Category: indolines-derivatives

Related Products 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 (1. 2 MMOL) was dissolved in DCM (8 ML), treated with pyridine (2. 4 MMOL) and cooled to 0C. MESO2CI (1. 3 mmol) was added dropwise and the mixture allowed to stir at room temperature overnight. 0. 5 M HCI solution (10 ML) was added and the mixture extracted twice with DCM (10 ml) and twice with EtOAc (10 ML). The combined organics were washed with brine, dried over NA2SO4 and evaporated. The dried residue was dissolved in MeOH (5 ml) and THF (4 ml). Pd/C (100 mg) was added and the mixture stirred under an atmosphere of hydrogen at room temperature for 5 h. The mixture was filtered through a pad of Celite, which was washed with plenty of MeOH and EtOAc. The filtrate was concentrated in vacuum and the residue dried. The crude 6-amino indoline derivative and 4, 6-dichloropyrimidine (1. 5 MMOL) were dissolved in isopropanol (6 ml) and conc. HCI (0. 4 ml) and the mixture heated to reflux for 2. 5 h. For precipitation of the intermediate product the mixture was stored in the fridge overnight. The precipitate (HCI salt) was filtered, washed with a small quantity of cold isopropanol and dried. The intermediate (0. 17 MMOL), the corresponding phenylboronic acid (0. 2 mmol), Na2CO3 (0. 58 mmol) and Pd (PPh3) 2CI2 (3 mol%) were suspended in a mixture of DME/ETOH/WATER (1. 5 ML/0. 3 ML/0. 2 ML). The mixture was heated in the microwave at 125C for 1200 s. H20 (30 ml) was added and the mixture extracted twice with EtOAc (40 ML). Saturated NH4CI solution (20 ml) was added to the water phase and extracted again twice with EtOAc (40 ml). The combined organics were washed with brine and dried over NA2SO4. After evaporation of the solvent the residue was taken up in DMSO and purified via prep.-HPLC (XTerra Prep. MS C18 5 um, 19 X 150 mm, gradient from water to MeCN over 13 min).

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; AXXIMA PHARMACEUTICALS AG; WO2005/26129; (2005); A1;,
Indoline – Wikipedia,
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. 39603-24-2, name is 5,7-Dimethylindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Safety of 5,7-Dimethylindoline-2,3-dione

General procedure: In a 25 cm3 round bottom flask, to a mixture of isatin(1 mmol), malononitrile (2 mmol), and cyclohexanone (1 mmol) in 10 cm3 30 % ethanol, DABCO (20 mol%)was added. The reaction mixture was stirred at room temperature for time mentioned in Table 2 until completionof reaction, monitored by TLC. After completion ofreaction, the mixture was cooled and filtered to furnish thedesired product in good yields.

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 39603-24-2.

Reference:
Article; Hegade, Pravin G.; Chinchkar, Sarika D.; Pore, Dattaprasad M.; Monatshefte fur Chemie; vol. 147; 7; (2016); p. 1243 – 1249;,
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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. 20870-78-4, name is 5-Bromoindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 5-Bromoindolin-2-one

Compound 43a (5 g, 23.7 mmol) was dissolved in 150 mL THF.Sodium carbonate (25 g, 23.5 mmol) and di-tert-butyl dicarbonate (12.8 g, 58.6 mmol) were added in that order.Reaction at 60 C for 12 h,After completion of the reaction, the mixture was filtered and purified by silica gel column chromatography to afford compound 43b (3.1 g).

According to the analysis of related databases, 20870-78-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sichuan Kelun Botai Bio-pharmaceutical Co., Ltd.; Zhu Jiawang; Cai Jiaqiang; Li Guiying; You Zejin; Wu Yongyong; Han Runfeng; Ge Yong; Wang Lichun; Wang Jingyi; (49 pag.)CN109928979; (2019); A;,
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Related Products of 118289-55-7, 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 118289-55-7 as follows.

General procedure: A mixture of 6-chloro-5-(2-chloroethyl)-1,3-dihydro-2H-indol-2-one 1 (1.00mol), potassium carbonate (1.20mol), secondary amine (2a-h, 1.30mol) in water (10mL) was refluxed until completion (TLC, about 24-48h) and the reaction mass was cooled to RT and then extracted with DCM to get crude 3a-h. Recrystallized using aqueous acetone or aqueous ethanol or methanol (Yield 55-70%).

According to the analysis of related databases, 118289-55-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Meti, Gangadhar Y.; Kamble, Atulkumar A.; Kamble, Ravindra R.; Somagond, Shilpa M.; Devarajegowda; Kumari, Sandhya; Kalthur, Guruprasad; Adiga, Satish K.; European Journal of Medicinal Chemistry; vol. 121; (2016); p. 221 – 231;,
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Indoline | C8H9N – PubChem

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. Recommanded Product: 1-Methylindolin-2-one

Step 2; Preparation of 1-methyl-5-nitro-1,3-dihydro-indol-2-one; 1-Methyl-1,3-dihydro-indol-2-one (Step 1, 2.10 g, 14.3 mmol) is added in portions to 70% nitric acid (10 ml) at -10 C. After the addition is complete, the reaction is allowed to warm to room temperature and then stirred for 5 hours. The mixture is diluted with ice water and the resulting precipitate filtered, washed with water, and dried under a vacuum to give the title compound as a brown solid. HPLC r.t. 3.97 min; MS for C9H8N2O3 m/Z 193.9(M+H)+.

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

Reference:
Patent; Josyula, Vara Prasad Venkata Nagendra; Luehr, Gary; Gordeev, Mikhail; US2006/229348; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 5332-26-3, A common heterocyclic compound, 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, molecular formula is C9H6BrNO2, 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.

3.5 g (87 mmol) of sodium hydride are added portionwise to a solution of 25 g (87 mmol) of dimethyl 2-(4-tert-butoxycarbonylpiperazin-1-yl)malonate in 250 ml of tetrahydrofuran cooled to 2 C. The reaction medium is stirred at ambient temperature for 30 minutes and then brought back to 2 C., before adding, dropwise, 21 g (87 mmol) of 2-bromomethylisoindole-1,3-dione in 200 ml of tetrahydrofuran. The reaction medium is stirred at ambient temperature for 20 h, treated by adding 500 ml of water and then extracted with ethyl acetate. The organic phase is dried over magnesium sulfate, filtered, and concentrated under vacuum. [0193] The crude product obtained is purified by chromatography on silica gel, elution being carried out with a 70/30 heptane/ethyl acetate mixture. 27.5 g (73%) of dimethyl 2-(4-tert-butoxycarbonylpiperazin-1-yl)-2-(1,3-dioxo-1,3-dihydroisoindol-2-ylmethyl)malonate are obtained in the form of a white solid.

The synthetic route of 5332-26-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GALDERMA RESEARCH & DEVELOPMENT; MOUNIER, Carine; Carlavan, Isabelle; Aubert, Jerome; Jomard, Andre; Rossio, Patricia; US2014/275108; (2014); A1;,
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Indoline | C8H9N – PubChem

Electric Literature of 17702-83-9, 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. 17702-83-9, name is 2-(8-Bromooctyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Procedure M1. A mixture of the appropriate 2-(bromoalkyl)isoindoline-1,3-dione (1 equiv) with amine (pyrrolidine or morpholine) (1.1 equiv) in the presence of K2CO3 (3 equiv) was stirred in acetonitrile under reflux for 20 h. Subsequently, the solvent was evaporated under reduced pressure,producing a residue which was further dissolved in 20 mL of water and extracted with DCM(3 x 30 mL). The organic layer was dried with anhydrous Na2SO4. The solvent was then evaporated and the residue was purified by silica gel column chromatography (S3) yielding a yellow oil. The finalproduct was transformed into hydrochloride salt. The following compounds were obtained.

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-(8-Bromooctyl)isoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Hebda, Michalina; Bajda, Marek; Wieckowska, Anna; Szal?aj, Natalia; Pasieka, Anna; Panek, Dawid; Gody?, Justyna; Wichur, Tomasz; Knez, Damijan; Gobec, Stanislav; Malawska, Barbara; Molecules; vol. 21; 4; (2016);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 5332-26-3,Some common heterocyclic compound, 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-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: The benzofused N-heteroaromatic alkynes 2, 5, and 8 weresynthesized by reacting benzimidazole (1.0 mmol),benzotriazole (1.0 mmol), or carbazole (1.0 mmol) withpropargyl bromide (1.2 mmol) in the presence of potassiumcarbonate (2.0 mmol) using dimethylformamide bycontinuous stirring at 10-25 C up to 8-10 h [32]. For thesynthesis of target compounds, solution of aromatic bromides(1.0 mmol) in dimethylformamide was taken in around-bottomed flask and aqueous solution of sodium azide(3.0 mmol) was added, thereafter, stirred the reactionmixture for 1 h at 25-40 C. To the above reaction mixture,benzofused N-heteroaromatic alkyne 2 (1.0 mmol), 5(1.0 mmol), or 8 (1.0 mmol) was added followed by coppersulfate pentahydrate (5 mol %) and sodium ascorbate(10 mol %) [33], then, stirred the reaction contents overnight.The progress of reaction was monitored by thin layerchromatography. After the completion of reaction, ice-colddistilled water was added to the reaction mixture andproduct was extracted with ethyl acetate (50 cm3 9 3).The organic layer was washed with aqueous ammoniasolution followed by brine solution and dried using anhydroussodium sulfate. Filtered and evaporated the solventunder vacuum to get crude product which was furtherpurified by column chromatography using hexane:ethylacetate (7:3) as eluent.

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

Reference:
Article; Kaushik; Kumar, Krishan; Lal, Kashmiri; Narasimhan, Balasubramanian; Kumar, Ashwani; Monatshefte fur Chemie; vol. 147; 4; (2016); p. 817 – 828;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 7223-50-9, A common heterocyclic compound, 7223-50-9, name is N-Propargylphthalimide, molecular formula is C11H7NO2, 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.

General procedure: A mixture of a terminal alkyne (2.0 mmol), paraformaldehyde (180.2 mg, 2.0 mmol), amine (2 mmol) and Pt/TiO2 (5.0 mg, 0.25 mol%) loaded in distilled H2O (3 mL) and heated under microwave condition at 140 C and 250 W for appropriate reaction time (the reaction was monitored by TLC). After the completion of the reaction, the mixture was allowed to cool down and then extracted with EtOAc (3*20 mL). The combined organic extracts were dried (MgSO4) and fltered. The solvent was evaporated under reduced pressure and the resulting crude product was purifed by column chromatography (silica gel) to obtain the corresponding products 4a-4l.

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:
Article; Mohamed, Yasser M. A.; El Nazer, Hossam A.; Solum, Eirik Johansson; Chemical Papers; vol. 73; 2; (2019); p. 435 – 445;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 18711-13-2, A common heterocyclic compound, 18711-13-2, name is 4,7-Dichloroindoline-2,3-dione, molecular formula is C8H3Cl2NO2, 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 II-96 : (2-Oxo-1, 2-dihydro-pyrimidin-5-yl)-acetic acid [(3Z)-4,7-dichloro-2-oxo-1,2- DIHYDRO-INDOL-3-YLIDENE]-HYDRAZIDE [0639] The (at)TURE OF (2-OXO-1,2-DIHYDRO-PYRIMIDIN-5-YL)-ACETIC ACID HYDRAZIDE (67 MG, 0. 4 mmol) and 4,7-dichloro-isatin (95 mg, 0.44 mmol) in AcOH (10 mL) was stirred at 100″C FOR 3 h. After removal of the solvent, the residue was CRYSTALLIZED FROM MEOH TO GIVE THE TITLE compound as yellow solid (45 mg, 31%). [0640] H-NMR (400 MHz, DMSO-d6) 612. 68 (s, 1H), 11.92 (s, 1H), 8.41 (s, 2H), 7.46 (d, 1H), 7.16 (d, 1H), 4.00 (s, 2 H); MS (m/z) 366 [M+1].

The synthetic route of 18711-13-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUGEN, INC.; WO2005/5378; (2005); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem