Category: indolines-derivatives

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. Recommanded Product: 19727-83-4

Step A 1-Methyl-6-nitroindoline Potassium bis(trimethylsilyl)amide (67 ml of a 0.5M toluene solution) was added slowly to a stirred solution of 6-nitroindoline (5.0 g) in anhydrous tetrahydrofuran (200 ml) at -78 C. under a nitrogen atmosphere. Iodomethane (2.09 ml) was added then the reaction mixture was allowed to warm to room temperature then stirred overnight. Methanol (5 ml) was added then the solution was evaporated to dryness. The residue was dissolved in diethyl ether (300 ml), washed with water, saturated brine then dried (magnesium sulphate) and evaporated to dryness. The crude product was purified by column chromatography on silica using 10% ethyl acetate/petroleum ether (60-80)?30% ethyl acetate/petroleum ether (60-80) and the product crystallized from diethyl ether/petroleum ether (60-80) to afford 0.9 g.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 19727-83-4, its application will become more common.

Reference:
Patent; Merck, Sharp & Dohme, Ltd.; US5696110; (1997); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

6941-75-9, name is 5-Bromoisoindoline-1,3-dione, 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: 6941-75-9

Synthesis of 5-bromo-3-hydroxy-3-(thiophen-3-yl) isoindolin-1-one (3) A solution of 1, 2-dibromoethane (20 ml, 230.35 mmol) in ether/benzene (270 ml/100 ml) was added to a stirred suspension of magnesium turning (8.64 g, 355.6 mmol) in ether (100 ml). The reaction was stirred at room temperature for 2 h. To this was added a solution of n-butyllithium (110 ml, 177.6 mmol) and 3-bromothiophene (2, 29 g, 177.6 mmol) in tetrahydrofuran (200 ml) (prepared at -78 C.) and the reaction was stirred at room temperature for 1 h. Then a solution of 4-bromophthalimide (1, 4 g, 17.7 mmol) in dichloromethane (50 ml) was added and the reaction was stirred at room temperature for 1 h. Progress of the reaction was monitored by TLC. After completion, the reaction mixture was quenched with sat. ammonium chloride and extracted with dichloromethane. The organic layer was separated, dried over sodium sulphate and concentrated under reduced pressure. The residue was purified on combiflash using 25% ethyl acetate in hexane to afford mixture of 5-bromo-3-hydroxy-3-(thiophen-3-yl) isoindolin-1-one (3) as a yellow solid. Yield: 0.97 g, crude; MS (ESI) m/z 307.95 [M-1]-.

The synthetic route of 6941-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; eFFECTOR Therapeutics, Inc.; Sprengeler, Paul A.; Reich, Siegfried H.; Ernst, Justin T.; Webber, Stephen E.; Shaghafi, Mike; Murphy, Douglas; Tran, Chinh; (131 pag.)US10112955; (2018); B2;,
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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, Recommanded Product: Isoindoline

To a stirred suspension of methyl 4-(bromomethyl)-3-methoxybenzoate (0.53 g, 2.04 mmol, 1 eq.) and potassium carbonate (0.56 g, 4 mmol, 2 eq.) in N,N-dimethylformamide (5 mL) was added isoindoline (280 mu^, 2.45 mmol, 1.2 eq.). The resulting mixture was then stirred at room temperature for 17 hours. The solvent was removed in vacuo and the crude product was partitioned between water and dichloromethane, the layers were separated and the aqueous phase extracted with dichloromethane. The combined extracts were dried with magnesium sulfate and evaporated in vacuo. The residue was purified by silica gel column chromatography using a 10 – 100 % ethyl acetate in wo-hexane gradient to afford methyl 4- (isoindolin-2-ylmethyl)-3-methoxybenzoate as a red liquid (0.417 g, 70 % yield). NMR (400 MHz, CDC13) 7.66 (1H, d, J=7.8 Hz), 7.55-7.53 (2H, m), 7.18 (4H, s), 4.0-3.98 (6H, m), 3.92-3.91 (6H, m).

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; GENKYOTEX SA; MACHIN, Peter; SHARPE, Andrew; LOCK, Christopher James; CHAMBERS, Mark S; HODGES, Alastair; ALLEN, Vivienne; ELLARD, John M; (189 pag.)WO2016/98005; (2016); A1;,
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Indoline | C8H9N – PubChem

Electric Literature of 5332-26-3, These common heterocyclic compound, 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, 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: The vacuum dried intermediate 3 (0.002 mol) was then reacted with mono- and di-substituted benzoic acids (0.003 mol) separately in presence of anhydrous potassium carbonate (0.003 mol) in DMF (10 mL). The reaction mixture was stirred at room temperature for about 2 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was poured into ice-cold water and allowed stir for 10 min. The solid obtained was filtered and washed successively with distilled water and recrystallized from ethanol to obtain4(a-n).

Statistics shows that 2-(Bromomethyl)isoindoline-1,3-dione is playing an increasingly important role. we look forward to future research findings about 5332-26-3.

Reference:
Article; Kumar, C.S. Chidan; Loh, Wan-Sin; Chandraju, Siddegowda; Win, Yip-Foo; Tan, Weng Kang; Quah, Ching Kheng; Fun, Hoong-Kun; PLoS ONE; vol. 10; 3; (2015);,
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. 1914-02-9, name is 3,3-Dimethylindoline, A new synthetic method of this compound is introduced below., category: indolines-derivatives

A mixture of 3,3-dimethylindoline (2.1 g, 14.26 mmol) and 2-bromoethanamine hydrobromide (3.215 g,15.69 mmol) was heated at 122 C for 15 h. The mixture was dissolved in 2M HCl and purified bypreparative HPLC to give the title compound (1.9 g). LCMS m/z = 191.4 [M+H]+; 1H NMR (400 MHz,CD3OD) delta ppm 1.31 (s, 6H), 3.14 (s, 2H), 3.19 (t, 2H, J = 6.1Hz), 3.33 (t, 2H, J = 6.1 Hz), 6.60 (d, 1H, J = 7.9Hz), 6.70-6.76 (m, 1H), 7.01-7.09 (m, 2H).

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; Dang, Huong; Feichtinger, Konrad; Frazer, John; Grottick, Andrew J.; Kasem, Michelle; Le, Minh; Lehman, Juerg; Morgan, Michael E.; Ren, Albert; Sage, Carleton R.; Schrader, Thomas O.; Semple, Graeme; Unett, David J.; Whelan, Kevin T.; Wong, Amy; Zhu, Xiuwen; Bioorganic and medicinal chemistry letters; (2020);,
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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., Formula: C11H9NO3

A mixture of 2,3-dihydro-1H-inden-2-amine (5.0 g, 24.61 mmol) and (R)-2-(oxiran-2-ylmethyl)isoindoline-1,3-dione (4.91 g, 36.91 mmol) in EtOH (100 mL) was heated at reflux overnight. After cooling to room temperature, triethylamine (9.94 g, 98.44 mmol) and (Boc)2O(10.74 g, 49.22 mmol) were added and the reaction mixture was stirred at room temperature overnight. The mixture was concentrated and purified by column (EtOAc / petroleum ether = 1/4, v/v) to give the title compound (5.4 g, 50%) as an oil.

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; CTxT PTY LIMITED; STUPPLE, Paul Anthony; (66 pag.)WO2017/153521; (2017); A1;,
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Indoline | C8H9N – PubChem

Application of 3339-73-9,Some common heterocyclic compound, 3339-73-9, name is 3-(1,3-Dioxoisoindolin-2-yl)propanoic acid, molecular formula is C11H9NO4, 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 4 (0.3 g, 1.37 mmol) in CH2Cl2 (10 mL) was added thionyl chloride (0.12 mL, 1.6 mmol). The resulting mixture was stirred at reflux for 5 h. After cooling to rt, the solvent and excess thionyl chloride were removed by evaporation to give a white solid (0.22 g) in 67% yield; 1H NMR (400 MHz, CDCl3) delta 7.87 (m, 2H), 7.74 (m, 2H), 4.04 (m, 2H), 3.35 (m, 2H); 13C NMR (100 MHz, CDCl3) delta 168.0, 166.2, 134.2, 123.5, 33.9, 33.0; mp 148-150?C. The product was used in the next step without further purification.

The synthetic route of 3339-73-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Peng; Jorgensen, Trine Nygaard; Loland, Claus J.; Newman, Amy Hauck; Bioorganic and Medicinal Chemistry Letters; vol. 23; 1; (2013); p. 323 – 326;,
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Indoline | C8H9N – PubChem

Related Products of 20876-36-2, These common heterocyclic compound, 20876-36-2, name is 5-Aminoindolin-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.

To a solution of 5-amino oxindole (2 g, 13.5 mmol) in 80 ml of water/dioxane 3:1 was added sodium hydroxide 1N until obtaining pH 10 and then di-t-Butyl pyrocarbonate (3.5 g, 16.2 mmol). The reaction was stirred for 3 h maintaining pH 10. After extraction with 3*10 ml of ethyl acetate, the extracted were dried over sodium sulphate and evaporated obtaining 2.4 g of 5-t-Butoxycarbonylamino oxindole (71percent yield). 1 H-NMR (400 MHz, DMSO, T=45¡ã C.) 1.49 (s, 9H); 3.87 (s, 3H); 6.72 (d, J=8.4 Hz, 1H); 6.86 (dd, J=2.2 Hz, J=8.8 Hz, 1H); 7.12 (dd, J=1.8 Hz, J=8.4 Hz, 1H); 7.40 (d, J=8.8 Hz, 1H); 7.54 (d, J=2.2 Hz, 1H); 7.78 (d, J=1.8 Hz, 1H); 7.92 (s, 1H); 8.87 (bs, 1H); 9.38 (s, 1H); 10.25 (s, 1H); 11.8 (bs, 1H). FD-MS: 248 (100, [M]+); 191 (18, M-C4 H9!+); 147 (5, M-(CH3)3[COCO]+)

The synthetic route of 20876-36-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pharmacia & Upjohn S.p.A.; US5849710; (1998); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 2058-74-4, 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 2058-74-4 as follows.

General procedure: To a stirred mixture of 1-benzyl-1H-indole-2,3-dione (1a, 0.25 g,1.05 mmol), CuI (0.01 g, 0.05 mmol, 0.05 equiv), and phenylacetylene (2a, 0.11 g, 1.11 mmol, 1.05 equiv) in anhyd toluene (2 mL), DBU (0.032 g, 0.21 mmol, 0.2 equiv) was added at 25 C under a N2 atmosphere. Stirring was continued at this temperature until the starting material was completely consumed (TLC monitoring). After completion, the mixture was quenched with sat. aq NH4Cl (2mL) and extracted with EtOAc (2 ¡Á 5 mL). The combined organic layers were dried (anhyd Na2SO4) and evaporated under reduced pressure to dryness. The crude product thus obtained was purified by column chromatography (activated silica gel, 60-120 mesh, hexane-EtOAc) to afford pure 3aa as a white solid; yield: 0.35 g (97%); mp 177-179 C.

According to the analysis of related databases, 2058-74-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Chouhan, Mangilal; Senwar, Kishna Ram; Kumar, Kapil; Sharma, Ratnesh; Nair, Vipin A.; Synthesis; vol. 46; 2; (2014); p. 195 – 202;,
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 552330-86-6 as follows. COA of Formula: C8H6BrNO

General procedure: 5-Bromo-2-methylisoindolin-1-one (520 mg, 2.30 mmol) and thiophene-2-boronic acid (442mg, 3.45 mmol) were dissolved in a mixure of toluene (12 mL) and EtOH (6 mL). A solutionof 2 M Na2CO3 (3 mL) and Pd(dppf)Cl2 (94 mg, 0.12 mmol) were added and the entiremixture heated at reflux under N2 for 2 h. Additional thiophene-2-boronic acid (294 mg, 2.30mmol) was added and reflux continued under N2 overnight. Upon cooling, the mixture wasdiluted with water (100 mL) and extracted with CH2Cl2 (6×50 mL). The combined organicfractions were dried (Na2SO4), filtered, and the solvent removed under reduced pressure togive a crude solid which was purified by flash column chromatography on silica gel (EtOAcas eluant). The title compound was isolated as a light-brown solid (510 mg, 97%).

According to the analysis of related databases, 552330-86-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Spicer, Julie A.; Miller, Christian K.; O’Connor, Patrick D.; Jose, Jiney; Huttunen, Kristiina M.; Jaiswal, Jagdish K.; Denny, William A.; Akhlaghi, Hedieh; Browne, Kylie A.; Trapani, Joseph A.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 4; (2017); p. 1050 – 1054;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem