Indolines-derivatives

These common heterocyclic compound, 1029691-06-2, name is 2-(3-Oxocyclopentyl)isoindoline-1,3-dione, 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. SDS of cas: 1029691-06-2

[0604] To a mixture of DIPEA (5.32 g, 41.17 mmol) and 151 (5.9 g, 25.73 mmol) in DCM (100 mL) was dropwise added Tf2O (8.7 g, 30.9 mmol) at 0 oC for 30 min. The reaction was stirred at 0 oC for 16 hrs. After diluted with DCM, the mixture was washed with aq. NH4Cl solution and aq. NaHCO3 solution successively. The organic phase was dried over anhydrous Na2SO4, filtered and concentrated to give crude product, which was purified by column chromatography on silica gel (eluted with petroleum ether: ethyl acetate =4: 1) to give the title compound (6.3 g, 67.7% yield) as off-white solid.

The synthetic route of 2-(3-Oxocyclopentyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WANG, Qiuping; GADHACHANDA, Venkat, Rao; WANG, Xiangzhu; DESHPANDE, Milind; PAIS, Godwin; CHEN, Dawei; WILES, Jason, Allan; HASHIMOTO, Akihiro; PHADKE, Avinash, S.; AGARWAL, Atul; (296 pag.)WO2017/35357; (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. 222036-66-0, name is 5-Aminoisoindolin-1-one, A new synthetic method of this compound is introduced below., Product Details of 222036-66-0

A mixture of 5-aminoisoindolin-1-one (50mg, 0.34mmol), the compound id (172mg, 0.5 lmmol), p-toluenesulfonic acid (96mg, 0.5 lmmol), and n-BuOH (5mL) was stirred at 70°C for3 hours. The mixture was cooled and concentrated under reduced pressure; the residue was20 purified by Pre-TLC to afford the compound 8 as yellow solid (25mg, 16percent). MS: 45 1(M+H).H-NMR (DMSO-d6, 400MHz): oe 11.18 (s, 1H), 9.98 (s, 1H), 8.92 (s, 1H), 8.40 (s, 1H), 8.02 (s, 1H), 7.57-7.79 (m, 4H), 7.30 (t, 1H), 4.30 (s, 2H), 3.00 (s, 3H), 2.90 (s, 3H).

The synthetic route of 222036-66-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JACOBIO PHARMACEUTICALS CO., LTD.; ZHOU, Wenlai; LI, Runze; GAO, Panliang; WU, Xinping; BAI, Jinlong; YANG, Guiqun; WANG, Yanping; KANG, Di; (84 pag.)WO2018/19252; (2018); A1;,
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These common heterocyclic compound, 61-70-1, name is 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. Formula: C9H9NO

General procedure: An oven-dried reflux tube equipped with a magnetic stir bar and a Teflon stopcock was charged with aryl halide (1 mmol), oxindole (1 mmol),potassium carbonate (1.1 mmol), catalyst nanoparticles (0.05 mmol)and 1,4-dioxane (2 ml) and heated at 70 C. The mixture was vigorously stirred under these reaction conditions and completion of the reaction was monitored by TLC (EtOAc: n-hexane, 25:75). After completion of the reaction, the reaction mixture was cooled to room temperature, the magnetic nanoparticles of the catalyst were collected using a magnet. Ethyl acetate (5 mL) and water (10 mL)were added to the mixture in the next step. The aqueous layer was furtherextracted by ethyl acetate (2*5 mL). The combined organic layerswere washed with saturated brine, dried over CaCl2, filtered, and concentrated to give a residue which was purified by recrystallization from ethanol and water or by column chromatography on silica gelusing EtOAc: n-hexane, 1:7.

The synthetic route of 1-Methylindolin-2-one has been constantly updated, and we look forward to future research findings.

Reference:
Article; Moghaddam, Firouz Matloubi; Tavakoli, Ghazal; Latifi, Fatemeh; Saeednia, Borna; Catalysis Communications; vol. 75; (2016); p. 37 – 41;,
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Synthetic Route of 17564-64-6, 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. 17564-64-6, name is 2-(Chloromethyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

NONOate salt N001 (0.270 g, 1.58 mmol) suspended in acetonitrile (3.0 mL) was treated with a solution of N-(chloromethyl)phthalimide (0.280 g, 1.43 mmol) in acetonitrile (3.0 mL) and then sodium iodide (0.215 g, 1.43 mmol) was added. The resulting mixture was stirred at 25 C overnight. N,N-dimethylformamide (1.0 mL) was added to the reaction mixture which was then heated to 60 C for 1 hour. The acetonitrile was removed under reduced pressure. The residue was suspended in ethyl acetate and then washed with a 0.2 N solution of sodium thiosulfate. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated. The residue was subjected to prep-chromatography using ethyl acetate in hexane to provide a tan oily solid (14 mg, 3.0% yield). 1H NMR (400 MHz, CDC13) delta 7.92-7.87 (m, 2H), 7.78-7.73 (m, 2H), 5.67 (s, 2H), 2.97 (s, 1H), 2.19 (s, 2H), 1.59 (s, 6H). LC tr=2.65 minutes (C- 18 column, 5 to 95% acetonitrile/water over 6 minutes at 1.7 mL/min with detection 254 nm, at 23 C). ES(pos)MS m/z 331 (M+Na calcd for C13Hi6N405 requires 331).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2-(Chloromethyl)isoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; EUCLISES PHARMACEUTICALS, INC.; MARTINEZ, Eduardo, J.; TALLEY, John, J.; JEROME, Kevin, D.; BOEHM, Terri, L.; WO2014/12074; (2014); A2;,
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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 39603-24-2 as follows. Formula: C10H9NO2

General procedure: A solution of isatin (1 mmol), barbituric acid (1 mmol), 3-amino-5-methyl isoxazole (1 mmol), and p-TsOH (0.2 mmol) in water (10 mL) was stirred for 24 h at 70 C in oil bath. After completion of the reaction, which was followed by TLC (n-hexane/EtOAc), the warm reaction mixture was filtered. The residue was washed with water and then recrystallized from ethanol to give the pure product.

According to the analysis of related databases, 39603-24-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Rahmati, Abbas; Khalesi, Zahra; Tetrahedron; vol. 68; 40; (2012); p. 8472 – 8479;,
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Reference of 6941-75-9,Some common heterocyclic compound, 6941-75-9, name is 5-Bromoisoindoline-1,3-dione, molecular formula is C8H4BrNO2, 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.

Example 46 (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)- phenyl)-2-(2-(5-(methylsulfonamidomethyl)-1 ,3-dioxoisoindolin-2- yl)acetoxy)ethyl)pyridine 1 -oxide (Compound 254): Scheme 46 Step 1 : Preparation of 1 ,3-dioxoisoindoline-5-carbonitrile (249): A mixture of 5-bromoisoindoline-1 ,3-dione (2.5 g, 1 1 .06 mmol) and Pd(Ph3P)4 (1 .406 g, 1 .217 mmol) in DMF (50 ml) was accurately degassed with nitrogen, then Zn(CN)2 (1 .299 g, 1 1 .06 mmol) was added and the solution, splitted in 5 vials, was heated under microwave irradiation at 200C for 1 hour. A 3% aqueous solution of NH4OH (200 ml) was added and the organic phase was extracted with ethyl acetate (3×150 ml). The combined organic layers were washed with brine (150 ml), dried over sodium sulfate and concentrated to dryness. The crude was purified by silica gel flash chromatography (100% DCM to DCM: MeOH = 99: 1 ) to afford 1 ,3-dioxoisoindoline-5-carbonitrile as (0.522 g, 3.03 mmol, 27.4% yield, MS/ESI+ 172.9 [MH] +).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromoisoindoline-1,3-dione, its application will become more common.

Reference:
Patent; CHIESI FARMACEUTICI S.P.A.; ARMANI, Elisabetta; AMARI, Gabriele; CAPALDI, Carmelida; CARZANIGA, Laura; LA PORTA, Elena; GUALA, Matilde; WO2013/57013; (2013); A2;,
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Application of 5181-35-1,Some common heterocyclic compound, 5181-35-1, name is 2-(2-Bromoethoxy)isoindoline-1,3-dione, molecular formula is C10H8BrNO3, 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 mixture of 2-(2-bromoetho xy)isoindo line- 1,3- dione (20 g, 74 mmol, prepared according to the procedure described in step 1 of preparation 10) and 2H-tetrazole-5-carboxylic acid ethyl ester (10.51 g, 74 mmol) in dimethylformamide (100 ml) was added cesium carbonate (24.13 g, 74 mmol) lot wise under stirring at room temperature. After 16 hours, the reaction mixture was filtered through filter paper and filtrate was slowly poured into chilled water (700 ml) under stirring. After 30 minutes of stirring, the product was extracted with ethyl acetate (200 ml and 100 ml). The combined organic layers were washed with brine (100 ml). The organic extract was dried over anhydrous sodium sulfate and concentrated in vacuo to yield 12.5 g of the titled compound. The compound was purified by column chromatography using mixture of acetone and hexane as an eluent. The fractions containing the compound were collected and concentrated to provide 10 g of mixture of ethyl l-{2-[(l,3-dioxo- l,3-dihydro-2H-isoindol-2- yl)oxy]ethyl}- lH-tetrazole-5-carboxylate and ethyl 2-{2-[(l,3-dioxo- l,3-dihydro-2H-isoindol-2- yl)oxy]ethyl}-2H-tetrazole-5-carboxylate in 53% yield Analysis: Mass: 332(M+1); for Molecular weight: 331 and for Molecular formula: C14H13N5O5 ; To a solution of ethyl l-{2-[(l,3-dioxo- l,3-dihydro-2H-isoindol-2-yl)oxy]ethyl}- lH-tetrazole-5-carboxylate and ethyl 2-{2-[(l,3-dioxo- l,3-dihydro-2H-isoindol-2-yl)oxy]ethyl}-2H-tetrazole-5-carboxylate (10 g, 3.02 mmol, product from step 1) in dichloromethane (100 ml) was added hydrazine hydrate (2.26 ml, 4.53 mmol) at 25- 30 C under stirring. The stirring was continued for 2 hours and the progress of reaction was monitored by thin layer chromatography using mixture of chloroform and methanol (9: 1) as solvent. After complete conversion of starting material, the unwanted solid was filtered out and washed with dichloromethane (20 ml). The filtrate was concentrated at 40 C under high vacuum to obtain 6.0 g of mixture of ethyl l-[2-(aminooxy)ethyl]- lH-tetrazole-5-carboxylate and ethyl 2- [2-(aminooxy)ethyl]-2H-tetrazole-5-carboxylate (about 100% yield), the resulted compound was used in the next step without further purification.

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

Reference:
Patent; WOCKHARDT LIMITED; TADIPARTHI, Ravikumar; PATIL, Vijaykumar Jagdishwar; DEKHANE, Deepak; SHAIKH, Mohammad Usman; BIRAJDAR, Satish; DOND, Bharat; PATEL, Mahesh Vithalbhai; (100 pag.)WO2017/81615; (2017); 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 6341-92-0 as follows. SDS of cas: 6341-92-0

General procedure: In a 50 mL flask, a mixture of hydrazine hydrate 1 (1 mmol), beta-keto ester 2 (acetylacetic ether or ethyl benzoylacetate) (1 mmol) was stirred at room temperature (78C) for 5 minutes. And then, 2-hydroxynaphthalene-1,4-dione 3 (1 mmol), isatins 4 (1 mmol), MgCl2 (0.1 mmol) and 5 mL ethanol were added to it. The mixture was stirred at 78C for the appropriate time. After completion of the reaction (monitored by TLC), the reaction mixture was cooled to room temperature, 5 mL water was added to it. Then the precipitated products were filtered and washed with cold ethanol (3 mL×2) to afford the pure products as solid powder in good to excellent yields without further purification.

According to the analysis of related databases, 6341-92-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Shen, Tianhua; Fu, Zhijie; Che, Fengfeng; Dang, Haibo; Lin, Yan; Song, Qingbao; Tetrahedron Letters; vol. 56; 9; (2015); p. 1072 – 1075;,
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Adding a certain compound to certain chemical reactions, such as: 496-12-8, name is Isoindoline, 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 496-12-8, Application In Synthesis of Isoindoline

Example 94 N-[5-(1,3-dihydro-isoindol-2-yl-carbonyl)-1-methyl-pyrrol-3-yl]-4′-trifluoromethyl-biphenyl-2-carboxylic acid amide Prepared analogously to Example 1d from 4-(4′-trifluoromethyl-biphenyl-2-carbonylamino)-1-methyl-pyrrole-2-carboxylic acid, 2,3-dihydro-1H-isoindole, TBTU and N-ethyldiisopropylamine in dimethylformamide. Yield: 79% of theory Rf value: 0.64 (silica gel; dichloromethane/ethanol=9:1)

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Isoindoline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Boehringer Ingelheim Pharma KG; US2003/162788; (2003); A1;,
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Some common heterocyclic compound, 480-91-1, name is Isoindolin-1-one, molecular formula is C8H7NO, 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. SDS of cas: 480-91-1

General procedure: Isoindolin-1-one (200 mg, 1.50mmol) was dissolved in super-dry DMSO (4 mL), and Cs2CO3 (1215 mg, 3.75 mmol), CuI (58 mg, 0.30mmol) and N1,N2-dimethylethane-1,2-diamine (27 mg, 33 muL, 0.30 mmol) were added to the solution.The resulting mixture was stirred at room temperature for 10 min, after which iodobenzene (2.25mmol) was added. Then the mixture was heated to 120 C. When TLC showed that isoindolin-1-onehad been fully converted, the reaction was stopped. The mixture was extracted with ethyl acetate (20mL) and H2O (10 mL). The water phase was re-extracted with ethyl acetate (20 mL). The organic layerwas combined and washed with brine (10 mL). Then the solution was dried over anhydrous MgSO4,filtered and concentrated, and the crude residue was purified by flash chromatography over silica gelusing CH2Cl2/CH3OH as the gradient elution to afford the title compounds.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 480-91-1, its application will become more common.

Reference:
Article; Wang, Yixuan; Wang, Huiqiang; Jiang, Xinbei; Jiang, Zhi; Guo, Tingting; Ji, Xingyue; Li, Yanping; Li, Yuhuan; Li, Zhuorong; Molecules; vol. 24; 5; (2019);,
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