, 2H), 6.81 (d, J=6.9 Hz, 1H), 3.49 (s, 2H, CH2), 2.93 (s, 6H, 2xCH3). MS-El m/z 204 [M+].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Oxoindoline-5-carboxylic Acid, its application will become more common.

Reference:
Patent; Tang, Peng Cho; Miller, Todd A.; Li, Xiaoyuan; Zhang, Ruofei; Cui, Jinrong; Huang, Ping; Wei, Chung Chun; US2002/42427; (2002); A1;,
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Application of 897957-06-1, These common heterocyclic compound, 897957-06-1, name is 6-Bromo-1-methylindolin-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.

Step 3: Synthesis of Intermediate R7 To 1-12.2 (32.0 g, 142 mmol) in anhydrous dioxane (400 mL) is added R3 (54.4 g, 241 mmol) and potassium acetate (41.6 g, 424 mmol). The mixture is purged with Argon, [1, – Bis(diphenylphosphino)ferrocene]dichloropalladium(II) as a complex with dichloromethane (11.2 g, 14 mmol) is added and the mixture is heated to 90 C for 2 h. The reaction mixture is diluted with ethyl acetate and water, the organic layer is washed with water, dried over MgS04 and concentrated. The residue is purified via flash chromatography (cyclohexane / EA = 70:30). Yield 72%, m/z 274 [M+H]+, rt 0.67 min, LC-MS Method V011_S01.

Statistics shows that 6-Bromo-1-methylindolin-2-one is playing an increasingly important role. we look forward to future research findings about 897957-06-1.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ANDERSKEWITZ, Ralf; GRAUERT, Matthias; GRUNDL, Marc; HAEBEL, Peter, Wilhelm; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; BINDER, Florian; VINTONYAK, Viktor; WO2014/140075; (2014); A1;,
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Reference of 32372-82-0, These common heterocyclic compound, 32372-82-0, name is Isoindoline hydrochloride, 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.

l-Ethyl-3-(3- dimethylaminopropyl)carbodiimide (2 eq.) was added to a stirred solution of 30 (1 eq.), isoindoline hydrochloride (1.5 eq.), 1- hydroxybenzotriazole (2 eq.) N,N-diisopropylethylamine (2 eq.) in dichloromethane (150 mL) at 0 C. The resulting solution was stirred at room temperature for 14 h before quenching with saturated sodium bicarbonate solution (120 mL). The organic layer was washed with 1 M hydrochloric acid solution (120 mL) and saturated sodium chloride solution (120 mL), dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography (Si02, 1 :4 hexanes/ethyl acetate) to afford 31 (82%) as a white amorphous solid. 1H- NMR (500 MHz, CDC13) delta 8.06 (s, 1H), 7.43 (m, 2H), 7.37 (m, 2H), 5.32 (s, 1H), 5.01 (t, 1H), 4.46 (s, 4H), 3.87 (s, 3H), 3.11 (m, 2H), 2.06 (m, 2H).13C-NMR (125 MHz, CDC13) delta 169.5, 156.6, 143.9, 140.0 (2), 132.8, 129.1, 126.2 (2), 126.2 (2), 115.3, 61.9, 56.1 (2), 35.2, 19.7.

Statistics shows that Isoindoline hydrochloride is playing an increasingly important role. we look forward to future research findings about 32372-82-0.

Reference:
Patent; UNIVERSITY OF KANSAS; BLAGG, Brian S. J.; KENT, Caitlin Nicole; MISHRA, Sanket Jaiprakash; (93 pag.)WO2018/132769; (2018); A1;,
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Synthetic Route of 56341-37-8, 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. 56341-37-8, name is 6-Chlorooxindole belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To the mixture of 6-chloro-2-oxindole (11 g, 65.6 mmol) (Crescent) and 3-chloro-2-fluorobenzaldehyde (12 g, 75.7 mmol) (Aldrich) in methanol (140 mL) was added piperidine (5.59 g, 65.6 mmol) (Aldrich) dropwise. The mixture was then heated at 50 C. for 3 h. After cooled to 4 C., the mixture was filtered and resulting precipitate was collected, dried to give E/Z-6-chloro-3-(3-chloro-2-fluoro-benzylidene)-1,3-dihydro-indol-2-one as a yellow solid (Yield 18 g, 89%).

The synthetic route of 6-Chlorooxindole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bartkovitz, David Joseph; Chu, Xin-Jie; Ding, Qingjie; Graves, Bradford James; Jiang, Nan; Zhang, Jing; Zhang, Zhuming; US2011/130398; (2011); A1;,
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Related Products of 169037-23-4,Some common heterocyclic compound, 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, molecular formula is C9H4F3NO3, 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: A mixture of 5,6-dimethoxy-2-[(E)-1-arylmethylidene]-1-indanone (1, 0.364 mmol), thiazolidine-4-carboxylic (3, 0.364 mmol) and 1-morpholinoindoline-2,3-dione (2,0.364 mmol) was dissolved in methanol (1 mL) and irradiated for 2-3.5 min in a CEM microwave synthesizer (100 0C, 100 W). After completion of the reaction as evident from TLC, the mixture was poured into water. The precipitated solid was filtered and washed with water to afford the products 4a-i which was purified by recrystallisation.

The synthetic route of 169037-23-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Almansour, Abdulrahman I.; Ali, Sadath; Ali, Mohamed Ashraf; Ismail, Rusli; Choon, Tan Soo; Sellappan, Velmurugan; Elumalai, Karthi Keyan; Pandian, Suresh; Bioorganic and Medicinal Chemistry Letters; vol. 22; 24; (2012); p. 7418 – 7421;,
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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. 20780-72-7, name is 4-Bromoisatin belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C8H4BrNO2

General procedure: TiCl4 (0.7 mL, 6 mmol)was added to a stirred suspension of Zn powder (0.78 g, 12 mmol) in freshlydistilled anhydrous THF (15 mL) at room temperature (rt) under a dry N2atmosphere. After completion of the addition, the mixture was refluxed for 2 h.The suspension of the low-valent titanium reagent thus-formed was cooled tort. A solution of isatin or its derivatives 1 or 3 (2 mmol) in THF (10 mL) wasadded dropwise. The mixture was stirred at room temperature for about 5 minunder N2. After this period, the thin layer chromatography (TLC) analysis of themixture showed the reaction completed. The reaction mixture was quenchedwith 3% HCl (15 mL) and extracted with CHCl3 (3 50 mL). The combinedextracts were washed with water (3 50 mL) and dried over anhydrousNa2SO4. After evaporation of the solvent under reduced pressure, the crudeproduct was purified by column chromatography (petroleum ether/ethylacetate = 5:1) to give the pure products 2 or 4.

The synthetic route of 20780-72-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lin, Wei; Hu, Ming-Hua; Feng, Xian; Fu, Lei; Cao, Cheng-Pao; Huang, Zhi-Bin; Shi, Da-Qing; Tetrahedron Letters; vol. 55; 14; (2014); p. 2238 – 2242;,
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