Indolines-derivatives

Some common heterocyclic compound, 40314-06-5, name is 5-Methylisoindoline-1,3-dione, molecular formula is C9H7NO2, 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. Recommanded Product: 5-Methylisoindoline-1,3-dione

N-4-methylphenylglycine ethyl ester (0.3 mmol) under air atmosphere,A phthalimide compound (0.2 mmol) and cuprous chloride (0.02 mmol) were placed in a dry reaction tube with stirring magnets.Then into the test tubeAn acetonitrile solvent (2 mL) was added and the reaction tube was reacted in an air atmosphere at 60 C for 24 hours.After the reaction was completed, it was cooled to room temperature, and the solvent was distilled off under reduced pressure using a rotary evaporator.The residue was purified by column chromatography to give a pure pale yellow solid 3 mThe yield was 65%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 40314-06-5, its application will become more common.

Reference:
Patent; Donghua University Of Science And Technology; Zhu Zhiqiang; Xiao Lijin; Xie Zongbo; Yue Changgao; (12 pag.)CN108623514; (2018); A;,
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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. 110568-64-4, name is 6-Nitroisoindolin-1-one, A new synthetic method of this compound is introduced below., Recommanded Product: 110568-64-4

Synthesis of tert-butyl 5-nitro-1-oxoisoindoline-2-carboxylate (2) To a stirred solution of 5-nitroisoindolin-1-one (1, 0.4 g, 2.24 mmol) in acetonitrile (20 mL), N,N-dimethylaminopyridine (0.41 g, 3.37 mmol) followed by di-tert-butyl dicarbonate (0.75 mL, 3.37 mmol) were added. The reaction mixture was allowed to stir at room temperature for 12 h. The reaction mixture was quenched with water and extracted with ethyl acetate. The organic layer was washed with brine, separated, dried over sodium sulphate and concentrated under reduced pressure. The crude was purified by silica gel column chromatography using 25% ethyl acetate in hexane to afford tert-butyl 5-nitro-1-oxoisoindoline-2-carboxylate (2). Yield: 0.36 g, 57%; MS (ESI) m/z 279 [M+1]+.

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; eFFECTOR Therapeutics, Inc.; Sprengeler, Paul A.; Reich, Siegfried H.; Ernst, Justin T.; Webber, Stephen E.; Shaghafi, Mike; Murphy, Douglas; Tran, Chinh; (131 pag.)US10112955; (2018); B2;,
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Application of 20870-78-4, 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. 20870-78-4 name is 5-Bromoindolin-2-one, 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.

5-Bromo-2-oxindole 16 (150 mg, 0.71 mmol), benzeneboronic acid (113 mg, 0.92 mmol), tetrakis(triphenylphosphine)palladium(0) (61 mg, 0.05 mmol) and Natrium carbonate (250 mg, 2.41 mmol) were suspended in toluene (1.5 mL) and ethanol (1.5 mL) and refluxed for 12 h at 100 C. Water was added and extracted 3 times with ethyl acetate. The combined organic layers were wash with 1N hydrochloric acid, brine, dried over MgSO4, filtered and concentrated in vacuum to give 75 mg (51%) as a light brown solid and was used for the next step without further structure determination.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromoindolin-2-one, and friends who are interested can also refer to it.

Reference:
Article; Goering, Stefan; Taymans, Jean-Marc; Baekelandt, Veerle; Schmidt, Boris; Bioorganic and Medicinal Chemistry Letters; vol. 24; 19; (2014); p. 4630 – 4637;,
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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. 141452-01-9, name is Methyl indoline-5-carboxylate, A new synthetic method of this compound is introduced below., HPLC of Formula: C10H11NO2

The indoline-5-carboxylate (177mg, 1.0mmol) was dissolved in pyridine (4mL), and4- (4- (2- (3- (chlorosulfonyl) benzamido) -4,5,6,7-tetrahydro-benzo [b] thiophen-3-carboxamido) phenethyl) benzoate (800mg, 1.26mmol),The reaction was heated to reflux for 18 hours.The reaction solution was diluted with ethyl acetate (80mL),0.1mol / L hydrochloric acid and washed (10mL ¡Á 3).The organic phase was dried over anhydrous sodium sulfate,concentrate.The crude product was purified by silica gel column chromatography (petroleum ether / dichloromethane (v / v) = 1/1) to give a yellow solid 491mg,Yield: 63.2%.

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; Guangdong East Sunshine Pharmaceutical Co., Ltd.; Wang, Xiaojun; Yang, Xinye; Zhou, Pingjian; Yang, Chuanwen; Lin, Jihua; Xiong, Shaohui; Zhang, Yingjun; Xiao, Ying; Wang, Hui; Cao, Shengtian; Wu, Fangyuan; Ouyang, Luo; (74 pag.)CN105524053; (2016); A;,
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Synthetic Route of 19727-83-4,Some common heterocyclic compound, 19727-83-4, name is 6-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.

6-Nitroindoline (5 g) was dissolved in 200 mL ofdichloroethane. N-Methyl-4-piperidone (5 g) was added to themixture, followed by NaHB(OAc)3 (12 g) and 1 mL of glacialAcOH. The mixture was stirred at RT overnight. A saturatedNaHC03 (200 mL) solution was added to the reaction mixtureand stirred for 1 h. The resulting mixture was separated byseparation funnel. The organic layer was extracted once withsaturated NaHC03 solution and once with brine. The resultingorganic layer was dried over MgS04, filtered andconcentrated in vacuo. The crude material was purified byflash chromatography on silica gel with 2:1 EtOAc:MeOH toafford orange oil. MS: 262 (M+l) . Calc’d. for C14H19N302 -261.3.

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

Reference:
Patent; AMGEN INC.; WO2006/12374; (2006); A1;,
Indoline – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 5428-09-1, name is 2-Allylisoindoline-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 5428-09-1, SDS of cas: 5428-09-1

To a solution of 2-allylisoindoline-1,3-dione 11(13.0 g, 69.4 mmol) in CH2CI2 (500 mL) was added AIIyITMS (79.0 g, 110 mL, 694 mmol) and Grubbs I generation catalyst. The reaction was heated to 60 ¡ãC and stirred under reflux for 4 h.Tris(hydrodxymethyl)phosphine (1 M solution in i-PrOH, 58 mL) was added and stirred under reflux for 12 h, while the color of the reaction turned from black to orange. Sat. aq. NaCI solution (100 mL) was added to the reaction and the organic phase was separated. The aqueous phase was extracted with CH2CI2 (3 x 200 mL). The combined organic layers were dried over MgSO4 and the solvent was removedunder reduced pressure. Column chromatography over SiC2 (Cyclohexane/ EtOAc =85:15) afforded the title compound (15.0 g, 54.9 mmol, 78.9 percent) as a yellow resin.R: 0.57 (Cyclohexane/EtOAc = 85:15)1H NMR (300 MHz, CDCI3) 6 = -0.10?0.09 (m, 9H), 1.44 (d, J = 8.2 Hz, 1.6 H), 1.72(d, J= 8.8 Hz, 0.4 H), 4.21 (d, J= 6.5 Hz, 1.6 H), 4.29 (dd, J= 14.5, 5.9 Hz, 0.4 H),5.26 ? 5.47 (m, 0.8 H), 5.56 ? 5.70 (m, 0.2 H), 5.70 ? 5.87 (m, 0.8 H), 5.94 ? 6.09 (m,0.2 H), 7.65 ? 7.74 (m, 2H), 7.79 ? 7.88 (m, 2H).?3C NMR (75 MHz, cdcl3) 6 = -2.05, -1.83, -1.43, 18.92, 22.73, 34.72, 39.87, 120.51,121.30, 123.12, 130.78, 132.24, 133.76, 133.90, 167.99.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Allylisoindoline-1,3-dione, and friends who are interested can also refer to it.

Reference:
Patent; MAX-PLANCK-GESELLSCHAFT ZUR FOeRDERUNG DER WISSENSCHAFTEN E.V.; WANG, Yansong; HAUSCH, Felix; BISCHOFF, Matthias; POMPLUN, Sebastian; WO2015/110271; (2015); A1;,
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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. 1914-02-9, name is 3,3-Dimethylindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 3,3-Dimethylindoline

EXAMPLE 1 N-(3,3-Dimethylindolin-1-yl)-3-(4-imidazolyl)propionamide monohydrochloride (E1) STR9 A suspension of 3-(4-imidazolyl)propionic acid monohydrochloride (2.0 g) (Chem. Ber. 66, 156 [1933]) in thionyl chloride (10 ml) and DMF (3 drops) was stirred at room temperature for 3 h. The excess thionyl chloride was removed by rotary evaporation and the residue re-evaporated with 2*50 ml of dry toluene. The residue was suspended in CH2 Cl2 (100 ml) and a solution of 3,3-dimethyl indoline (1.7 g) and triethylamine (4 ml) in CH2 Cl2 (50 ml) was added with stirring and cooling. The reaction mixture was stirred overnight, washed with saturated NaHCO3 and the lower organic layer dried (Na2 SO4). Concentration of the organic extracts afforded the crude product which was purified by column chromatography on silica, eluding with CHCl3 containing increasing quantities of methanol.

The synthetic route of 1914-02-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Beecham Group p.l.c.; US4918079; (1990); 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 132898-96-5 as follows. COA of Formula: C8H4ClNO4S

General procedure: To a stirred solution of the N-Boc-protected pyrrolidine (1.0 mmol) in dry DCM (3 mL) at 0 C under argon atmosphere, TFA (1.14 g, 10.0 mmol) was added dropwise. The obtained solution was stirred at 0 C for 30 min followed by stirring at r.t. for 2 h. Subsequently, the solution was poured to cold 10% aq. NaOH (15 mL) and extracted with DCM (3 ¡Á 15 mL). The combined organic phases were dried over MgSO4 and concentrated under reduced pressure resulting in the corresponding unprotected pyrrolidine, which was used in the next step without further purification. The free pyrrolidine (ca. 1 mmol) from the previous step was then taken up in CHCl3 (2.2 mL) and DIPEA (2.0 mmol) was added. The solution was added dropwise to a stirred solution of 5-chlorosulfonyl isatin (1.5 mmol) in CHCl3/THF (1:1, 15 mL) at room temperature. The resulting mixture was stirred further for 1 h and the solvent was removed under reduced pressure. After purification by flash column chromatography the target isatin sulfonamide was obtained.

According to the analysis of related databases, 132898-96-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Limpachayaporn, Panupun; Riemann, Burkhard; Kopka, Klaus; Schober, Otmar; Schaefers, Michael; Haufe, Guenter; European Journal of Medicinal Chemistry; vol. 64; (2013); p. 562 – 578;,
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1029691-06-2, name is 2-(3-Oxocyclopentyl)isoindoline-1,3-dione, 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. Recommanded Product: 2-(3-Oxocyclopentyl)isoindoline-1,3-dione

Example 58B 2-(3-hydroxy-3-phenylcyclopentyl)isoindoline-1,3-dione A solution of Example 58A (1.00 g, 4.36 mmol) and THF (20 mL) was cooled to <-70 C. and phenylmagnesium chloride (2.40 mL, 4.80 mmol) was added at <-70 C. After 2 hours, saturated aqueous NH4Cl (20 mL) was added and the mixture was extracted with MTBE (50 mL). The organic layer was dried (Na2SO4) and concentrated. The residue was puridifed by flash column chromatography (0-20% EtOAc/hexanes, gradient elution), to provide the title compound (370 mg, 1.20 mmol, 27.6% yield). The synthetic route of 1029691-06-2 has been constantly updated, and we look forward to future research findings. Reference:
Patent; ABBOTT LABORATORIES; US2012/245163; (2012); A1;,
Indoline – Wikipedia,
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Application of 3484-35-3,Some common heterocyclic compound, 3484-35-3, name is 5-Methylindolin-2-one, molecular formula is C9H9NO, 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: To a solution of appropriate oxindole (7a-e, 0.3 mmol) in ethanol (3 mL) was added corresponding aldehydes (11a-e,0.32 mmol) and a catalytic amount of piperidine. The reaction mixture was stirred at reflux for 6-12 h (reaction monitored byTLC). After cooling, the precipitate was filtered, washed with cold ethanol, and dried in air to furnish pure (Z)-3-(3′-methoxy-4′-(2-amino-2-oxoethoxy)-benzylidene)indolin-2-ones title compounds of formula (4a-v) as yellow/brown/orange solids in moderate to excellent yields.

The synthetic route of 3484-35-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Senwar, Kishna Ram; Reddy, T. Srinivasa; Thummuri, Dinesh; Sharma, Pankaj; Naidu; Srinivasulu, Gannoju; Shankaraiah, Nagula; European Journal of Medicinal Chemistry; vol. 118; (2016); p. 34 – 46;,
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