Category: 480-91-1

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. 480-91-1, name is Isoindolin-1-one, A new synthetic method of this compound is introduced below., Quality Control of Isoindolin-1-one

General procedure: Isoindolin-1-one (200 mg, 1.50mmol) was dissolved in super-dry DMSO (4 mL), and Cs2CO3 (1215 mg, 3.75 mmol), CuI (58 mg, 0.30mmol) and N1,N2-dimethylethane-1,2-diamine (27 mg, 33 muL, 0.30 mmol) were added to the solution.The resulting mixture was stirred at room temperature for 10 min, after which iodobenzene (2.25mmol) was added. Then the mixture was heated to 120 C. When TLC showed that isoindolin-1-onehad been fully converted, the reaction was stopped. The mixture was extracted with ethyl acetate (20mL) and H2O (10 mL). The water phase was re-extracted with ethyl acetate (20 mL). The organic layerwas combined and washed with brine (10 mL). Then the solution was dried over anhydrous MgSO4,filtered and concentrated, and the crude residue was purified by flash chromatography over silica gelusing CH2Cl2/CH3OH as the gradient elution to afford the title compounds.

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; Wang, Yixuan; Wang, Huiqiang; Jiang, Xinbei; Jiang, Zhi; Guo, Tingting; Ji, Xingyue; Li, Yanping; Li, Yuhuan; Li, Zhuorong; Molecules; vol. 24; 5; (2019);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 480-91-1, These common heterocyclic compound, 480-91-1, name is Isoindolin-1-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.

A stirred mixture of 79D (4.6 g, 8.64 mmol), isoindolin-1-one (1.15 g, 8.64 mmol), Pd2(dba)3 (791 mg, 0.864 mmol), Cs2CO3 (8.44 g, 25.92 mmol) and Xantphos (700 mg, 1.21 mmol) in 1,4-dioxane (150 mL) was heated to 100 C. overnight. The reaction mixture was allowed to cool to room temperature and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by silica column chromatography (1%-5% MeOH in DCM) to give 79E (2.6 g, 56% yield) as a white solid: 1H NMR (400 MHz, DMSO-d6) delta 8.54 (d, J=8 Hz, 1H), 8.05 (t, J=7.6 Hz, 1H), 7.99 (d, J=6.8 Hz, 1H), 7.79 (d, J=7.6 Hz, 1H), 7.66 (t, J=7.2 Hz, 1H), 7.57-7.48 (m, 3H), 7.22 (t, J=7.6 Hz, 1H), 7.13-7.04 (m, 4H), 5.19 (d, J=7.2 Hz, 1H), 5.03 (d, J=17.6 Hz, 1H), 4.56 (d, J=17.6 Hz, 1H), 4.11 (dd, J=10.4 Hz, 3 Hz, 1H), 3.95 (d, J=9.2 Hz, 1H), 3.12-2.93 (m, 3H), 2.81-2.75 (m, 1H), 0.80 (s, 9H); ESI m/z 586.1 [M+H]+.

Statistics shows that Isoindolin-1-one is playing an increasingly important role. we look forward to future research findings about 480-91-1.

480-91-1, name is Isoindolin-1-one, 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. SDS of cas: 480-91-1

To a suspension of sodium hydride freshly-washed with hexane (450 mg, 11.26 mmol) in freshly-distille THF (25 mL) was slowly added a solution of isoindolin-1-one (1.00 g, 7.51 mmol) in THF (25 mL) under an N2 atmosphere at 0C and stirred for 30 min. To the resulting reaction mixture was added tert-butyl bromoacetate (1.66 mL, 11.26 mmol) and stirring was continued at room temperature (16 h). The reaction mixture was carefully quenched with methanol and concentrated to obtain a crude residue. The crude product was then further purified by column chromatography (hexanes/ethyl acetate, 4:1) to afford pure isoindolinone ester 2 as an off-white solid (1.80 g, 97%); mp = 62-64C; Rf = 0.33 (hexane/ethyl acetate, 2:1); FT-IR (neat) 2972, 2932, 1738, 1687 cm -1; 1H NMR (400 MHz, CDCl3) delta 7.87-7.85 (d, J = 7.6 Hz, 1H), 7.54-7.52 (m, 1H), 7.47-7.43 (m, 2H), 4.51 (s, 2H), 4.29 (s, 2H), 1.46 (s, 9H) ppm. 13C NMR (100 MHz, CDCl3) delta 168.8, 168.1, 141.6, 131.9, 131.6, 127.9, 123.9, 122.7, 82.2, 50.5, 44.5, 28.1 ppm. LRMS calcd for C14H17NO3 (M+H) 248, found 248.

The synthetic route of 480-91-1 has been constantly updated, and we look forward to future research findings.

Electric Literature of 480-91-1,Some common heterocyclic compound, 480-91-1, name is Isoindolin-1-one, molecular formula is C8H7NO, 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: Isoindolin-1-one (200 mg, 1.50mmol) was dissolved in super-dry DMSO (4 mL), and Cs2CO3 (1215 mg, 3.75 mmol), CuI (58 mg, 0.30mmol) and N1,N2-dimethylethane-1,2-diamine (27 mg, 33 muL, 0.30 mmol) were added to the solution.The resulting mixture was stirred at room temperature for 10 min, after which iodobenzene (2.25mmol) was added. Then the mixture was heated to 120 C. When TLC showed that isoindolin-1-onehad been fully converted, the reaction was stopped. The mixture was extracted with ethyl acetate (20mL) and H2O (10 mL). The water phase was re-extracted with ethyl acetate (20 mL). The organic layerwas combined and washed with brine (10 mL). Then the solution was dried over anhydrous MgSO4,filtered and concentrated, and the crude residue was purified by flash chromatography over silica gelusing CH2Cl2/CH3OH as the gradient elution to afford the title compounds.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Isoindolin-1-one, its application will become more common.

Synthetic Route of 480-91-1, The chemical industry reduces the impact on the environment during synthesis 480-91-1, name is Isoindolin-1-one, I believe this compound will play a more active role in future production and life.

Phthalimidine (800 mg, 6.01 mmol) was dissolved in THF(40 mL). At ambient temperature triethylamine (670 mg,6.62 mmol) was added dropwise and the mixture was stirred for5 min, whereupon dichlorophenylphosphine (538 mg, 3.01 mmol)was added and the mixture was stirred for one day. Thereafter thewhite precipitate was filtered and washed with THF (3 mL). Thecombined filtrate and washings were evaporated to dryness (condensationof volatiles into a cold trap under reduced pressure), theresidue was dissolved in THF (10 mL) and the solution was filteredthrough Celite. After vapor diffusion of n-pentane into the filtrate(for one week), white crystalline product suitable for single-crystalX-ray diffraction was obtained. The supernatant was removed bydecantation, the white solid was washed with n-pentane (3 mL)and dried in vacuo to yield 480 mg (1.29 mmol, 43%) of 1b.

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, Isoindolin-1-one, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Gericke, Robert; Wagler, Joerg; Polyhedron; vol. 125; (2017); p. 57 – 67;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 480-91-1,Some common heterocyclic compound, 480-91-1, name is Isoindolin-1-one, molecular formula is C8H7NO, 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.

[0195] To 2,3-dihydro-isoindol-l-one (250.Omg, 1.85mmol) in acetonitrile (9mL) was added propargyl bromide (308.6uL, 2.77mmol) and cesium carbonate (2.4g, 7.39mmol) and the mixture was allowed to stir at 80C for two hours. An aqueous workup was done to provide the title compound (303.3mg, 96%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Isoindolin-1-one, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; NPS PHARMACEUTICALS, INC.; WO2006/20879; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

480-91-1, name is Isoindolin-1-one, 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. Application In Synthesis of Isoindolin-1-one

Isoindolin-1-one 21 (250mg, 1.85mmol) was dissolved in acetonitrile (9mL) and cesium carbonate (2.40g, 7.39mmol) was added followed by propargyl bromide (308muL, 2.77mmol). The reaction mixture was stirred at reflux (2h). The reaction mixture was then dissolved in CH2Cl2 (10mL) and washed with water (3¡Á15mL). The organic layer was dried (Na2SO4), filtered and concentrated under reduced pressure. Gravity-column chromatography of the residual oil (hexane/ethyl/acetate, 2:1) gave 27 as a yellow solid (205mg, 65%): mp 79-81C; Rf 0.66 (ethyl acetate); 1H NMR (400MHz, CDCl3) delta 7.82 (dJ=8.0Hz, 1H), 7.52 (dd J=8.0, 7.2Hz, 1H) 7.41-7.45 (m, 2H), 4.47 (s, 2H), 4.24 (s, 2H), 2.28 (s, 1H). 13C NMR (100MHz, CDCl3) delta 167.9, 141.2, 132.1, 131.6, 128.1, 123.8, 122.8, 78.1, 72.5, 49.1, 31.7. IR (neat) 3290, 3243, 2118, 1701cm-1; HRMS (ESI-TOF) m/z [M+H]+; calculated for C11H10NO 172.0762, Found: 172.0857.

The synthetic route of 480-91-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ronnebaum, Jarrid M.; Luzzio, Frederick A.; Tetrahedron; vol. 72; 40; (2016); p. 6136 – 6141;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 480-91-1, These common heterocyclic compound, 480-91-1, name is Isoindolin-1-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.

General procedure: A solution of POCl3 or POBr3 (30 mmol) in anhydrous DCM (7 mL) was added dropwise to DMF or DMA (30 mmol) in anhydrous DCM (15 mL) at 0 C. The mixture was stirred for 30 min at room temperature. Then, a solution of 1H-isoindolinone 1 (2 g, 15 mmol) in anhydrous DCM (75 mL) was added to the mixture, at 0 C. Subsequently, the reaction mixture was heated at reflux for 5 h, and then after cooling, the solvent was removed at reduced pressure. Ice-water was added, and the mixture was neutralized with NaOH 5 M. The precipitate was filtered out, washed with water and dried. The residue was recrystallized from MeOH/H2O (1:1) to give the following compounds.

The synthetic route of 480-91-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Diana, Patrizia; Martorana, Annamaria; Barraja, Paola; Montalbano, Alessandra; Carbone, Anna; Cirrincione, Girolamo; Tetrahedron; vol. 67; 11; (2011); p. 2072 – 2080;,
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. 480-91-1, name is Isoindolin-1-one, This compound has unique chemical properties. The synthetic route is as follows., Safety of Isoindolin-1-one

To a solution of isoindolin-1-one (120 mg 0.90 mmol) in MeCN (10 mL) was added Cs2CO3 (652 mg, 2.0 mmol) and ethyl 2-iodo-4-methylpentanoate (540 mg, 2.0 mmol). The mixture was stirred at 85 C. for 12 hours and filtered. The filtrate was concentrated under pressure, and the residue was purified by silica gel column (petroleum ether_EtOAc=3:1) to give the desired product ethyl 4-methyl-2-(1-oxoisoindolin-2-yl)pentanoate as a colorless oil (120 mg). Yield 50% (95% purity, UV=254 nm, ESI 276.1 (M+H)+).

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 480-91-1.

Reference:
Patent; Morphic Therapeutic, Inc.; Bursavich, Matthew G.; Troast, Dawn M.; Harrison, Bryce A.; Lippa, Blaise S.; Rogers, Bruce N.; Konze, Kyle D.; Gerasyuto, Aleksey I.; Day, Tyler; Lin, Fu-Yang; Hahn, Kristopher N.; Svensson, Mats A.; Kim, Byungchan; Zhong, Cheng; Lugovskoy, Alexey A.; Sosa, Brian; (263 pag.)US2019/315692; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 480-91-1, 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 480-91-1 as follows.

General procedure: Isoindolin-1-one (200 mg, 1.50mmol) was dissolved in super-dry DMSO (4 mL), and Cs2CO3 (1215 mg, 3.75 mmol), CuI (58 mg, 0.30mmol) and N1,N2-dimethylethane-1,2-diamine (27 mg, 33 muL, 0.30 mmol) were added to the solution.The resulting mixture was stirred at room temperature for 10 min, after which iodobenzene (2.25mmol) was added. Then the mixture was heated to 120 C. When TLC showed that isoindolin-1-onehad been fully converted, the reaction was stopped. The mixture was extracted with ethyl acetate (20mL) and H2O (10 mL). The water phase was re-extracted with ethyl acetate (20 mL). The organic layerwas combined and washed with brine (10 mL). Then the solution was dried over anhydrous MgSO4,filtered and concentrated, and the crude residue was purified by flash chromatography over silica gelusing CH2Cl2/CH3OH as the gradient elution to afford the title compounds.

According to the analysis of related databases, 480-91-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wang, Yixuan; Wang, Huiqiang; Jiang, Xinbei; Jiang, Zhi; Guo, Tingting; Ji, Xingyue; Li, Yanping; Li, Yuhuan; Li, Zhuorong; Molecules; vol. 24; 5; (2019);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem