Indolines-derivatives

Reference of 6941-75-9,Some common heterocyclic compound, 6941-75-9, name is 5-Bromoisoindoline-1,3-dione, molecular formula is C8H4BrNO2, 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 fuming nitric acid (9.2 mL, 0.22 mol, 1.0 eq) pre-cooled at 0 C. was added drop wise concentrated sulfuric acid (21 mL, 0.40 mol, 1.8 eq) followed by portion-wise addition of intermediate I-55 (10 g, 44 mmol, 2.0 eq) and the resulting suspension was warmed to room temperature over 1 hour and stirred for a additional 24 hours at room temperature. The crude reaction mixture was poured onto a mixture of ice and water and the solids were collected by filtration and dried in vacuo to give intermediate I-56 (11.8 g, 98%). MS (ESI): m/z 272 (M+H+).

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

Reference:
Patent; Chytil, Milan; Engel, Sharon R.; Fang, Qun Kevin; Spear, Kerry L.; US2010/204214; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 3484-35-3,Some common heterocyclic compound, 3484-35-3, name is 5-Methylindolin-2-one, molecular formula is C9H9NO, 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: To a solution of 3-substituted-5-benzylidene-2-thioxo-4-thiazolidinone (3a-3h, 8a-8f) (0.003 mol) in 1,4-dioxane (15 ml) was added HC(OEt)3 (2 ml) and BF3·Et2O (2 ml). The reaction mixture was heated to 80 C and stirring was continued at the same temperature for 4 h. The resulting 2-ethylthio-3-substituted-5-benzylidene-4-thiazolium fluoroborate (4a-4h, 9a-9f) was precipitated, filtered off, and dried without any additional purification, as starting material for the following reactions. To a mixture of thiazolium fluoroborate (4a-4h, 9a-9f) (0.003 mol) and indolin-2-one (11a-11f) (0.003 mol) in acetonitrile (15 ml) was added triethylamine (0.91 g, 0.009 mol) dropwise at 25 C, and the mixture was stirred for 4 h at the same temperature. The orange precipitate was collected and washed with ethyl acetate (8 ml). The crude product thus obtained was recrystallized from methanol or acetone to give compound (5a-5s, 10a-10s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Methylindolin-2-one, its application will become more common.

Reference:
Article; Wang, Shuobing; Zhao, Yanfang; Zhang, Guogang; Lv, Yingxiang; Zhang, Ning; Gong, Ping; European Journal of Medicinal Chemistry; vol. 46; 8; (2011); p. 3509 – 3518;,
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Related Products of 141452-01-9,Some common heterocyclic compound, 141452-01-9, name is Methyl indoline-5-carboxylate, molecular formula is C10H11NO2, 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.

(R)- l-(4-cyclopentyl- 1 ,3-dimethyl-2-oxo- 1 ,2,3,4-tetrahydropyrido [2,3-6] pyrazin-6- yl)indoline-5-carboxylic acid (i?)-6-chloro-4-cyclopentyl-l ,3-dimethyl-3,4-dihydropyrido[2,3-]pyrazin-2(lH)- one (42.0 mg, 0.15 mmol, 1 eq), methyl indoline-5-carboxylate (31.9 mg, 0.180 mmol, 1.2 eq), Pd2dba3 (6.9 mg, 0.0075 mmol, 5 mol%), XPhos (10.7 mg, 0.0225 mmol, 15 mol%) and K2C03 (82.9 mg, 0.60 mmol, 4 eq) were dissolved in tBuOH (1.5 mL, 0.1 M) and heated to 100 C for 20 hours. The mixture was filtered through celite, washed with DCM/EtOAc/MeOH and condensed. Purification by column chromatography (ISCO, 4 g silica column, 0-10%MeOH/DCM, 15 minute gradient) gave a mixture of the desired methyl ester and the (inconsequential) ethyl ester, which was used without further purification (65.56 mg). LCMS 40.48 (M+H), 435.47 (ethyl ester M+H). The resulting material was dissolved in THF (0.78 mL) and water (0.39 mL). LiOH (5.6 mg) was added and the mixture was stirred at room temperature. Due to poor solubility and sluggish conversion, an additional 5.6 mg LiOH, 0.39 mL water and 0.39 mL MeOH were added. After 2 days, the mixture was diluted with MeOH and purified by preparative HPLC to give a dark brown oil (33.84 mg, 0.08325 mmol, 53% over 2 steps. 1H NMR (400 MHz, Methanol-^) delta 8.11 (d, J= 8.6 Hz, 1H), 7.82 (dd, J= 8.6, 1.7 Hz, 1H), 7.76 (s, 1H), 7.23 – 7.16 (m, 1H), 6.24 (d, J= 8.5 Hz, 1H), 4.61 – 4.52 (m, 1H), 4.28 (q, J = 6.8 Hz, 1H), 4.06 (t, J= 8.8 Hz, 2H), 3.31 (s, 3H), 3.19 (t, J= 8.7 Hz, 2H), 2.09 (ddd, J = 17.1, 12.9, 8.7 Hz, 2H), 1.86 – 1.61 (m, 6H), 1.18 (d, J= 6.8 Hz, 3H). 13C NMR (100 MHz, cd3od) delta 169.88, 168.00, 150.16, 146.41, 132.06, 131.00, 126.64, 123.78, 121.72, 117.96, 112.26, 98.72, 58.11, 54.52, 50.70, 30.98, 30.72, 29.27, 27.49, 24.04, 23.33, 17.03. LCMS 407.48 (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 Methyl indoline-5-carboxylate, its application will become more common.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; BRADNER, James, E.; GRAY, Nathanael; QI, Jun; MCKEOWN, Michael, R.; BUCKLEY, Dennis; WO2015/117055; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 883-44-3, name is 2-(3-Hydroxypropyl)isoindoline-1,3-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 883-44-3, Computed Properties of C11H11NO3

Step 2. Preparation of 3-(l,3-dioxoisoindolin-2-yl)propanal A mixture of 2-(3-hydroxypropyl)isoindoline-l,3-dione (2.0 g, 8.76 mmol) and IBX (8.2 g, 29.27 mmol) in 60 mL EA was refluxed for 2 h. The mixture was filtered and filtrate was concentrated to afford 3-(l,3-dioxoisoindolin-2-yl)propanal (2.0 g , yield: 100%) as white solid. NMR (500 MHz, CDC13): delta 9.82 (s, 2H), 7.84-7.86 (m, 2H), 7.72-7.74 (m, 2H), 4.04 (t, J = 7.0 Hz, 2H), 2.87-2.89 (m, 2H) ppm. MS (ESI): m/z 553.7 [M+l]+.

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, 2-(3-Hydroxypropyl)isoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; EPIZYME, INC.; CHESWORTH, Richard; KUNTZ, Kevin, Wayne; OLHAVA, Edward, James; PATANE, Michael, A.; WO2012/82436; (2012); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 1074-82-4,Some common heterocyclic compound, 1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide, molecular formula is C8H4KNO2, 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.

Example 3: Preparation of 2-5 (S){2-oxo-3-[4-(3-oxo-morpholin-4-yl)-phenyl)-oxazolidin- 5-ylmethyI}-isoindole-l,3-dione (III)60 gms of 4-[4-(5-chloromethyl-2-oxo-oxazolidin-3-yl)-phen l]-mophiholin-3-one , potassium phthalimide (40 g) and Nu,Nu-dimethyl formamide (400 ml) were charged into a clean and dry 4 neck R.B. flask. The resultant reaction mixture was heated to reflux for about 5 hours. After completion of the reaction, the reaction mixture was cooled to about 30C, poured into 2 L of water and the solid separated was filtered to give 50 gms of the title compound

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Potassium 1,3-dioxoisoindolin-2-ide, its application will become more common.

Reference:
Patent; SYMED LABS LIMITED; MOHAN RAO, dodda; KRISHNA REDDY, pingili; ANNA REDDY, ambati; VENKAT REDDY, buthukuri; WO2012/32533; (2012); A2;,
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Indoline | C8H9N – PubChem

Related Products of 5428-09-1, 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. 5428-09-1, name is 2-Allylisoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: An oven-dried, two-necked round-bottom flask containing a stir bar was charged with an aryl bromide 1 (1.0 mmol), Pd(OAc)2 (6.8 mg, 0.03 mmol), K2CO3 (165.9 mg, 1.2 mmol), HQ (15.6 mg, 0.1 mmol), allylamine (1.2 mmol), and DMF (3.0 ml) under nitrogen at room temperature. Following degassing three times, the flask was placed in an oil bath, and the mixture was stirred and heated at the appropriate temperature. After an appropriate reaction time, the flask was removed from the oil bath and cooled to room temperature. Water (20 ml) was added, and the mixture was extracted with CH2Cl2 (3.x.20 ml). The combined organic layer was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. The product was purified by flash column chromatography on silica gel using ethyl acetate/hexane as an eluent.

