Category: 496-12-8

Electric Literature of 496-12-8, 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. 496-12-8, name is Isoindoline, This compound has unique chemical properties. The synthetic route is as follows.

A solution of 5-bromo-2,4-dihydroxy-benzoic acid (520 mg, 2.33 mmol) in DMF (5 mL) was treated with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (471 mg, 2.45 mmol) then HOBt (362 mg, 2.68 mmol). After 25 min, 2,3-dihydro-1H-isoindole (0.5 mL, 2.63 mmol) was added then the mixture was stirred at r.t. for 18 h. The solvent was removed in vacuo then the residue was taken up in ethyl acetate and washed with 1N hydrochloric acid, saturated sodium bicarbonate solution and brine then dried (MgSO4) and concentrated. The residue was triturated with methanol to afford the title compound as a grey solid (328 mg, 44%). 1H NMR (DMSO-d6) 10.45 (1H, s), 10.32 (1H, s), 7.36 (1H, br. s), 7.35 (1H, s), 7.28 (3H, br. s), 6.59 (1H, s), 4.77 (2H, br. s), 4.71 (2H, br. s). MS: [M+H]+ 332/334.

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

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; US2010/152184; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 496-12-8, 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 496-12-8 as follows.

A 1.0 g (8.4 mmol) amount of isoindoline was dissolved in 25 mL of acetonitrile. After addition of potassium carbonate (2.3 g, 16.8 mmol), the resulting mixture was heated at 70 C. After 30 min, the solution was allowed to cool to room temperature. A 4.2 mL (47.2 mmol) amount of 1-bromo-3-chloropropane was added and the reaction mixture stirred at room temperature for 24 h. The solvent was removed under reduced pressure and 60 mL water added to the residue. The product was extracted with 3¡Á30 mL dichloromethane. The combined organic fractions were washed with water and dried over sodium sulphate. The solvent was evaporated under reduced pressure. Purification by column chromatography (DCM:MeOH(NH3), 99:1 (v/v)) was performed and enabled collection of the product as a brown liquid (1.27 g, 77%). TLC: Rf 0.7 (DCM:MeOH(NH3), 9:1, v/v). 1H NMR (300MHz, CDCl3) delta: 7.21 (s, 4H, Haro); 3.95 (s, 4H, 2 CH2); 3.69 (t, 3J=7Hz, 2H, CH2); 2.90 (t, 3J=7Hz, 2H, CH2); 2.07 (p, 3J=7Hz, 2H, CH2). 13C NMR (75MHz, CDCl3) delta: 140.0 (2Caro); 126.7 (2Caro); 122.3 (2Caro); 59.1 (2CH2); 53.0 (CH2); 43.1 (CH2); 31.9 (CH2). LCMS (ESI+): Calc. for [M+H]: 196.05; 198.07. Found: 195.95; 197.91.

According to the analysis of related databases, 496-12-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Donnier-Marechal, Marion; Carato, Pascal; Le Broc, Delphine; Furman, Christophe; Melnyk, Patricia; European Journal of Medicinal Chemistry; vol. 92; (2015); p. 575 – 582;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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, Quality Control of Isoindoline

The above compound was prepared as follows using General Procedure G9. lsoindoline (130 mg, 1 mmol) was added to a solution of 3-chloro-4,6-dimethoxy-2- methylbenzoic acid (compound A in general procedure G9, and prepared via the method reported by Clevenger et al. Organic Letters (2004), 6(24), p4459)) (200 mg, 0.87 mmole), diisopropylethyl amine (0.8 mL, 4.5 mmol), and O-(7-azabenzotriazol-1 -yl)-N,N,N’,N’- tetramethyluronium phosphorus pentafloride (HATU) (380 mg, 1 mmol) in 4 mL of DMF under a nitrogen atmosphere. The reaction was allowed to stir at room temperature for 12 hours. Saturated NaHCO3 (30 mL) was added to the reaction mixture to quench the reaction. EtOAc EPO (2 x 50 ml.) was then added to extract the aqueous solution. Dry EtOAc layer over Na2SO4. The Na2SO4 was filtered off and the filtrate was evaporated to give a brown oil residue. The residue was purified by silica gel chromatography (gradient elution 45 ?50% EtOAc in hexanes) to give the desired intermediate product (3-chloro-4,6-dimethoxy-2- methylphenyl)(isoindolin-2-yl)methanone (265 mg, 92% yield). 1H NMR (400 MHz, DMS0-D6) delta ppm 2.18 (s, 3 H) 3.81 (s, 3 H) 3.92 (s, 3 H) 4.39 (d, J=7.07 Hz, 2 H) 4.80 (s, 2 H) 6.76 (s, 1 H) 7.17 – 7.35 (m, 3 H) 7.38 (d, J=7.07 Hz, 1 H): Anal. Calcd for C18H18CINO3: C, 65.16; H, 5.47; N, 4.22. Found: C, 65.05; H, 5.48; N, 4.22.

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; PFIZER INC.; WO2006/117669; (2006); A1;,
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. 496-12-8, name is Isoindoline, A new synthetic method of this compound is introduced below., Recommanded Product: Isoindoline

Under N2, at 0 0C, trichloroacetyl chloride (0.57 mL, 5.0 mmol) was added dropwise to a stirring solution of isoindoline (1.0 g, 5.0 mmol), Et3N (0.7 mL, 0.51 g, 5.0 mmol) and CH2Cl2 (20 mL). The solution was allowed to warm to room temperature and stirred for 1 h. After evaporating the solvents in vacuo, the mixture was purified via silica EPO gel chromatography using 8:2 hexanes/EtOAc to obtain the desired amide (1.2 g, 4.6 mmol, 91% yield). LC/MS (10-99% CH3CN), M/Z: M+l obs = 265.9; tR = 3.51 min.

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; VERTEX PHARMACEUTICALS INCORPORATED; WO2006/122014; (2006); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 496-12-8,Some common heterocyclic compound, 496-12-8, name is Isoindoline, molecular formula is C8H9N, 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 stirred solution of Boc-2,4-dichloro-d-phenylalanine (0.280 g, 0.84 mmol), EDC¡¤HCl (0.161 g, 0.84 mmol), HOBt (0.170 g, 1.26 mmol) and DIPEA (1.12 mL, 6.29 mmol) in DMF (2.0 mL), isoindoline (0. 10 g, 0.84 mmol) was added. The reaction was stirred at room temperature for 24 h. Upon completion, solvent was removed under reduced pressure and the crude was purified using column chromatography to provide desired coupled product in 78% yield. To the purified compound (0.21 g, 0.48 mmol) was added 1 M HCl (9.5 mL, 1 M in Et2O). After 4 h of stirring, the solvent was removed under reduced pressure to afford target compound 4 as a white solid. 1H NMR (400 MHz, CD3OD): delta 3.42 (d, 2H, 8.0 Hz), 4.24 (d, 1H, 12 Hz), 4.63 (t, 1H, 8.0 Hz), 4.72 (d, 1H, 16 Hz), 4.89 (d, 1H, 16 Hz), 5.00 (d, 1H, 12 Hz), 7.26 (m, 1H), 7.35 (m, 4H), 7.44 (d, 1H, 8.0 Hz), 7.54 (d, 1H, 4.0 Hz) 13C NMR (100.6 MHz, CD3OD): delta 35.3, 52.1, 53.2, 53.6, 123.7, 123.9, 128.9, 129.1, 129.2, 130.7, 132.1, 132.4, 136.0, 136.3, 136.4, 136.6, 168.1 HRMS (TOF-MS) Exact mass calcd for C17H16Cl2N2O [M+H]+: 335.0718, found: 335.0712.

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

Reference:
Article; Whitehead, Lewis; Dobler, Markus R.; Radetich, Branko; Zhu, Yanyi; Atadja, Peter W.; Claiborne, Tavina; Grob, Jonathan E.; McRiner, Andrew; Pancost, Margaret R.; Patnaik, Anup; Shao, Wenlin; Shultz, Michael; Tichkule, Ritesh; Tommasi, Ruben A.; Vash, Brian; Wang, Ping; Stams, Travis; Bioorganic and Medicinal Chemistry; vol. 19; 15; (2011); p. 4626 – 4634;,
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. 496-12-8, name is Isoindoline, A new synthetic method of this compound is introduced below., Product Details of 496-12-8

To a solution of isoindoline (335 mg, 2.8 mmol) in DCM (5 ml) is added a 2M solution of trimethylaluminum in toluene (1.4 ml, 2.8mmol) and the resulting solution is allowed to EPO stir at ambient temperature for 30 minutes and is then added to a solution of 2-tert- butoxycarbonylamino-3-(2-chloro-3,4-dimethoxy-phenyl)-propinoic acid methyl ester (520 mg, 1.39 mmol) in DCM (5 ml). The reaction is allowed to stir at ambient temperature for 18 h and carefully quenched with a 10% aqueous solution of citric acid. The resulting biphasic mixture is diluted with DCM (20 ml) and extracted with a saturated solution of Rochelle’s Salt (20 ml). The organic layer is separated, concentrated in vacuo and purified by column chromatography (hexanes-ethyl acetate 15- 60%) resulting in 2-tert-Butoxycarbonylamino -3-(2-chloro-3,4-dimethoxy-phenyl)-l-(l,3-dihydro- isoindol-2-yl)-propan-l-one (300 mg, 47%). 2-tert-Butoxycarbonylamino -3-(2-chloro-3,4- dimethoxy-phenyl)-l-(l,3-dihydro-isoindol-2-yl)-propan-l-one is analyzed by HPLC/Mass Spec.

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; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2007/38459; (2007); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 496-12-8, These common heterocyclic compound, 496-12-8, name is Isoindoline, 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.

Isoindoline 228 Milligram (mg) ( (1.91 mmol, mmol) was dissolved in dimethylformamide Dissolved in 20 milliliters (mL) 153 mg of 55% (v / v) sodium hydride at 0 C (3.52 mmol) was added thereto, followed by stirring for about 40 minutes, 3 – ((2S, 3R, 4R, 5S, 6R) -3,4,5-triacetoxy-6-acetoxymethyl-tetrahydropyran -2-yl] benzyl bromide 800 mg (1.60 mils Mol) was added and the mixture was stirred at room temperature for about 10 hours. 100 milliliters of water was added to the reaction mixture, and the mixture was extracted with ethyl acetate Dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by column chromatography to give 420 mg (yield: 70.7%) of the title compound was obtained.

The synthetic route of 496-12-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Samjin Pharmaceutical Co., Ltd.; Cho, Eui-Hwan; Shin, Hui-Jong; Kwon, Ho-Seok; Lee, Jae-Woong; Joo, Jeong-Ho; Lee, Keun-Kuk; Kim, Jong-Min; Kim, Hyun-Tae; Kim, Jae-Eon; Lee, Jung-Rok; Jang, Beom-Hyeon; (37 pag.)KR2016/97861; (2016); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 496-12-8, 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 496-12-8 as follows.

A solution of 5-bromo-2,4-dihydroxy-benzoic acid (520 mg, 2.33 mmol) in DMF (5 mL) was treated with 1-(3-dirnethylaminopropyl)-3-ethylcarbodiimide hydrochloride (471 mg, 2.45 mmol) then HOBt (362 mg, 2.68 mmol). After 25 min, 2,3-dihydro-1 H-isoindole (0.5 mL, 2.63 mmol) was added then the mixture was stirred at r.t. for 18 h. The solvent was removed in vacuo then the residue was taken up in ethyl acetate and washed with 1 N hydrochloric acid, saturated sodium bicarbonate solution and brine then dried (MgSO4) and concentrated. The residue was triturated with methanol to afford the title compound as a grey solid (328 mg, 44%). 1H NMR (DMSO-d6) 10.45 (1 H, s), 10.32 (1H, s), 7.36 (1H, br.s), 7.35 (1 H1 s), 7.28 (3H, br.s), 6.59 (1H1 s), 4.77 (2H1 br.s), 4.71 (2H1 br.s). MS: [M+H]+ 332/334.

According to the analysis of related databases, 496-12-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; WO2008/44045; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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 496-12-8 as follows. HPLC of Formula: C8H9N

EXAMPLE 1 Preparation of (1,3-Dihydro-isoindol-2-yl)-(2-isopropoxy-5-methanesulfonyl-phenyl)-methanone; A mixture of 0.387 mmol 2-isopropoxy-5-methanesulfonyl-benzoic acid (example B1), 0.464 mmol 2,3-Dihydro-1H-isoindole (commercial), 0.426 mmol TBTU and 1.935 mmol DIPEA in 1.4 ml DMF was stirred at RT for 2 h. The reaction mixture was evaporated in vacuo. The residue was taken in water and extracted with ethylacetate. The combined organic phases were washed with saturated sodium bicarbonate solution, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by chromatography (SiO2, heptane/ethyl acetate) to yield the title compound as a light brown solid (88% yield). MS (m/e): 360.2 [M+H]+, 100%)

According to the analysis of related databases, 496-12-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Jolidon, Synese; Narquizian, Robert; Norcross, Roger David; Pinard, Emmanuel; US2006/178381; (2006); 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. 496-12-8, name is Isoindoline, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 496-12-8

DIPEA (30 mg, 0.22 mmol, 1.1 eq) was added to a solution of triazine 4b (94 mg, 0.2 mmol, 1 eq) in CH2Cl2 (3 mL) cooled in an ice water bath. After 5 min, a solution of isoindoline (28 mg, 0.22 mmol, 1.1 eq) in CH2Cl2 (1 ml) was added dropwise for 5 min at 0C. The mixture was then stirred for 72 h at room temperature, concentrated under reduced pressure and purified by column chromatography on silica gel (CH2Cl2) to afford 81mg (99 %) of Mel31. 1H NMR: (400 MHz, CDCl3) delta 7.29 (4H, br s, CHar), 5.14(1H, br s, NH), 4.99-4.69(4H, m, CH2-N -CH2), 3.00-2.83 (3H, m, CH3). LC-MS: m/z calcd. for C18 H12 F5 N5 O (M+H)+: 410.0967; found: 410.1040 .

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 496-12-8.

Reference:
Article; Djehal, Amel; Krayem, Mohammad; Najem, Ahmad; Hammoud, Hassan; Cresteil, Thierry; Nebigil, Canan G.; Wang, Dong; Yu, Peng; Bentouhami, Embarek; Ghanem, Ghanem E.; Desaubry, Laurent; European Journal of Medicinal Chemistry; vol. 155; (2018); p. 880 – 888;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem