Author: Jessica.F

Reference of 2058-72-2,Some common heterocyclic compound, 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, molecular formula is C9H6BrNO2, 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 isatin (1) (2.0 mmol), L-proline (2) (2.0 mmol) and acrylonitrile/methyl acrylate (3/5) (2.0 mmol) in 10 mL of water was heated in an oil bath at 80 C for 3 to 6 hours. Initially reaction mixture appeared to be homogeneous but with the progress of reaction the solid precipitated out. TLC indicated the consumption of L-proline and acrylonitrile while isatin was remaining in small portion. The reaction mixture was extracted many times with ethylacetate (EA). The combine organic layer was dried over anhydrous Na2SO4 and evaporated on rotary evaporator to provide yellow colour solid. The solid was purified by silica gel column chromatography using EA:hexane (4:6) as an eluent to provide desired product 4 and 6 as white solid. The yield mentioned in the analytical data has been calculated after recovering the unreacted isatin (amount mentioned in characterization data).

The synthetic route of 2058-72-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tiwari, Keshri Nath; Pandurang, Taur Prakash; Pant, Suyash; Kumar, Rahul; Tetrahedron Letters; vol. 57; 21; (2016); p. 2286 – 2289;,
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Electric Literature of 6341-92-0, 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. 6341-92-0, name is 6-Chloroisatin belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

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 6-Chloroisatin 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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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. Product Details of 20780-72-7

General procedure: A solution of 2-nitrobenzamides 1 or bis(2-nitrobenzamides) 4 (1 mmol), isatins 2 or acenaphthylene-1,2-diones 6 (1 mmol), and SnCl2*2H2O (4 mmol) in EtOH (5 mL) was stirred at reflux for 3-5 h. After this period, the TLC analysis of the mixture showed the reaction to be completed. The mixture was quenched with 3percent HCl (10 mL) and filtered to yield a crude product, which was purified by recrystallization from 95percent ethanol and DMF.

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

Reference:
Article; Hu, Yu; Wang, Man-Man; Chen, Hui; Shi, Da-Qing; Tetrahedron; vol. 67; 48; (2011); p. 9342 – 9346;,
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Reference of 5332-26-3, 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.

General procedure: To a mixture of substituted benzyl bromide 3a-3o (1.0 mmol), sodium azide (3.0 mmol), alkyne 2 (1.0 mmol) in DMF/water (8:2), copper sulfate pentahydrate (10 mol%) and sodium ascorbate (20 mol%) were added. The reaction mixture was stirred for 4-16 h at room temperature, and the progress of the reaction was monitored by TLC. After completion of the reaction, ice-cold water (30 mL) was added to the reaction mixture. The residue thus obtained was filtered, washed with aqueous ammonium chloride/ammonia (9:1) solution and water and recrystallized with chloroform/hexane (8:2) to get 1,4-disubstituted 1,2,3-triazoles (4a-4o).

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; Lal, Kashmiri; Yadav, Pinki; Kumar, Ashwani; Medicinal Chemistry Research; vol. 25; 4; (2016); p. 644 – 652;,
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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. 64483-69-8, name is 5-Acetylindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 64483-69-8

General procedure: A 50 mL round-bottom flask equipped with a reflux condenser and a magnetic stir bar was charged with indolin-2-one (10.0 mmol), ethanol(10 mL), acetone (7.3 mL, 0.1 mmol, 10.0 equiv), benzylamine(0.33 mL, 3.0 mmol, 0.3 equiv), and acetic acid (0.17 mL, 3.0 mmol,0.3 equiv). Then, the reaction mixture was heated under reflux for 2 h. The precipitation was filtered off and washed with cold PE (10 mL). The obtained product was dried for 30 min and used without further purification.

According to the analysis of related databases, 64483-69-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Hu, Wei-Qiang; Xu, Xiu-Hua; Qing, Feng-Ling; Journal of Fluorine Chemistry; vol. 208; (2018); p. 73 – 79;,
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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. 18711-13-2, name is 4,7-Dichloroindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 4,7-Dichloroindoline-2,3-dione

General procedure: alpha-Isothiocyanato imide 2c (10.7 mg, 0.050 mmol) and catalyst 6d (2.8 mg, 0.005 mmol, 10 mol %) were dissolved in diethyl ether (1.0 mL) in a glass vial while stirring. Isatin 1a (8.8 mg, 0.060 mmol) was added and the mixture was further stirred at room temperature for 2 h. The reaction progress was monitored by TLC analysis. Upon completion, the solvent was removed under reduced pressure and the crude product was purified by flash column chromatography on silica gel (1:1 hexane/ethyl acetate) to give the desired product.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 18711-13-2.

Reference:
Article; Guang, Jie; Zhao, Cong-Gui; Tetrahedron Asymmetry; vol. 22; 11; (2011); p. 1205 – 1211;,
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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. 17564-64-6, name is 2-(Chloromethyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., category: indolines-derivatives

To a stirred suspension of sodium hydride (60% dispersion in mineral oil, 0.997 g, 24.9 mmol) in diethyl ether (100 mL) was added dimethyl 2- isobutylmalonate (3.13 g, 16.6 mmol) dropwise. The resulting mixture was stirred at RT for 3 h. The reaction mixture was cooled to 0 C. N-chloromethyl phthalimide (3.24 g, 16.6 mmol) was added in one portion. The reaction mixture was stirred at RT overnight followed by heating to reflux for 1 h. The reaction mixture was cooled to RT and cold 1.5 N HC1 (100 mL) was added. The organic layer was separated. The aqueous layer was extracted with diethyl ether (2 x 50 mL). The combined ether layers were dried over Na2S04, filtered and concentrated under reduced pressure to afford the title compound (5.3 g, 15.2 mmol, 92 % yield). The crude product was taken to next step without further purification. LCMS (ESI) m/e 347.9 [(M+H)+, calcd for Ci8H22N06, 348.1]; LC/MS retention time (method C): tR = 1.95 min.

The synthetic route of 17564-64-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; DZIERBA, Carolyn Diane; BRONSON, Joanne J.; MACOR, John E.; DASGUPTA, Bireshwar; NARA, Susheel Jethanand; VRUDHULA, Vivekananda M.; PAN, Senliang; HARTZ, Richard A.; RAJAMANI, Ramkumar; (199 pag.)WO2016/22312; (2016); A1;,
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Reference of 118-29-6,Some common heterocyclic compound, 118-29-6, name is 2-(Hydroxymethyl)isoindoline-1,3-dione, 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.

Powdered N-hydroxymethylphthalimide (70 g, 0.4 mol) was added in small portion over a period of 45 min. to a stirred solution of 2,3,3-trimethyl-(3H)-indolenine (I), (70 g, 0.44 mol) in concentrated sulfuric acid (360 mL) at room temperature. The solution was stirred for 70 h at room temperature before being poured onto ice-water. Basification of the solution with conc. ammonium hydroxide gave a yellow powder which was filtered and dried. (111 g, yield 80%, m.p. 180-182 C.). 1 H NMR (DMSO d6), delta, 7.8-7.95 (m, 4H, phthalimido), 7.4 (s, 1 H, 4-H), 7.38 (d, 1 H, J=9.0 Hz, 6-H), 7.2 (d, 1 H, J=9 Hz, 7-H), 4.7 (s, 2 H, –CH2), 2.2 (s, 3 H, CH3), 1.2 (s, 6 H –(CH3)2).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(Hydroxymethyl)isoindoline-1,3-dione, its application will become more common.

Reference:
Patent; Carnegie Mellon University; US6008373; (1999); 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 954-81-4 as follows. Formula: C13H14BrNO2

Potassium carbonate (0.50 g, 3.6 mmol) was added to a solutionof N-[(4-triphenylmethylamino)butyl]-4-nitrobenzenesulfonamide(0.93 g, 1.8 mmol) and N-(5-bromopentyl)phthalimide(0.54 g, 1.8 mmol) in DMF (12 mL). The mixture was stirred at95 C and monitored by TLC (5% EtOAc in DCM). The reactionwas diluted with ethyl acetate (100 mL) and extracted with water(4 100 mL) and brine (100 mL). The organics were dried oversodium sulfate and concentrated under reduced pressure. The residuewas purified on silica gel (1:3:96 triethylamine/ethyl acetate/dichloromethane) to yield the product as an off-white foam (1.03 g,1.41 mmol, 78%). 1H NMR (500 MHz, DMSO) d 8.35 (d, 2H, J = 9 Hz),8.02 (d, 2H, J = 9 Hz), 7.82 (m, 4H),7.35 (d, 6H, J = 8 Hz), 7.24 (t, 6H,J = 7.5 Hz), 7.13 (t, 3H, J = 7.5 Hz), 3.51 (t, 2H, J = 7 Hz), 3.07 (m, 4H),1.91 (m, 2H), 1.58 (m, 2H), 1.49 (m, 4H), 1.35 (m, 2H), 1.20 (m, 2H);13C NMR (125 MHz, CDCl3) d 168.37, 149.78, 146.04, 145.92,133.95, 132.01, 128.54, 128.16, 127.77, 126.22, 124.32,123.20,70.79, 48.22, 47.98, 42.99, 37.47, 28.08, 27.99, 27.82,26.44, 23.78; HRMS (C42H42N4O6S): calculated 730.2825, observed730.2837

According to the analysis of related databases, 954-81-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Thomson, Andrew; O’Connor, Sean; Knuckley, Bryan; Causey, Corey P.; Bioorganic and Medicinal Chemistry; vol. 22; 17; (2014); p. 4602 – 4608;,
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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. 959235-95-1, name is 6-(Trifluoromethoxy)indoline, This compound has unique chemical properties. The synthetic route is as follows., category: indolines-derivatives

A mixture of 6-(trifluoromethoxy)indoline [CAS 959235-95-1] (2 g, 9.84 mmol), 2-(4-chlorophenyl)acetic acid [CAS 1878-66-6] (1 .85 g, 10.8 mmol), HATU (5.6 g, 14.8 mmol) and diisopropylethylamine (4.9 ml_, 29.5 mmol) in DMF (40 ml_) was stirred at room temperature for 12 h. Water was added and the precipitate was filtered off. The residue was taken up with EtOAc. The organic solution was washed with a 10% aqueous solution of K2CO3, brine, dried over MgSO4, filtered and the solvent was evaporated under reduced pressure. The residue was purified by chromatography on silica gel (15-40 muiotatauiota, 80 g, heptane/EtOAc gradient 90/10 to 60/40). The pure fractions were combined and the solvent was concentrated under reduced pressure to give 2-(4-chlorophenyl)-1 -(6-(trifluoromethoxy)indolin-1 -yl)- ethanone 4a (3 g).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 959235-95-1.

Reference:
Patent; JANSSEN PHARMACEUTICALS, INC.; KATHOLIEKE UNIVERSITEIT LEUVEN; KESTELEYN, Bart Rudolf Romanie; RABOISSON, Pierre Jean-Marie Bernard; BONFANTI, Jean-Francois; BARDIOT, Dorothee Alice Marie-Eve; MARCHAND, Arnaud Didier M; (74 pag.)WO2017/167951; (2017); A1;,
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