Category: indolines-derivatives

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. 59-48-3, name is Indolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H7NO

5-Bromo-2-oxindole 2-Oxindole (1.3 g) in 20 ML acetonitrile was cooled to -10 C. and 2.0 g N-bromosuccinimide was slowly added with stirring.. The reaction was stirred for 1 hour at -10 C. and 2 hours at 0 C. The precipitate was collected, washed with water and dried to give 1.9 g (90% yield) of the title compound.

According to the analysis of related databases, 59-48-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sugen, Inc.; US6350754; (2002); B2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 102359-00-2,Some common heterocyclic compound, 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, 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.

General procedure: To a solution of 4 (1.77 g, 10 mmol) in 120 mL ofdichloromethane and 10 mL of DMF was added 4-methylmorpholine or DIEA (10 mL), TBTU (4.81 g, 15mmol) and aniline derivatives (11 mmol). The mixture wasstirred under room temperature for 18 h and washed in turnwith 5% sodium carbonate solution, 5% citric acid solutionand saturated sodium chloride solution. After dried byanhydrous sodium sulfate, the organic layer was evaporatedto dryness. The residue was purified with flash chromatography(CH2Cl2:CH3OH, 50:1) to afford intermediates 5a-5l, which were used in the next step in short time. To asolution of compounds 5a-5l (1.0 mmol) in 10 mL methanolwas added piperidine (30 muL) and 1H-pyrrole-2-carbaldehyde/furan-2-carbaldehyde (1.0 mmol). The mixturewas stirred at 60 C for 5 h and cooled to room temperature.After kept in fridge overnight, the target compounds 6a-6land 7a-7l were obtained in high yields.

The synthetic route of 102359-00-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ai, Juntao; Lv, Meng; Li, Xiaohui; Chen, Zhuo; Hu, Gaoyun; Li, Qianbin; Medicinal Chemistry Research; vol. 27; 1; (2018); p. 161 – 170;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 181140-34-1, name is (R)-(-)-N-(2,3-Epoxypropyl)phthalimide, A new synthetic method of this compound is introduced below., Product Details of 181140-34-1

General procedure: Compounds 2-5 were synthesized using a modified procedure originally reported by Roehrig et al.28 To a cooled solution of (R)-(-)-N-(2,3-epoxypropyl)phthalimide 1 (102 mg, 0.50 mmol) in 10 mL of 2-propanol, amine or aminoalcohol (0.6 mmol, 1.2 equiv) in 10 mL of 2-propanol was added at 0 C and stirred for 1 h. It was then refluxed for 8 h. After the completion of the reaction, the solvent was removed under reduced pressure and the crude product was purified by flash chromatography on silica gel (CHCl3/MeOH 1:20 as eluent) to afford 2-5 as white crystals.

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; Bozkurt, Selahattin; Durmaz, Mustafa; Naziroglu, Hayriye Nevin; Yilmaz, Mustafa; Sirit, Abdulkadir; Tetrahedron Asymmetry; vol. 22; 5; (2011); p. 541 – 549;,
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. 603-62-3, name is 3-Nitrophthalimide, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H4N2O4

Example 25Preparation of l-[(lalpha,5alpha,6alpha)-3-(2,4-difluorophenyl)-3-azabicyclo[3.1.0]hex-6-yl]-3-(2- methyl-l,3-dioxo-2,3-dihydro-l//-isoindol-4-yl)urea:Step 1: 2-methyl-4-nitro-lH-isoindole-l,3(2H)-dione:To a stirred solution of 4-nitro-lH-isoindole-l,3(2H)-dione (0.00520 mole) in DMF (5 mL), NaH (0.000528 mole) is added at O0C and stirred the reaction mixture at RT for 30 min. To the above at 00C, methyl iodide (0.000528 mole) is added and stirred for 2 h at room temperature. On completion of reaction, the reaction mixture is quenched with water, extracted with ethyl acetate and the organic layer dried and concentrated to get the desired product. 1H NMR (DMSO- d6): delta 3.04 (s, 3H); 8.04 (t, IH, J = 9 Hz); 8.14 (d, IH, J = 9 Hz); 8.25 (d, lH, J = 6 Hz).

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 603-62-3.

Reference:
Patent; GLENMARK PHARMACEUTICALS, S.A.; WO2009/90548; (2009); A2;,
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. 24566-79-8, name is N-(6-Bromohexyl)phthalimide, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C14H16BrNO2

To a stirred solution of compound 3-i (6.39 g, 20.3 mol) in DMF (60 mL) was added potassium thioacetate (2.78 g, 34.3 mmol) portion wise and stirred for 20 min at room temperature. After complete addition, the reaction mixture was stirred at room temperature for 30 min. Reaction progress was monitored by TLC; after completion the reaction mixture was quenched with ice-cold water (250 mL) and stirred for 1 h. The resultant precipitated was filtered, washed with water (100 mL) and dried in vacuo to afford 4-i as an off-white solid (5.8 g, 93.5%). LCMS: 306.20 (M+l).

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 24566-79-8.

Reference:
Patent; CV6 THERAPEUTICS (NI) LIMITED; SPYVEE, Mark; (500 pag.)WO2018/98206; (2018); 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. 1035235-27-8, name is tert-Butyl 4-bromoisoindoline-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 1035235-27-8

Step 5: tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-dihydro-2H-isoindole-2-carboxylate A solution of tert-butyl 4-bromo-1,3-dihydro-2H-isoindole-2-carboxylate (0.80 mmol), bis(pinacolato)diboron (0.96 mmol) and potassium acetate (2.5 mmol) in DMF (4 mL) was degassed. To this solution was added PdCl2dppf (1:1 complex with DCM, 0.04 mmol). The reaction mixture was heated at 85 C. for 4 hr and then allowed to cool to rt and diluted with EtOAc. The solution was washed with water and brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-dihydro-2H-isoindole-2-carboxylate (0.64 mmol, 80%) as a white solid. LCMS: (FA) ES+346.

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 1035235-27-8.

Reference:
Patent; Millennium Pharmaceuticals, Inc.; US2008/171754; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 102359-00-2, These common heterocyclic compound, 102359-00-2, name is 2-Oxoindoline-5-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.

To a solution of 2-oxoindoline-5-carboxylic acid (0.200 g, 1.12 mmol), 1- [3- (dimethylamino) propyl] -3-ethylcarbodiimide hydrochloride (0.477 g, 2.47 mmol), diisopropylethylamine (0.586 mL, 3.37 mmol) and catalytic amount of N, N- dimethylaminopyridine in N, N-DIMETHYLFORMAMIDE/ACTEONITRILE (1: 1,4 mL) was added 2- methoxybenzylamine (0.295 mL, 2.26 mmol) and the reaction mixture stirred at room temperature for 1 h. The solvent was evaporated and the crude material was purified on a short silica gel column using dichloromethane containing 5% methanol as the eluent. This was followed by triturating from ethyl acetate to give 0.10 g (33% yield) of the yellow title compound : 1H NMR (DMSO-d6,400 MHz) 8 10.60 (br s, 1 H), 8.65 (t, J = 6 Hz, 1 H), 7.79-7. 77 (m, 2 1-1), 7.21 (t, J = 8 Hz, 1 H), 7.15 (d, 7= 8 HZ, 1 H), 6. 98 (d, J = 8 Hz, 1 H), 6.90-6. 84 (m, 2 H), 4.42 (d, J = 6 Hz, 2 H), 3.81 (s, 3 H), 3.53 (s, 2 H) ; MS (ES) m/z 297 (M++1), NILZ 295

The synthetic route of 102359-00-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2005/27823; (2005); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 3676-85-5, name is 5-Aminoisoindoline-1,3-dione, 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 3676-85-5, Recommanded Product: 3676-85-5

At room temperature,In a 25mL reaction bottle,Join in order3-aminophthalic acid imide(0.5 mmol), diphenylphosphoryl (1 mmol),TEMPO (0.05 mmol), and tetrahydrofuran 48 mmol, 2 mL), mixed evenly,The reaction is then heated to 40 C.The reaction was stirred for 12 hours.After the reaction was completed by TLC, pure water was added.Then add ethyl acetate for 3 times.The extracts are combined and the extract is dried over anhydrous sodium sulfate.The extract was concentrated under reduced pressure in vacuo (0.08 Mpa) to dryness to afford crude material.Then rinse with a mixed eluent of 3:1 by volume of petroleum ether and ethyl acetate.Silica gel column flash column chromatography,Obtaining the product of Example 4o,It was 152 mg of a yellow solid, yield 70%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Aminoisoindoline-1,3-dione, and friends who are interested can also refer to it.

Reference:
Patent; Qufu Normal University; Wei Wei; Huang Qiang; Lv Yufen; Liu Qishun; (20 pag.)CN109942627; (2019); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 868066-91-5, name is 5-Bromo-2-methylisoindolin-1-one, A new synthetic method of this compound is introduced below., SDS of cas: 868066-91-5

(E)-Ethyl 3-(2-methyl-1-oxoisoindolin-5-yl)acrylateA mixture of tri-o-tolylphosphine (0.242 g, 0.796 mmol), ethyl acrylate (1.594 g, 15.92 mmol), 5-bromo-2-methylisoindolin-1-one (1.8 g, 7.96 mmol), Pd(OAc)2(0.089 g, 0.398 mmol), and TEA (2.220 mL, 15.92 mmol) in CH3CN (25.0 mL) was stirred at 80 °C for 3 h. The reaction was filtered and concentrated and the residue was purified by flash column chromatography eluting with petroleum ether/EtOAc (1/5), to afford (E)-ethyl 3-(2- methyl-1-oxoisoindolin-5-yl)acrylate (1.02 g, 3.95 mmol, 49.6 percent yield). LC-MS: m/z 247 (M+H)+1.50 min (ret. time).

The synthetic route of 868066-91-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ASTEX THERAPEUTICS LIMITED; BOEHM, Jeffrey Charles; DAVIES, Thomas Glanmor; WOOLFORD, Alison Jo-anne; GRIFFITHS-JONES, Charlotte Mary; WILLEMS, Hendrika Maria Gerarda; NORTON, David; SAXTY, Gordon; HEIGHTMAN, Thomas Daniel; LI, Tindy; KERNS, Jeffrey K.; DAVIS, Roderick S.; YAN, Hongxing; WO2015/92713; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 13861-75-1, name is Spiro[cyclopropane-1,3′-indolin]-2′-one, 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 13861-75-1, Application In Synthesis of Spiro[cyclopropane-1,3′-indolin]-2′-one

Bromine (0.15 mL, 3.0 mmol) was added drop-wise to a mixture of spiro[cyclopropane-1,3′-[3H]indol]-2′(1’H)-one (486 mg, 3.05 mmol), 174 muL (3.0 mmol) acetic acid (0.174 mL, 3.0 mmol) and sodium acetate (250 mg, 3.0 mmol) in dry dichloromethane (120 mL). After 4 h, the reaction was washed with 5% sodium thiosulfalte and brine. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give 5′-bromospiro[cyclopropane-1,3′-indol]-2′(1’H)-one (0.75 g, 100%) as a white solid. This compound was used without further purification.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Wyeth; US2006/30615; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem