Month: August 2021

Reference of 3485-84-5, A common heterocyclic compound, 3485-84-5, name is N-Vinylphthalimide, molecular formula is C10H7NO2, 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.

A 20-mL, microwave reaction vessel was charged with (4-bromopyridin-3-yl)-(4-(trifluoro methyl)phenyl)methanol (0.87 g, 2.62 mmol), 2-vinylisoindoline-1,3-dione (499 mg, 2.88 mmol), Pd(dba)2 (75.3 g, 0.13 mmol), 2-(dicyclohexyl-phosphino)biphenyl (91.8 mg, 0.26 mmol), NEt3 (0.44 ml, 3.14 mmol), and DMF (2 mL). The mixture was purged with argon and heated in microwave synthesizer at 150 C. for 1 h. The reaction mixture was partitioned between water and EtOAc. The EtOAc layer was separated and aqueous layer was extracted again with EtOAc. The combined organic layers were washed with saturated NaHCO3, dried over Na2SO4, filtered, and concentrated in vacuo. The resulting residue was purified by silica gel chromatography (0-10% MeOH in DCM) to give the mixture (0.4 g) of (E)-2-(2-(3-(hydroxy(4-(trifluoromethyl)phenyl)methyl)pyridin-4-yl)-vinyl) isoindoline-1,3-dione and 2-(2-(3-(hydroxy(4-(trifluoromethyl)phenyl)-methyl)pyridin-4-yl)ethyl)isoindoline-1,3-dione as a light yellow semi-solid. MS (ESI pos. ion) m/z: 425 and 427.

The synthetic route of 3485-84-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nishimura, Nobuko; Norman, Mark H.; Tamayo, Nuria; Tang, Phi; Bo, Yunxin Y.; US2009/82358; (2009); A1;,
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Related Products of 20870-79-5, 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. 20870-79-5, name is 5-Nitroindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Appel?s salt (Scheme 2, 1; 4,5-dichloro-1,2,3-dithiazolium chloride; 15.76 mmol) was added to asolution of each appropriate 2-oxindole derivative (Scheme 2, 2a-d; 14.33 mmol) in CH2Cl2 (20 mL).After a few minutes, the uncolored mixture turned to a dark red color, and was stirred at roomtemperature for 18 h. The solvent was evaporated under reduced pressure, and the crude productwas dissolved with acetone (a minimum of 30 mL), and then precipitated with water (300 mL).The heterogeneous mixture was filtered in a vacuum, and the red solid was washed three times withwater (25 mL). This solid was finally dried over phosphorus pentoxide in a vacuum in a desiccator.

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

Reference:
Article; Letribot, Boris; Delatouche, Regis; Rouillard, Herve; Bonnet, Antoine; Cherouvrier, Jean-Rene; Domon, Lisianne; Besson, Thierry; Thiery, Valerie; Molecules; vol. 23; 6; (2018);,
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These common heterocyclic compound, 18711-13-2, name is 4,7-Dichloroindoline-2,3-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. HPLC of Formula: C8H3Cl2NO2

General procedure: A mixture of 1 (0.4 mmol), 2 (0.4 mmol), Na2CO3 (0.8 mmol) and TBHP (0.4 mmol) in DMF (4 mL) was stirred at rt for 2 h. Then, the mixture was poured into ice-water, acidified with 1 N HCl aq. (6 mL). The mixture was extracted with ethyl acetate (20 mL x 3). The combined organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by silica gel flash column chromatography to give desired products..

The synthetic route of 4,7-Dichloroindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wu, Jun; Zhang, Hui; Ding, Xiao; Tan, Xuefei; Shen, Hong C.; Chen, Jie; He, Weimin; Deng, Hongmei; Song, Liping; Cao, Weiguo; Journal of Fluorine Chemistry; vol. 220; (2019); p. 54 – 60;,
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Electric Literature of 20876-36-2, 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. 20876-36-2, name is 5-Aminoindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 1 A mixture of 5-aminooxindol (14 g), 29 g of bis(beta-bromoethyl)amine.hydrobromide in 250 ml of ethanol was stirred under reflux for 8 hours and allowed to stand overnight at room temperature. To the mixture was added sodium carbonate (10.1 g) and the mixture was stirred further for 8 hours under reflux. After cooling to room temperature, crystals which precipitated were collected by filtration and recrystallized from a mixture of water and ethanol to give 16 g of 5-(1-piperazinyl)oxindol.hydrobromide. Pale yellow powdery crystal NMR (200 MHz, DMSO-d6) delta: 3.30 (8H, s), 3.47 (2H, s), 6.78 (1H, d, J=8.5 Hz), 6.90 (1H, dd, J=8.5 Hz, 2 Hz), 7.04 (1H, d, J=2 Hz), 8.88 (2H, brs), 10.27 (1H, s)

The synthetic route of 5-Aminoindolin-2-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Otsuka Pharmaceutical Co., Ltd.; US4737501; (1988); A;,
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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. 5181-35-1, name is 2-(2-Bromoethoxy)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 5181-35-1

To a solution of 2-(2-bromoethoxy)isoindoline- l,3-dione (20 g, 7 mmol, step 1 product) in dimethylformamide (100 ml) was added 1H- 1,2,4 triazole (5.2 g, 7.52 mmol) and cesium carbonate (26.5 g, 8.13 mmol) under stirring at 25-30 C. After 16 hours of stirring, the reaction mixture was filtered through filter paper and the filtrate was slowly poured into chilled water (700 ml) under stirring. After 30 minutes, the separated precipitates were filtered and washed with water (50 ml). The filtered precipitates were dried at 40C for 2 hour under high vacuum to provide 10.5 g of 2-[2- (lH- l,2,4-triazol- l-yl)ethoxy]- lH-isoindole- l,3(2H)-dione as white solid in 55% yield. Analysis: Mass: 259.2 (M+l) for Molecular weight: 258 and for Molecular formula: C12H10N4O3

According to the analysis of related databases, 5181-35-1, the application of this compound in the production field has become more and more popular.

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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Indoline | C8H9N – PubChem

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. 954255-04-0, name is 5,6-Difluoroindoline, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H7F2N

Example 46 5-(6-(5,6-difluoroindoline-1-carbonyl)pyrimidin-4-ylamino)-1,3-dihydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-2′(1’H)-one 0.10 g (0.24 mmol) 6-(2′-oxo-1,1′,2′,3-tetrahydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-5-ylamino)pyrimidine-4-carboxylic acid hydrochloride, 50 mg (0.26 mmol) 5,6-difluoro-2,3-di-hydro-1H-indole, 0.10 mL (0.72 mmol) TEA and 80 mg (0.25 mmol) TBTU in 1.8 mL DMF were stirred overnight at RT. The purification was carried out by preparative HPLC-MS. The product-containing fractions were combined and lyophilised. Yield: 45 mg (36% of theory) ESI-MS: m/z=511 (M+H)+ Rt (HPLC-MS): 1.61 min (method C)

According to the analysis of related databases, 954255-04-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/21500; (2011); A1;,
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Reference of 20870-78-4, A common heterocyclic compound, 20870-78-4, name is 5-Bromoindolin-2-one, molecular formula is C8H6BrNO, 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.

To a solution of 5-bromo-2-oxindole (21 g, 100 mmol) in 1 ,4-dioxane (150 mL) was added bis(pinacolato)diboron (38 g, 150 mmol), l , l-bis(diphenylphosphino) ferrocene-palladium(II) dichloride dichloromethane complex (8.2 g, 10 mmol), and potassium acetate (20 g, 200 mmol). The resulting mixture was degassed and then stirred overnight at 80 C under an Ar atmosphere. After the reaction was completed as monitored by LC-MS, the mixture was diluted with water (500 mL) and then extracted with EtOAc. The combined organic layers were washed with water and brine, and then dried. The solvent was concentrated and the residue was purified by column chromatography (EtOAc / Pet = 2: 1) to give oxindole-5-boronic acid pinacol ester (15 g) as a white solid.

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

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; HAN, Xingchun; JIANG, Min; WANG, Jianhua; WANG, Min; YANG, Song; ZHOU, Chengang; WO2014/90692; (2014); A1;,
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Related Products of 2058-72-2, 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 2058-72-2 as follows.

General procedure: A solution of isatins 1 (0.6 mmol), 3-methyl-4-nitro-5-isatylidenylisoxazoles 2 (0.4 mmol) and proline or thioproline (0.8 mmol) in the 10.0 mL of EtOH at reflux for 5 h. After completion of the reaction, as indicated by TLC, the reaction mixture was directly subjected to flash column chromatography on silica gel (petroleum ether/EtOAc = 5:1-3:1) to furnish the corresponding products 3.

According to the analysis of related databases, 2058-72-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Lin, Bing; Zhang, Wen-Hui; Wang, Dan-Dan; Gong, Yi; Wei, Qi-Di; Liu, Xiong-Li; Feng, Ting-Ting; Zhou, Ying; Yuan, Wei-Cheng; Tetrahedron; vol. 73; 34; (2017); p. 5176 – 5188;,
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Reference of 102359-00-2, A common heterocyclic compound, 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, molecular formula is C9H7NO3, 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.

1-[2-Oxo-5-(pyrrolidine-1-carbonyl)-1,2-dihydro-indol-3-ylidenemethyl]-2,5,6,7-tetrahydro-pyrrolo[3,4-c]pyridin-4-one PyBOP (3.5 g, 6.72 mmol) was added to a mixture of 5-carboxy-2-oxindole (1 g, 5.6 mmol), pyrrolidine (0.5 mL, 6.2 mmol) and triethylamine (2.0 mL, 14 mmol) in dichloromethane. After stirring at room temperature for 4 hours, the reaction was diluted with more dichloromethane, washed with saturated sodium bicarbonate and brine, dried and concentrated. The residue was purified by column chromatography to give 5-(pyrrolidine-1-carbonyl)-1,3-dihydro-indol-2-one. 1H NMR (300 MHz, DMSO-d6) delta 10.52 (br s, 1H, NH), 7.37 (m, 2H), 6.80 (d, J=8.5 Hz, 1H), 3.49 (s, 2H, CH2), 3.42 (m, 4H, 2xCH2), 1.81 (m, 4H, 2*CH2). MS-El m/z 230 [M+].

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; Tang, Peng Cho; Miller, Todd A.; Li, Xiaoyuan; Zhang, Ruofei; Cui, Jinrong; Huang, Ping; Wei, Chung Chun; US2002/42427; (2002); A1;,
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Synthetic Route of 2436-29-5,Some common heterocyclic compound, 2436-29-5, name is 3-(1,3-Dioxoisoindolin-2-yl)propanal, molecular formula is C11H9NO3, 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.

3-(1,3-Dioxoisoindolin-2-yl)propanal (2.5 g, 12.3 mmol) was dissolved in 80 mL of DCM. (1ethoxycarbonylethylidene)triphenylphosphorane (4.50 g, 12.9 mmol) was added thereto, and the mixtue was stirred at room temperaturefor 2 hours. The reaction solution was concentrated under reduced pressure and purified by column chromatography toobtain the title compound (2.99 g, 89 %).1H-NMR (CDCl3) delta7.83 (2H, m), 7.72 (2H, m), 6.91 (1H, m), 5.90 (1H, d), 4.16 (2H, q), 3.83 (2H, t), 2.60 (2H, m), 1.26 (3H, t)

The synthetic route of 2436-29-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LG Chem, Ltd.; KIM, Young Kwan; PARK, Sang Yun; JOO, Hyun Woo; CHOI, Eun Sil; PAEK, Seung Yup; KANG, Seung Wan; KIM, Byung Gyu; LEE, Chang Seok; KIM, Sung Wook; LEE, Sang Dae; (369 pag.)EP3239143; (2017); A2;,
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