Indolines-derivatives

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 24566-79-8 as follows. Computed Properties of C14H16BrNO2

To a stirred solution of compound 3-i (6.39 g, 20.3 mol) in DMF (60 mL) was added potassium thioacetate (2.78 g, 34.3 mmol) portion wise and stirred for 20 mm at room temperature. After complete addition, the reaction mixture was stirred at room temperature for 30 mm. Reaction progress was monitored by TLC; after completion the reaction mixture was quenched with ice-cold water (250 mL) and stirred for 1 h. The resultant precipitated was filtered, washed with water (100 mL) and dried in vacuo to afford 4-i as an off-white solid(5.8 g, 93.5%). LCMS: 306.20 (M+1).

According to the analysis of related databases, 24566-79-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CV6 THERAPEUTICS (NI) LIMITED; SPYVEE, Mark; LADNER, Robert, D.; (340 pag.)WO2018/98207; (2018); A1;,
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Reference of 20870-90-0, 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. 20870-90-0, name is 5-Bromo-1-methyl-2-oxoindoline, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a precooled stirring suspension of NaH (6.0 mmol, 0.144 g) in THF (10 mL) at -78 C was added a solution of N-methyloxindole (5a) (6.0 mmol, 0.883 g) in THF (10 mL) dropwise. Then the cooling bath was removed and stirring continued for 5 min (till the formation of clear solution). Then the reaction mixture was again cooled to -78 C and a solution of methyl 3-hydroxy-2-methylene-3-phenylpropanoate (6a) (2.0 mmol, 0.468 g) in THF (15 mL) was added dropwise over 30 min. After stirring for further 10 min at the same temperature, the cooling bath was removed and the reaction was quenched with saturated NH4Cl solution and extracted with EtOAc (3¡Á30 mL). Combined organic layer was dried over anhydrous Na2SO4.. Solvent was removed and the crude obtained was purified by column chromatography(10-15% EtOAc in hexanes) provided title compound (7a) (0.539 g) as a colorless solid in 84% yield.

The chemical industry reduces the impact on the environment during synthesis 5-Bromo-1-methyl-2-oxoindoline. I believe this compound will play a more active role in future production and life.

Reference:
Article; Basavaiah, Deevi; Lingam, Harathi; Babu, Thelagathoti Hari; Tetrahedron; vol. 74; 19; (2018); p. 2306 – 2313;,
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201940-08-1, name is tert-Butyl 5-bromoisoindoline-2-carboxylate, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Quality Control of tert-Butyl 5-bromoisoindoline-2-carboxylate

0.69 ml of n-Butyl lithium (2.5M solution in hexane) was added dropwise to a stirred solution of 5- bromo-1 ,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester (429 mg; 1.44 mmol) in anhydrous THF (10 ml) at -780C under an atmosphere of nitrogen. The reaction was stirred for 50 minutes then 1-methyl-4-piperidone (212 mul; 1.2 equiv.) was added and stirred at -780C for a further 60 minutes then warmed to room temperature. The reaction was quenched with saturated ammonium chloride solution then extracted with EtOAc. The EtOAc layer was washed with saturated NaHCO3, brine, dried (MgSO4) and evaporated. Purification by flash column chromatography on SiO2, gradient elution from 0% to 10% 2M methanolic ammonia / DCM gave 111 mg of 5-(4-hydroxy-1-methyl- piperidin-4-yl)-1 ,3-dihydro-isoindole-2-carboxylic acid tert-butyi ester as a colourless oil.

The synthetic route of 201940-08-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; WO2008/44041; (2008); A1;,
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Some common heterocyclic compound, 32692-19-6, name is 5-Nitroindoline, molecular formula is C8H8N2O2, 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. Computed Properties of C8H8N2O2

Reference Example 49 7-bromo-5-nitro-1H-indoline 5-nitro-1H-indoline (2.0 g) was dissolved in acetic acid (15.0 mL), bromine (1.0 mL) was added, and the mixture was stirred at room temperature for 3 hours. The reaction mixture was poured into ice water, and this was neutralized with a 1 mol/L aqueous sodium hydroxide solution. The produced crystal was filtered and washed with water, and the resulting crystal was then dried under reduced pressure to obtain the title compound (3.3 g). 1H NMR (CDCl3) delta (ppm): 3.27(2H,t), 3.86(2H,t), 7.90(1H,s), 8.19(1H,s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 32692-19-6, its application will become more common.

Reference:
Patent; Sanwa Kagaku Kenkyusho Co., Ltd; EP2036887; (2009); A1;,
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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 366452-98-4 as follows. Safety of 4-Amino-2,3-dihydro-1H-isoindol-1-one

l Synthesis of isoindolinone (25): The suspension of 2,3-dihydro-1H-isoindol-1-one 4 (0.100 gm, 0.61 mmol.) in ethyl acetate and aq. NaHCO3 solution, was added m-nitrobenzoyl chloride (0.15 mg, 0.81 mmol.) at room temperature. The reaction mixture was stirred at room temperature for 30 min, and solid separated was filtered and dried under vacuum to give 2,3-dihydro-1H-isoindol-1-one 25 (0.041 gm, 36%).

According to the analysis of related databases, 366452-98-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Jagtap, Prakash; Southan, Garry; Salzman, Andrew; Szabo, Csaba; Ram, Siya; US2002/95044; (2002); A1;,
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Reference of 20870-78-4,Some common heterocyclic compound, 20870-78-4, name is 5-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.

5-Bromo-2-oxindole (10 g, 47 mmol), 7.4 g (61 mmol) of benzeneboronic acid, 4.0 g (3.5 mmol) of tetrakis(triphenylphosphine)palladium(0), 17 g (160 mmol) of anhydrous sodium carbonate, 100 mL of toluene and 100 mL of ethanol were refluxed for 18 hours. The mixture was vacuum filtered hot to remove insolubles. The organic layer of the filtrate was separated while hot and concentrated. The solids were collected by vacuum filtration and washed with 5 mL of ethanol. The solids were triturated with 1 N hydrochloric acid, collected by vacuum filtration, washed with water and dried under vacuum. The crude solids were triturated with dichloromethane and dried under vacuum to give 8.3 g (63% yield) of the title compound. 1H-NMR (dimethylsulfoxide-d6) delta10.00 (s, 1H), 7.20-6.80 (multiplets, 9H), 3.50 (s, 3H).

The synthetic route of 20870-78-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUGEN, Inc.; US2004/186160; (2004); A1;,
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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 2058-74-4 as follows. name: 1-Methylisatin

General procedure: A solution of N-methylisatin (322 mg, 2.0 mmol), phenylacetylene (306 mg, 3.0 mmol), CuI (76 mg, 0.4 mmol), and Cs2CO3 (978 mg, 3.0 mmol) in CH3CN (4.0 mL) was stirred at room temperature for 18 h. After aqueous extractive workup and column chromatographic purification process (CH2Cl2/EtOAc, 15:1) 1a was obtained as a pale yellow solid, 347 mg (66%).1-12 Other compounds were prepared similarly,1-12 and the propargylic alcohols were used in the next hydrogenation step without further identification process.

According to the analysis of related databases, 2058-74-4, the application of this compound in the production field has become more and more popular.

Reference:
Note; Seo, Da Young; Min, Beom Kyu; Roh, Hwa Jung; Kim, Jae Nyoung; Bulletin of the Korean Chemical Society; vol. 38; 10; (2017); p. 1231 – 1234;,
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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. 59-48-3, name is Indolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C8H7NO

5-Iodo-2-oxindole 2-Oxindole (82.9 g) was suspended in 630 mL of acetic acid with mechanical stirring and the mixture cooled to 10 C. in an ice water bath. Solid N-iodosuccinimide (175 g) was added in portions over 10 minutes. After the addition was complete the mixture was stirred for 1.0 hour at 10 C. The suspended solid, which had always been present, became very thick at this time. The solid was collected by vacuum filtration, washed with 100 mL of 50% acetic acid in water and then with 200 mL of water and sucked dry for 20 minutes in the funnel. The product was dried under vacuum to give 93.5 g (36%) of 5-iodo-2-oxindole containing about 5% 2-oxindole by proton NMR.

The synthetic route of 59-48-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sugen, Inc.; US6878733; (2005); B1;,
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Electric Literature of 64483-69-8, 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. 64483-69-8, name is 5-Acetylindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 40 A solution of 5-acetyloxindole (352 mg, 2 mmol), (EP 0155828 A2), in DMF (5 ml) was added to a suspension of sodium hydride (80 mg, 2 mmol, prewashed with hexane) in DMF (1 ml) and the mixture stirred for 30 minutes at ambient temperature. 4-Chloro-6-methoxy-7-(2-methoxyethoxy)quinazoline (180 mg, 0.67 mmol), (prepared as described for the starting material in Example 2), was added and the mixture was heated at 50 C. for 1.5 hours. The mixture was partitioned between water and ether and the aqueous layer was adjusted to pH7 with 2M hydrochloric acid. The precipitate was collected by filtration, washed with water and dried under vacuum. The solid was dissolved in methylene chloride/methanol (30 ml/30 ml) and 7M ethanolic hydrogen chloride (1 ml) was added. The mixture was left to stand for 15 minutes at ambient temperature, the resulting precipitate was collected by filtration, washed with ether and dried under vacuum to give 4-(5-acetyloxindol-3-yl)-6-methoxy-7-(2-methoxyethoxy)quinazoline hydrochloride (195 mg, 71%). 1H NMR Spectrum: (DMSOd6, CF3CO2D) 2.52(s, 3H); 3.37(s, 3H); 3.80(t, 2H); 3.85(s, 1H); 4.35(t, 2H); 7.09(d, 1H); 7.33(s, 1H); 7.78(s, 1H); 7.88(d, 1H); 8.25(s, 1H); 8.85(s, 1H). MS-ESI: 408 [MH]+

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

Reference:
Patent; Zeneca Limited; US6265411; (2001); B1;,
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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. 875003-43-3, name is 7-Fluoro-1-methylindoline-2,3-dione, A new synthetic method of this compound is introduced below., Computed Properties of C9H6FNO2

General procedure: A solution of 6-fluoro-1-methylindolin-2-one (Step B12.2) (255 mg, 1.235 mmol) in DMF (10 ml.) was cooled down to 0C and NBS (286 mg, 1.606 mmol) was added. The resulting mixture was allowed to warm up to RT then, heated up and stirred at 80C for 2 hr. The reaction mixture was diluted with EtOAc and washed with aqueous NaHC03 solution, 0.1 M LiBr and brine. The organic layer was dried over MgS04, filtered and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel (cyclohexane / 20 to 100% EtOAc) to afford the title product (222 mg, 0.591 mmol, 47.9% yield). Rt = 0.87 min (UPLC-MS); ESI-MS = 243.9 / 245.9 [M+1] + (UPLC-MS).

The synthetic route of 875003-43-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; ARISTA, Luca; CHAMOIN, Sylvie; D’ALESSANDRO, Pier Luca; LINDVALL, Mika; LIZOS, Dimitrios; STIEFL, Nikolaus Johannes; TEIXEIRA-FOUCHARD, Sylvie; ULLRICH, Thomas; WEILER, Sven; (151 pag.)WO2019/102256; (2019); A1;,
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