Month: June 2021

Electric Literature of 60434-13-1, 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. 60434-13-1, name is 5-Chloro-1-methylindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of N-benzylisatin (1a, 1.0 mmol), in dryTHF, trimethyl(trifluoromethyl)silane (TMSCF3,2.0 mmol) was added dropwise at room temperature. Tothis 0.052 g TBAF (20 mol %) was added and then thereaction mixture was stirred at room temperature untilcomplete conversion takes place as indicated by TLCanalysis. The reaction mixture was treated with aqueousNaHCO3 and was extracted with ethyl acetate. The organiclayers were collected and dried with anhydrous Na2SO4,followed by solvent removal under reduced pressure. Thecrude product was purified by flash chromatography(hexane/ethyl acetate = 90:10) on silica gel to give thedesired product.

The chemical industry reduces the impact on the environment during synthesis 5-Chloro-1-methylindoline-2,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Article; Bikshapathi, Raktani; Prathima, Parvathaneni Sai; Yashwanth; Pamanji; Jagadeeshkumar; Maheshwari; Rao, J. Venkateswara; Murty; Rao, V. Jayathirtha; Monatshefte fur Chemie; vol. 148; 4; (2017); p. 757 – 764;,
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Application of 1055412-47-9, 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. 1055412-47-9, name is su-5614 belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A suspension of 5-chloro-3-(1H-pyrrol-2-yl-methylene)-1,3-dihydro-indol-2-one (120 mg, 0.44 mmol), morpholine (39 muL, 0.44 mmol) and paraformaldehyde (20 mg, 0.66 mmol) in 8 mL of dioxane and 2 mL of EtOH was heated to 80 C. for 15 h. The reaction mixture was cooled to room temperature and treated with morpholine (25 muL, 0.28 mmol) and paraformaldehyde (16 mg, 0.50 mmol) The reaction mixture was heated at 80 C. for 4 h. The reaction mixture was cooled to room temperature and partially concentrated under a nitrogen stream. The reaction mixture was cooled to -20 C. The solid which formed was collected by filtration and rinsed with EtOH (previously cooled to -20 C.). The solid collected was dried under vacuum to give the title compound (85 mg, 52%) as an orange solid.

The synthetic route of su-5614 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Allergan, Inc.; US2004/102509; (2004); A1;,
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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. 3891-07-4, name is 2-(2-Hydroxyethyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2-(2-Hydroxyethyl)isoindoline-1,3-dione

In the first step, under a nitrogen atmosphere, 3.00 mmol of thiacup [4] arene, 25.71 mmol of hydroxyethylphthalimide,9.15 mmol of triphenylphosphine, 120 mL of dry tetrahydrofuran (drying treatment before use), stir well and cool to zero in an ice-salt bath.9.14 mmol of diethyl azodicarboxylate was dissolved in 30 mL of dry tetrahydrofuran, and then placed in a constant pressure funnel and slowly dropped into a three-necked flask. After the dropwise addition was completed, the temperature was raised to room temperature for 72 hours.At the end of the reaction, the solvent was evaporated to dryness, and methanol was added while hot to precipitate a large amount of white solid. After suction filtration, the filter cake was dried.Purification by silica gel column chromatography (n-hexane: ethyl acetate = 8: 2) to obtain 2.43 g of 1,3-alternate-bis (2-phthalimide) thiacalix [4] arene, yield Is 75.8%,1,3-Alternate-bis (2-phthalimide) thiacalix [4] arene has the structural formula shown in Formula (II):

According to the analysis of related databases, 3891-07-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shenzhen Advanced Technology Institute; Zhao Jianglin; Jin Zongwen; Ruan Qin; Chen Zhenmin; Luo Qingying; Wu Yutian; (22 pag.)CN107936953; (2019); B;,
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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. 611-09-6, name is 5-Nitroindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., category: indolines-derivatives

General procedure: A mixture of isatin (1 mmol), malononitrile or cyanoacetic esters (1 mmol), 1,3-dicarbonyl compounds (1 mmol), and the catalyst (10 wt %) in ethanol (3 ml) was stirred at 80 C for a specified time (see Table 2). After complete conversion, as indicated by TLC, the reaction mixture was cooled to room temperature. The resulting solid precipitate was filtered and dried along with the catalyst. Further purification of the product was performed by recrystallization using ethanol and the catalyst was recovered by filtration.

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 611-09-6.

Reference:
Article; Maheshwar Rao; Reddy, G. Niranjan; Reddy, T. Vijaikumar; Devi, B.L.A. Prabhavathi; Prasad; Yadav; Reddy, B.V. Subba; Tetrahedron Letters; vol. 54; 20; (2013); p. 2466 – 2471;,
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Reference of 774-47-0, 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 774-47-0 as follows.

General procedure: In a 15 mL quartz tube equipped with a magnetic stirrer bar, isatin (1 mmol), 1,3-dicarbonyl compound (1 mmol), malononitrile (1 mmol), and Na2 eosin Y (0.02 mmol) were added successively in ethyl lactate/water (3:1, 2 mL). The reaction tube was exposed to green LED (520e525 nm, 10 W) irradiation at a distance of approximately 3 mm from bottom of the tube (SI, Fig. S1) at room temperature in air with stirring for an appropriate time. The reaction progress was monitored by TLC. Upon completion, water was added to the mixture and the solid precipitate was filtered and washed with ethanol to obtain the desired pure product.

According to the analysis of related databases, 774-47-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Chen, Meng-Nan; Di, Jia-Qi; Li, Jiao-Mian; Mo, Li-Ping; Zhang, Zhan-Hui; Tetrahedron; (2020);,
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Electric Literature of 7699-18-5, 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. 7699-18-5, name is 5-Methoxyindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 5-methoxy-2,3-dihydro-1H-indole-2-one (5 g, 30.64 mmol) and diisopropylamine (6.14 g, 60.79 mmol) in anhydrous tetrahydrofuran (50 mL) was slowly added n-butyllithium (49 mL, 122.68 mmol, 2.5 M n-hexane solution).The mixture was stirred for 1 hour and 1,2-dibromoethane (6.89 g, 36.68 mmol) was slowly added.The mixed solution was transferred to room temperature for reaction. The reaction was then quenched by adding 100 mL of water,And extracted with ethyl acetate (3 x 300 mL). The combined organic layers were dried over anhydrous sodium sulfate,Suction filtered and concentrated in vacuo. Passing a gradient flash column (ethyl acetate / petroleum ether) gave compound 10 as an off-white solid, 2.5 g, yield 43%.

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

Reference:
Patent; Guangdong Pharmaceutical University; Ye Lianbao; Shi Peiqi; Zhu Daqian; Zhao Tao; Chen Weiqiang; Gao Wei; Luo Yan; (27 pag.)CN110256429; (2019); A;,
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Synthetic Route of 675109-45-2,Some common heterocyclic compound, 675109-45-2, name is 6-Amino-2,3-dihydro-1H-isoindol-1-one, molecular formula is C8H8N2O, 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.

3H:; [00255] Intermediate 2 (164 mg, 1.11 mmol), 3G (535 mg, 1.00 mmol), and glyoxylic acid monohydrate (111 mg, 1.21 mmol) were taken up in CH3CN (3 mL) and DMF (2 ml). The mixture was stirred at 600C for 48 h, then was concentrated. The crude product was purified by flash chromatography (1 to 20% MeOH/CH2Cl2 gradient) to afford 313 mg of 3H as a pale yellow solid. MS (ESI) m/z 693.3 (M+H)+

The synthetic route of 675109-45-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2008/79836; (2008); A2;,
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24566-79-8, name is N-(6-Bromohexyl)phthalimide, 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: 24566-79-8

Triphenylmethanethiol (11.90 g, 43.08 mmol) was suspended in DMSO (40 mL). DBU (7.41 mL, 49.55 mmol) and 6-bromohexylphthalimide (13.32 g, 42.94 mmol) were added, and the mixture was allowed to react for approximately 15 min. The reaction mixture was partitioned between ethyl acetate (700 mL) and 0.1 M HCl (200 mL). The aqueous phase was extracted with ethyl acetate (3×50 mL), and the combined organic fractions were washed with NaHCO3 sat. (80 mL) and brine (80 mL), dried over MgSO4, filtered and concentrated. The crude yellow oil was recrystallized from n-heptane/ethyl acetate. The intermediate 6-(S-Trityl-)mercaptohexylphthalimide was obtained as a white solid (13.3 g, 26.4 mmol, 62%).

The synthetic route of 24566-79-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANOFI-AVENTIS DEUTSCHLAND GMBH; Sprogoe, Kennett; Cleemann, Felix; Hersel, Ulrich; Kaden-Vagt, Silvia; Lessmann, Torben; Rau, Harald; Wegge, Thomas; (61 pag.)US9265723; (2016); B2;,
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Electric Literature of 334952-09-9, These common heterocyclic compound, 334952-09-9, name is 2-Oxoindoline-6-carboxylic acid, 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.

Example 8 N-(1-(7-(3,4-Dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)pyrrolidin-3-yl)-2-oxoindoline-6-carboxamide Procedure: A mixture of 5-(3-aminopyrrolidin-1-yl)-N-(3,4-dimethoxyphenyl)thiazolo[5,4-d]pyrimidin-7-amine hydrochloride (82 mg, 0.2 mmol), 2-oxoindoline-6-carboxylic acid (36 mg, 0.2 mmol), EDCI (76 mg, 0.4 mmol) and N-methylimidazole (50 mg, 0.6 mmol) in 5 mL of DCM was stirred at room temperature for 16 hours. The mixture was washed with water (4 mL), The organic layer was dried over Na2SO4. After filtration and concentration, the residue was purified by preparative TLC (Silica gel, 20 cm*20 cm, separated by EtOAc, eluted by DCM_MeOH=1:20, v/v) to give N-(1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)pyrrolidin-3-yl)-2-oxoindoline-6-carboxamide (25 mg, 23.5%). 1H NMR (300 MHz, DMSO): delta 10.52 (s, 1H), 9.56 (s, 1H), 8.81 (s, 1H), 8.61 (d, 1H, J=6.3 Hz), 7.90 (brs, 1H), 7.48-7.46 (m, 2H), 7.28-7.25 (m, 2H), 6.93-6.90 (m, 1H), 4.54 (brs, 1H), 3.77-3.34 (m, 11H), 2.50-2.34 (m, 1H), 2.07-1.99 (m, 2H). LC-MS: 532 [M+H]+, 530 [M-H]-, tR=1.35 min. HPLC: 97.39% at 214 nm, 97.05% at 254 nm, tR=4.54 min.

Statistics shows that 2-Oxoindoline-6-carboxylic acid is playing an increasingly important role. we look forward to future research findings about 334952-09-9.

Reference:
Patent; Hermann, Johannes Cornelius; Lowrie, JR., Lee Edwin; Lucas, Matthew C.; Luk, Kin-Chun Thomas; Padilla, Fernando; Wanner, Jutta; Xie, Wenwei; Zhang, Xiaohu; US2012/252777; (2012); 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 61-70-1 as follows. Application In Synthesis of 1-Methylindolin-2-one

To 10 ml schlenk bottle adding N – methyl -2 – indolone (1 a, 0.3 mmol), tert-butyl nitrite (t – BuONO, 2 a, 0.6 mmol) and THF (2 ml), then oxygen atmosphere (1 atm) next, the reactor is placed 25 C stirring under the conditions of reaction, monitoring the reaction by TLC or GC process, to the reaction raw material N – methyl -2 – indolone reaction is complete, to stop the reaction, the reaction the fluid uses full and salt water washing, recovering the organic phase, the aqueous phase is extracted with ethyl acetate, the combined organic phase; organic phase was dried with anhydrous sodium sulfate, filtered, distilled under reduced pressure, the residue by column chromatography (petroleum ether/ethyl acetate) separation to obtain the target product N – methyl isatin, I – 2, the isolation yield is 73%,1

According to the analysis of related databases, 61-70-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ningbo University; Huang Yiling; Wei Wenting; Ying Weiwei; Wu Yi; Wu Kewei; Cao Yiqi; Wang Yining; Zhu Liwei; (8 pag.)CN107141246; (2017); A;,
Indoline – Wikipedia,
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