The chemical industry reduces the impact on the environment during synthesis 2-Allylisoindoline-1,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Article; Jiang, Zhen; Zhang, Lingjuan; Dong, Chaonan; Ma, Baode; Tang, Weijun; Xu, Lijin; Fan, Qinghua; Xiao, Jianliang; Tetrahedron; vol. 68; 24; (2012); p. 4919 – 4926;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 17564-64-6,Some common heterocyclic compound, 17564-64-6, name is 2-(Chloromethyl)isoindoline-1,3-dione, molecular formula is C9H6ClNO2, 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 initial carbonyl compound (50 mmol) was dissolved/suspended in ethanol (50 mL) and magnetically stirred with thiosemicarbazide (50 mmol) and catalytic amounts of acetic acid for 8-24 h at room temperature. The obtained thiosemicarbazone was filtered, washed with appropriate solvent (n-hexane, petroleumether or diethyl ether) and dried under vacuum. The intermediate thiosemicarbazone (50 mmol) reacted with ethyl bromoacetate (50 mmol), in methanol (50 mL) and sodium acetate (50 mmol) at room temperature under magnetic stirring for 24 h. The resulting 4-thiazolidinone was poured on ice, filtered or extracted with chloroform (3 x 100 mL) and purified by column chromatography (SiO2, ethyl acetate/n-hexane). Then, the obtained thiazolidinone (50 mmol) was dissolved/suspended in 50 mL of anhydrous acetone in the presence of anhydrous potassium carbonate (50 mmol), and reacted with equimolar amounts of 4-nitrobenzyl bromide, 1-(chloromethyl)naphthalene and N-(chloromethyl)phthalimide for 24-48 h. The product was poured on ice, filtered or extracted with chloroform (3 x 50 mL) and purified by column chromatography (SiO2, ethyl acetate/n-hexane) in order to obtain the title compoundsin high yields. 7.1.55 2-((2-(2-(Pentan-2-ylidene)hydrazono)-4-oxothiazolidin-3-yl)methyl)isoindoline-1,3-dione (3C) White powder, mp 125-126 C, 84% yield; 1H NMR (400 MHz, CDCl3): delta 0.92-0.95 (t, 3H, CH3), 1.59-1.61 (m, 2H, CH2), 1.93 (s, 3H, CH3), 2.23-2.27 (t, 2H, CH2), 3.83 (s, 2H, CH2, thiazolidinone), 5.73 (s, 2H, ArCH2), 7.75-7.76 (m, 2H, Ar), 7.86-7.87 (m, 2H, Ar). 13C NMR (100 MHz, CDCl3): delta 13.8, 14.0, 17.5, 19.6, 19.8, 22.9, 32.2, 34.1, 40.6, 45.0, 45.1, 123.6, 131.7, 134.3, 158.0, 166.7, 170.0, 171.1.

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

Reference:
Article; De Monte, Celeste; Carradori, Simone; Bizzarri, Bruna; Bolasco, Adriana; Caprara, Federica; Mollica, Adriano; Rivanera, Daniela; Mari, Emanuela; Zicari, Alessandra; Akdemir, Atilla; Secci, Daniela; European Journal of Medicinal Chemistry; vol. 107; (2016); p. 82 – 96;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 2058-74-4, These common heterocyclic compound, 2058-74-4, name is 1-Methylisatin, 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 mixture of the Fe(III)(at)g-C3N4 nanocomposite (70 mg, 0.35 mmol based on Fe(III)) in aqueous media (3 ml) was dispersed for 30 min. Isatin (1 mmol) and indole (2.0 mmol) were added to the mixture and stirred in reflux conditions for an appropriate time. After the reaction was completed, the crude product was extracted with ethyl acetate and dried over anhydrous Na2SO4 followed by evaporation of the solvent. The pure products were achieved by recrystallization in hot ethanol and identified by IR, 1H & 13C NMR spectral data. The nanocomposite was washed with EtOH, dried, and reused for the next run.

Statistics shows that 1-Methylisatin is playing an increasingly important role. we look forward to future research findings about 2058-74-4.

Reference:
Article; Allahresani, Ali; Taheri, Bahare; Nasseri; Research on Chemical Intermediates; vol. 44; 11; (2018); p. 6741 – 6751;,
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. 3484-35-3, name is 5-Methylindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., Formula: C9H9NO

Under nitrogen protection, 0.5 mmol of raw 5-methyl-2-indolinone, 1.2 mmol of pinacol borane and catalyst Y [N(SiMe3) 2] 30.05 mmol, 3 mL of toluene, reacted at 120 C for 36 h, and the product isolation yield was 87%.

According to the analysis of related databases, 3484-35-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wenzhou Medical University; Zhang Junfang; Cai Wenxuan; (11 pag.)CN110818608; (2020); A;,
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. 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C9H4F3NO3

Weigh5-trifluoromethoxy ruthenium0.95g (0.0041mol),0.85 g (0.0043 mol) of 4-chloroindole anhydride was added to a 100 ml three-necked flask containing a magnet, and then 40 ml of chloroform was added to the three-necked flask.1.5 ml of triethylamine, heated to reflux in an oil bath at 80 C for 3 h, after the reaction is over,The heating was stopped, and the mixture was cooled, and suction filtered to obtain a crude yellow solid powder.The product was washed 3 times with 10 ml of ethanol to obtain a pure product of a yellow solid powder.Dry and weigh 0.92g,The yield was 60.1%.

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 169037-23-4.

Reference:
Patent; Northwest University; Wang Cuiling; Bai Xiao; Zhang Xiaobin; Liu Jianli; (16 pag.)CN110143964; (2019); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem