Category: indolines-derivatives

Some common heterocyclic compound, 19155-24-9, name is 3,3-Dimethylindolin-2-one, molecular formula is C10H11NO, 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. Application In Synthesis of 3,3-Dimethylindolin-2-one

To a solution of 3,3-dimethylindolin-2-one (1.5 g, 9.31 mmol) in THF (90 mL) was added borane-THF complex (37.3 mL, 37.22 mmol) at 0 C. The reaction was refluxed at 87 C overnight, then cooled to rt, and quenched with MeOH (10 mL). The mixture was reflux at 85 C for 2 h, and then concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (v/v) = 20/1) to give the title compound as yellow oil (0.87 g, 63.5%). MS (ESI, pos. ion) m/z: 148 [M + H]+; NMR (CDCI3) delta (ppm): 7.11-7.07 (m, 2H), 6.80 (t, 1H), 6.69 (d, 1H), 3.57 (s, 1H), 3.35 (s, 2H), 1.37 (s, 6H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 19155-24-9, its application will become more common.

Reference:
Patent; CALITOR SCIENCES, LLC; SUNSHINE LAKE PHARMA CO., LTD; XI, Ning; WANG, Ruyong; WANG, Liang; WO2014/89324; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 611-09-6, name is 5-Nitroindoline-2,3-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 611-09-6, Recommanded Product: 611-09-6

General procedure: The preparation was divided into two steps. Firstly, substituent indoline-2,3-dione (1 equiv) was dissolved in ethanol (10 mL), hydrazine hydrate (2 mL) was added. The reaction mixture was refluxed with magnetic stirring for 3 h and cooled to 0 C, then sodium hydroxide (3 equiv) was added, refluxed for 0.5 h and cooled to room temperature, then 150 mL water was added. The mixture was acidified by adding 2 N hydrochloric acid to pH 2, and extracted twice with dichloromethane. The organic filtrate was washed twice with brine, dried (Na2SO4), and then concentrated to give corresponding indolin-2-one by high-vacuum drying. Secondly, a mixture of the corresponding indolin-2-one (1 equiv) and furan-2-carbaldehyde (1 equiv) in ethanol was added two drops of piperidine and refluxed with magnetic stirring for 5 h. After the mixture cooled, the precipitate was filtered, washed with cold ethanol, dried, and recrystallized from methanol to afford the terminal product.

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, 5-Nitroindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zhong, Ye; Xue, Mengzhu; Zhao, Xue; Yuan, Jun; Liu, Xiaofeng; Huang, Jin; Zhao, Zhenjiang; Li, Honglin; Xu, Yufang; Bioorganic and Medicinal Chemistry; vol. 21; 7; (2013); p. 1724 – 1734;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

5332-26-3, name is 2-(Bromomethyl)isoindoline-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. Recommanded Product: 5332-26-3

A solution of n-butyllithium in THF (1.8 ml, 2.5 M, 4.5mmol) was added in to a cooled mixture of HMDS (608 mg, 4.56 mmol) in THF (20 ml) dropwise over 20 min with stirring. The mixture was stirred for 30 min before benzyl 2-(4- ((cyclopropylmethyl)sulfonyl)phenyl)acetate (1.3 g, 3.8 mmol) in THF (5 ml) was added through a syringe dropwise over 10 min. Stirred for another 30 min at -78 followed by the addition of 2-(bromomethyl)isoindoline-1,3-dione (912 mg, 3.8 mmol) in THF (5 ml) was added through a syringe over 10 min. The mixture was stirred at -78 and allowed to reach to room temperature overnight. The mixture was treated with methanol carefully and the solvents were evaporated. The product was purified by flash chromatography to affod the product as a White solid 1.4 g (74% yield). MS (+) ES: 504 (M+H)+.

The synthetic route of 5332-26-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ETERNITY BIOSCIENCE INC.; YAN, Yinfa; ZHANG, Minsheng; LIU, Dong; ZHANG, Fengqi; LIU, Suxing; ZHANG, Rumin; HE, Feng; TAO, Weikang; (211 pag.)WO2019/213470; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 129487-92-9, name is tert-Butyl 5-aminoindoline-1-carboxylate, molecular formula is C13H18N2O2, 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. Computed Properties of C13H18N2O2

To a solution of 2-bromo-3-((4-fluorophenyl)ethynyl)pyridine (intermediate 42, 340 mg, 1.23inmol) in anhydrous toluene (15 rnL) was added Pd2(dba)3 (113 mg, 0.123 mmol), XPhos (117 rng,0.246 mmoi) and potassium tert-butoxide (414 mg, 3.69 mrnol) under N2. After 10 mm, tert-butyl5-aminoindoline- I -carboxylate (Intermediate 12, 519 mg, 1.75 mmol) was added and the mixturewas stirred at 20 C for 10 mm, Then, the mixture was heated at 100 C for 3hr, EtOAc and waterwere added. The organic phase was separated and dried (Mg504), filtered and concentrated.Purification IFCC. Si02 0:100 to 30:70, EtOAc/heptane) afforded the title compound (330 mg,62%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 129487-92-9, its application will become more common.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BERRY, Cynthia G.B.; CHEN, Gang; JOURDAN, Fabrice Loic; LEBOLD, Terry Patrick; LIN, David Wei; PENA PINON, Miguel Angel; RAVULA, Suchitra; SAVALL, Bradley M.; SWANSON, Devin M.; WU, Dongpei; ZHANG, Wei; AMERIKS, Michael K.; (407 pag.)WO2016/176460; (2016); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 16800-68-3, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 16800-68-3, name is 1-Acetylindolin-3-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of 1a (35 mg, 0.2 mmol) and 2a (52.4 mg,0.4 mmol) in DCE (3 mL) was added iodine (10 mg, 0.04 mmol). The reaction mixture was heated at 80 C for 24 h, then cooled to room temperature and quenched with saturated sodium thiosulfate. The mixture was extracted with CH2Cl2, the combined organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel to afford title compound.

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, 1-Acetylindolin-3-one, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Guo, Jing; Weng, Jiang; Huang, Gong-Bin; Huang, Lin-Jie; Chan, Albert S.C.; Lu, Gui; Tetrahedron Letters; vol. 57; 49; (2016); p. 5493 – 5496;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 56341-37-8, name is 6-Chlorooxindole, 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 56341-37-8, Recommanded Product: 6-Chlorooxindole

To the mixture of 6-chloro-2-oxindole (16.2 g, 92 mmol) (Crescent) and 3-chloro-benzaldehyde (12.9 g, 92 mmol) (Aldrich) in methanol (109 mL) was added pyrrolidine (6.55 g, 92 mmol) (Aldrich) dropwise. The mixture was then heated at 70 C. for 3 h. After cooled to 4 C., the mixture was filtered and resulting precipitate was collected, dried to give a mixture of E/Z-6-chloro-3-(3-chloro-benzylidene)-1,3-dihydro-indol-2-one as a bright yellow solid (Yield 25.2 g, 95%).

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; Bartkovitz, David Joseph; Chu, Xin-Jie; Ding, Qingjie; Graves, Bradford James; Jiang, Nan; Zhang, Jing; Zhang, Zhuming; US2011/130398; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 2436-29-5,Some common heterocyclic compound, 2436-29-5, name is 3-(1,3-Dioxoisoindolin-2-yl)propanal, molecular formula is C11H9NO3, 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 4b (1.00 g, 3.63 mmol) and 7b (1.11 g, 5.45 mmol) in THF (35 mL) was added NH4OAc (2.80 g, 36.3 mmol) in MeOH (35 mL). The reaction mixture was stirred at reflux temperature for 2 h and concentrated. The residue was diluted in CHCl3 and washed with a saturated aqueous solution of Na2CO3. The organic layer was dried over MgSO4 and concentrated. The crude product was purified by column chromatography on silica gel eluting with 0-5% MeOH/CHCl3 to afford 2-{2-[5-(1,3-benzodioxol-5-yl)-4-(4-methyl-1,3-thiazol-2-yl)-1H-imidazol-2-yl]ethyl}-1H-isoindole-1,3(2H)-dione as a yellow amorphous (1.14 g, 69%): 1H NMR (200 MHz, CDCl3, delta): 2.42 (d, J = 0.7 Hz, 3H), 3.22 (t, J = 6.8 Hz, 2H), 4.15 (t, J = 6.8 Hz, 2H), 6.00 (s, 2H), 6.69 (s, 1H), 6.85 (d, J = 8.1 Hz, 1H), 7.09 – 7.35 (m, 2H), 7.69 – 7.87 (m, 4 H); MS (ESI) m/z 459 [M+H]+, 35%, 481 [M+Na]+, 100%, 457 [M-H]-, 100%. To a suspension of 2-{2-[5-(1,3-benzodioxol-5-yl)-4-(4-methyl-1,3-thiazol-2-yl)-1H-imidazol-2-yl]ethyl}-1H-isoindole-1,3(2H)-dione (1.12 g, 2.43 mmol) in EtOH (60 mL) was added hydrazine monohydrate (1.18 mL, 24.3 mmol). The reaction mixture was stirred at reflux temperature for 8 h. The mixture was cooled to room temperature and filtered. The filtrate was concentrated and the crude product was purified by column chromatography on NH-silica gel eluting with 2-7% MeOH/CHCl3 to afford 8b as a pale yellow amorphous (567 mg, 71%): 1H NMR (300 MHz, CDCl3, delta): 2.44 (d, J = 0.9 Hz, 3 H), 2.91 (t, J = 5.9 Hz, 2 H), 3.18 (t, J = 5.9 Hz, 2 H), 6.00 (s, 2 H), 6.70 (d, J = 0.9 Hz, 1 H), 6.86 (d, J = 8.1 Hz, 1 H), 7.24 (dd J = 8.1, 1.7 Hz, 1 H), 7.36 (d, J = 1.7 Hz, 1 H); MS (ESI) m/z 329 [M+H]+, 90%, 351 [M+Na]+, 100%, 327 [M-H]-, 100%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-(1,3-Dioxoisoindolin-2-yl)propanal, its application will become more common.

Reference:
Article; Amada, Hideaki; Sekiguchi, Yoshinori; Ono, Naoya; Matsunaga, Yuko; Koami, Takeshi; Asanuma, Hajime; Shiozawa, Fumiyasu; Endo, Mayumi; Ikeda, Akiko; Aoki, Mari; Fujimoto, Natsuko; Wada, Reiko; Sato, Masakazu; Bioorganic and Medicinal Chemistry Letters; vol. 22; 5; (2012); p. 2024 – 2029;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 17702-83-9, name is 2-(8-Bromooctyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. category: indolines-derivatives

General procedure: Procedure M2. A mixture of the appropriate 2-(bromoalkyl)-isoindoline-1,3-dione (1 equiv)with 1,2,3,4-tetrahydoisoquinoline (1 equiv) in the presence of K2CO3 (2.5-3 equiv) was stirred inacetonitrile under reflux for 20 h. Subsequently, the solvent was evaporated under vacuum, producinga residue which was further dissolved in 40 mL of sodium bicarbonate and extracted with ethyl acetate(3 x 30 mL). The organic layer was acidified 2 M HCl and extracted with distilled water (3 x 30 mL).Then, the combined aqueous extracts were alkalized using 4M NaOH, extracted with DCM and driedwith anhydrous Na2SO4. The solvent was then evaporated and the residue was purified by silica gelcolumn chromatography (S4) yielding a yellow oil. The final product was obtained in the form ofhydrochloride salt. The following compounds were obtained.

The synthetic route of 17702-83-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Hebda, Michalina; Bajda, Marek; Wieckowska, Anna; Szal?aj, Natalia; Pasieka, Anna; Panek, Dawid; Gody?, Justyna; Wichur, Tomasz; Knez, Damijan; Gobec, Stanislav; Malawska, Barbara; Molecules; vol. 21; 4; (2016);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 667463-64-1, name is 6-Bromo-1-methylindoline-2,3-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 667463-64-1, SDS of cas: 667463-64-1

General procedure: Unless indicated otherwise, a solution of 2-aminobenzamide 1 (0.1 mmol), isatin 2 (0.1 mmol), the catalyst 4e (0.02 mmol), and 5 A molecular sieves (30 mg) in 1,2-dichloroethane (2 mL) was stirred at 70 C for 12 h. Next, the reaction mixture was diluted with acetone, which was then filtered to remove molecular sieves and the solid powder was washed with acetone. The resultant solution was condensed by evaporation under reduced pressure, which was further purified through preparative thin layer chromatography on silica gel to yield pure products 3.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Bromo-1-methylindoline-2,3-dione, and friends who are interested can also refer to it.

Reference:
Article; Jiang, Yan; Liu, Yan; Tu, Shu-Jiang; Shi, Feng; Tetrahedron Asymmetry; vol. 24; 20; (2013); p. 1286 – 1296;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 317-20-4,Some common heterocyclic compound, 317-20-4, name is 7-Fluoroisatin, molecular formula is C8H4FNO2, 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 7-fluoroindoline-2,3-dione (500 mg, 3.03 mmol) in DMF (5 mL) were successively added K2C03 (502 mg, 3.63 mmol) and methyl iodide (0.199 mL, 3.18 mmol). The resulting mixture was stirred at RT for 1 hr. The mixture was quenched with water, diluted with EtOAc and saturated aqueous NaHC03 solution and both phases were separated. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried over anhydrous MgS04, filtered and concentrated under reduced pressure to afford the title product (497 mg, 2.219 mmol, 73.3% yield) as yellow solid. Rt = 0.69 min (UPLC-MS); ESI-MS = 179.9 [M+1]+ (UPLC-MS).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7-Fluoroisatin, its application will become more common.

Reference:
Patent; NOVARTIS AG; ARISTA, Luca; CHAMOIN, Sylvie; D’ALESSANDRO, Pier Luca; LINDVALL, Mika; LIZOS, Dimitrios; STIEFL, Nikolaus Johannes; TEIXEIRA-FOUCHARD, Sylvie; ULLRICH, Thomas; WEILER, Sven; (151 pag.)WO2019/102256; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem