Category: 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. name: Isoindolin-1-one

A mixture of isoindolin-1-one (150 mg, 1.13 mmol), 1D (300 mg, 1.13 mmol), Pd2(dba)3 (31 mg, 0.034 mmol), Xantphos (20 mg, 0.034 mmol) and Cs2CO3 (443 mg, 1.36 mmol) in dioxane (25 mE) was heated to 100 C. for 16 hours under a nitrogen atmosphere. The reaction mixture was allowed to cool to room temperature, filtered and the resulting filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (1-5% MeOH in DCM) to afford compound 1 (270 mg, 75% yield) as an off-white solid: ?H NMR (400 MHz DMSO-d5) oe 8.71 (s, 1H), 8.64 (d, J=8.4 Hz, 1H), 8.07 (t, J=8 Hz, 1H), 7.88-7.83 (m, 2H), 7.72 (d, J=8.4 Hz, 2H), 7.59-7.53 (m, 1H), 5.18 (s, 2H), 4.12-4.07 (m, 1H), 1.14-1.09 (m, 2H), 1.0-0.95 (m, 2H); ESI mlz 318.1[M+1].

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:
Patent; Seal Rock Therapeutics, Inc.; BROWN, Samuel David; US2018/291002; (2018); A1;,
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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. 480-91-1, name is Isoindolin-1-one, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 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.

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

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: 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.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 480-91-1, and friends who are interested can also refer to it.

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

480-91-1, A common compound: 480-91-1, name is Isoindolin-1-one, belongs to indolines-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

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.

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; 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

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.

A mixture of 84B (225 mg, 1.0 mmol), 197 isoindolin-1-one (133.1 mg, 1.0 mmol), 51 Pd2(dba)3 (28 mg, 0.03 mmol), Xantphos (29 mg, 0.05 mmol) and 50 Cs2CO3 (391 mg, 1.2 mmol) in 52 dioxane (45 mL) was heated to 100 C. overnight. After cooling to room temperature, the reaction mixture was filtered. The filtrate was concentrated under vacuum and the residue was purified by column chromatography on silica gel (1%-30% 32 EtOAc in 60 pet. ether) to provide 233 compound 84 (170 mg, 61% yield) as a white solid: 1H NMR (400 MHz, CDCl3) delta 8.72 (dd, J=7.6 Hz, 6.4 Hz, 1H), 8.57 (d, J=1.2 Hz, 1H), 8.01-7.94 (m, 3H), 7.86 (d, J=0.8 Hz, 1H), 7.69-7.65 (m, 1H), 7.59-7.52 (m, 2H), 5.14 (s, 2H) ; ESI m/z 278.0 [M+H]+ .

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; Seal Rock Therapeutics, Inc.; BROWN, Samuel David; US2018/291002; (2018); 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. 480-91-1, name is Isoindolin-1-one, A new synthetic method of this compound is introduced below., 480-91-1

Phthalimidine (1.60g, 12.0mmol) was dissolved in THF (80mL). Triethylamine (1.34g, 13.2mmol) was added dropwise and the mixture was stirred for 5min at ambient temperature. Chlorodiphenylphosphine (2.65g, 12.0mmol) was added and the mixture was stirred for three days, whereupon the white precipitate was filtered and washed with THF (2¡Á3mL). The combined filtrate and washings were evaporated to dryness (condensation of volatiles into a cold trap under reduced pressure) and the residue was recrystallized from THF (27.5mL). The white crystalline product was suitable for single-crystal X-ray diffraction. The supernatant was decanted, the white solid was washed with Et2O (3mL) and dried in vacuo to yield 2.33g (7.34mmol, 61%) of 1b. (0014) Anal. Calc. for C20H16NOP (MW: 317.3), requires: C, 75.70; H, 5.08; N, 4.41. Found: C, 75.83; H, 5.18; N, 4.43%. 1H NMR (CDCl3, delta ppm): 4.18 (s, -CH2-, 2H), 7.33 (d, J=7.54Hz, aryl, 1H), 7.38-7.50 (br. m, aryl, 11H), 7.54 (dt, J=7.45Hz, J=1.10Hz, aryl, 1H), 7.94 (d, J=7.54Hz, aryl, 1H). 13C{1H} NMR (CDCl3, delta ppm): 49.2 (d, J=7.1Hz), 123.0 (s), 124.6 (s), 128.2 (s), 128.7 (d, J=6.2Hz), 129.6 (s), 132.1 (s), 132.2 (s), 132.5 (d, J=21.1Hz), 135.7 (d, J=14.4Hz), 143.8 (s), 173.3 (d, J=17.3Hz), 31P{1H} NMR (CDCl3, delta ppm): 29.7 (s).

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; Gericke, Robert; Wagler, Joerg; Polyhedron; vol. 120; (2016); p. 134 – 141;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

480-91-1, A common heterocyclic compound, 480-91-1, name is Isoindolin-1-one, molecular formula is C8H7NO, 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 solution of isoindolin-1-one (1.00 g, 7.51 mmol) in freshly-distilled THF (25 mL) was added slowly to a suspension of sodium hydride (450 mg, 11.26 mmol, freshly washed with hexane) in THF (25 mL) under N2 at 0 C and stirring was continued (30 min). To the reaction mixture was slowly added ethyl bromoacetate (1.24 mL, 11.26 mmol) and the resulting reaction mixture was allowed to stir at room temperature (16 h). The reaction mixture was quenched with methanol and concentrated. The obtained crude residue was further purified by gravity column chromatography (hexane/ethyl acetate, 2:1) provided pure 1 as an off-white solid (1.39 g, 78%); mp = 77-79C (Lit. mp = 78-80 C)1. 1H NMR (400 MHz, CDCl3) delta 7.87-7.85 (d, J = 7.6 Hz, 1H), 7.57-7.53 (m, 1H), 7.48-7.44 (m, 2H), 4.518 (s, 2H), 4.39 (s, 2H), 4.22 (q, J = 6.8 Hz, 2H), 1.28 (t, J = 6.8 Hz, 3H) ppm. The spectroscopic data was consistent with that previously reported.1

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

Reference:
Article; Patil, Pravin C.; Luzzio, Frederick A.; Ronnebaum, Jarrid M.; Tetrahedron Letters; vol. 58; 38; (2017); p. 3730 – 3733;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

480-91-1, A common heterocyclic compound, 480-91-1, name is Isoindolin-1-one, molecular formula is C8H7NO, 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.

[0198] 2,3-Dihydroisoindol-l-one (350 mg, 2.63 mmol), 1,4-bis-bromomethylbenzene (3.78 g, 14.3 mmol), CS2CO3 (3.60 g, 11.1 mmol), in acetonitrile (20 mL), was stirred together at room temperature for 5 hours and 80 C for 20 minutes. The reaction was partitioned between ethyl acetate and water and the organic layer was washed with brine and dried over anhydrous Na2S04. The solvent was removed under reduced pressure and the product was purified by column chromatography (30% EtOAc/Hexanes) to afford a white solid (410 mg, 49%). .H NMR (300 MHz, CDC13): 6 7.92 (d, 1H), 7.49- 7.55 (m, 2H), 7.37-7.42 (m, 3H), 7.28-7.31 (m, 2H), 4.82 (s, 2.03), 4.49 (s, 2H), 4.31 (s, 2H).

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

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

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. 480-91-1

To a solution of 2,3-dihydroisoindole-1-one (5 g, 38 mmol) in concentrated sulfuric acid (100 ml) at 0 C., KNO3 was added portionwise whilst maintaining the temperature at 0 C. The reaction was gradually allowed to warm to room temperature and was stirred overnight. The reaction mixture was poured into ice and the resulting precipitate was filtered off and dried to give title compound as a yellow solid (4.7 g, 70%). 1H NMR (360 MHz, d6 DMSO) ? 8.96 (1H, s), 8.45 (1H, dd, J=8.3 Hz, 2.2 Hz), 8.34 (1H, d, J=2 Hz), 7.87 (1H, d, J=8.3 Hz), 4.54 (2H, s). m/z (ES+) 179 (M+).

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; Boase, Amanda Louise; Ladduwahetty, Tamara; MacLeod, Angus Murray; Merchant, Kevin John; US2004/58970; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

480-91-1, A common heterocyclic compound, 480-91-1, name is Isoindolin-1-one, molecular formula is C8H7NO, 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: Method A: To a stirred suspension of the appropriate nitrogen derivative II (0.16 mmol) and chlorophosphine gold(l) compound III (0.16 mmol) in MeOH (2 mL) was added dropwise NaOMe (0.5 M in MeOH , 0.18 mmol). The reaction was stirred at rt for 16 h before concentrating in vacuo to give a solid residue which was suspended in DCM (2 mL) and filtered. The filtrate was concentrated in vacuo giving an oily residue which after trituration with Et.20 (x 3) and drying under high vacuum for 16 h, provided the title compound I. Method E: As Method A except the reaction mixture was heated at 50 C for 18 h.

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

Reference:
Patent; AUSPHERIX LIMITED; HOLMES, Ian; NAYLOR, Alan; ALBER, Dagmar; POWELL, Jonathan Raymond; MAJOR, Meriel Ruth; NEGOITA-GIRAS, Gabriel; ALLEN, Daniel Rees; GUETZOYAN, Lucie Juliette; KING, Nigel Paul; CHAPMAN, Nicholas Andrew; (155 pag.)WO2017/93545; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem