Category: indolines-derivatives

Electric Literature of 7477-63-6, 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. 7477-63-6, name is 7-Chloroisatin belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

In 25 ml sealed tube by adding 1 a (0.5 mmol, 88.6 mg), 2 i (0.5 mmol, 90.8 mg), iodine simple substance (0.25 mmol, 63.5 mg), triethylamine (0.25 mmol, 25.3 mg) and chlorobenzene (2 ml), then put into 130 C in oil bath stirring reaction 10 h. Add 50 ml water quenching reaction, extracted with ethyl acetate (50 ml ¡Á 3), the organic phase after the mass concentration is 10% of Na2 S2 O3 Solution and saturated salt water are successively washing, drying with anhydrous sodium sulfate. Filtering, turns on lathe does, too separating by silica gel column (petroleum ether/ethyl acetate=5/1) to obtain the target product 3 u (79.2 mg, 56%). The compound of the characterization data are as follows:

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, 7-Chloroisatin, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Xinxiang Medical University; Gao Qinghe; Liu Xingxia; Liu Zhaomin; Yang Limin; Yuan Huan; He Shuang; (16 pag.)CN107501180; (2017); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 1029691-06-2, name is 2-(3-Oxocyclopentyl)isoindoline-1,3-dione, molecular formula is C13H11NO3, 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. COA of Formula: C13H11NO3

Reference Synthesis Example 221 (0990) 3-(1,3-Dioxoisoindolin-2-yl)cyclopenta-1-en-1-yl trifluoromethanesulfonate (0991) To a dichloromethane solution (30 mL) of 2-(3-oxocyclopentyl)isoindoline-1,3-dione (1.08 g, 4.71 mmol), trifluoromethanesulfonic acid anhydride (1.16 mL, 7.06 mmol) and N,N-diisopropylethylamine (1.16 mL, 9.42 mmol) were added at 0 C. and the resultant mixture was stirred at 0 C. for 1 day. After completion of the reaction, the reaction solution was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1) to obtain the title compound (780 mg, yield 46%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1029691-06-2, its application will become more common.

Reference:
Patent; NISSAN CHEMICAL INDUSTRIES, LTD.; Saito, Noriko; Egi, Jun; Nagai, Hiroshi; Ueno, Megumi; Shintani, Yusuke; Inaba, Yusuke; Adachi, Michiaki; Hirai, Yuichi; Kawazu, Takeshi; Yasutake, Koichi; Takahashi, Daiki; (220 pag.)US9403798; (2016); B2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

2058-72-2, name is 5-Bromo-1-methylindoline-2,3-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. Formula: C9H6BrNO2

General procedure: A 5 mL of two-necked flask with 25 mg of freshly activated 4A molecular sieves and micro stirbar was flame heated under vacuum and refilled with Nitrogen. Isatin derivative (0.10 mmol, in 0.5 mL of benzene, 0.5 M) was charged to the cooled round bottom under argon, followed by addition of carbamoylsilane (0.15 mmol) in 0.1 mL of benzene. The sealed reaction mixture was stirred at 60 C until no isatin derivatives could be detected by TLC. Volatiles were removed in vacuum to afford the crude product which was purified by column chromatography on silica gel (petroleum ether/ethyl acetate combination) to give compound 3.6

The synthetic route of 2058-72-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liang, Jin-Yan; Wang, Hui; Yang, Yan-Li; Shen, Shou-Jie; Chen, Jian-Xin; Tetrahedron Letters; vol. 58; 27; (2017); p. 2636 – 2639;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

337536-15-9, name is 4-Bromoisoindolin-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. Safety of 4-Bromoisoindolin-1-one

Step 4: tert-butyl 4-bromo-1,3-dihydro-2H-isoindole-2-carboxylate To a solution of 4-bromoisoindolin-1-one (4 mmol) in THF (8 mL) was added borane-dimethyl sulfide complex (2M in THF, 14 mL) at 0 C. The reaction mixture was allowed to stir at reflux overnight and was then cooled to 0 C. The reaction mixture was quenched by the slow addition of MeOH (2 mL) and then 3N HCl. The reaction mixture was allowed to stir at reflux for 3 hr and then concentrated. Water was added to the residue and the pH of the solution was adjusted to >9 with 4N NaOH. The solution was extracted with diethyl ether. The organic solutions from this basic extraction were combined, dried over Na2SO4, filtered and concentrated to give 4-bromoisoindoline, which was dissolved in THF (5 mL). To this solution was added potassium carbonate (4 mmol) in water (0.5 mL), and BOC2O (2 mmol). The reaction mixture was allowed to stir at rt overnight. The reaction mixture was diluted with EtOAc, washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give tert-butyl 4-bromo-1,3-dihydro-2H-isoindole-2-carboxylate (0.8 mmol, 20%).

The synthetic route of 337536-15-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Millennium Pharmaceuticals, Inc.; US2008/171754; (2008); 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 appropriate oxindole (7a-e, 0.3 mmol) in ethanol (3 mL) was added corresponding aldehydes (11a-e,0.32 mmol) and a catalytic amount of piperidine. The reaction mixture was stirred at reflux for 6-12 h (reaction monitored byTLC). After cooling, the precipitate was filtered, washed with cold ethanol, and dried in air to furnish pure (Z)-3-(3′-methoxy-4′-(2-amino-2-oxoethoxy)-benzylidene)indolin-2-ones title compounds of formula (4a-v) as yellow/brown/orange solids in moderate to excellent yields.

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; Senwar, Kishna Ram; Reddy, T. Srinivasa; Thummuri, Dinesh; Sharma, Pankaj; Naidu; Srinivasulu, Gannoju; Shankaraiah, Nagula; European Journal of Medicinal Chemistry; vol. 118; (2016); p. 34 – 46;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 317-20-4, 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. 317-20-4, name is 7-Fluoroisatin belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: In an oven dried reaction vial, ligand 1d (2.5 mol%) was dissolved in dry toluene (1 mL), and to the resulting solution Ti(OiPr)4(5 mol%) was added and the resulting solution was stirred for 2 hunder N2 at RT. To the above stirred solution (Ia)/isatin (0.17 mmol) was added and the stirring was further continued for another 30 min. After that, DMP (0.19 mmol) was added dropwise to the above solution over 30 min. While in the case of isatin derived ketimines, initially ligand 1d (2.5 mol%) was dissolved in dry toluene (1 mL), and Ti(OiPr)4(5 mol%) was added to it and the resulting solution was stirred for 2 h at RT. Then 4 A MS (20 mg)and isatin derived ketimines (IVa) were added under stirring condition. After 30 min, DPP (IIb) was added over a period of 30 min.The reaction was monitored by TLC using hexane/ethyl acetate(70/30) as eluent. After the completion of the reaction, the solvent was removed on a rotary evaporator, and the product was purified by flash column chromatography on a silica gel column(eluted with hexane/ethyl acetate = 70/30). The purified products were characterized by LCMS and NMR.

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, 7-Fluoroisatin, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Nazish, Mohd; Jakhar, Ajay; Khan, Noor-Ul H.; Verma, Shailesh; Kureshy, Rukhsana I.; Abdi, Sayed H.R.; Bajaj, Hari C.; Applied Catalysis A: General; vol. 515; (2016); p. 116 – 125;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 16800-68-3, These common heterocyclic compound, 16800-68-3, name is 1-Acetylindolin-3-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 10 mL glass tube equipped with a stirring bar was charged with the isatin-derived N-Boc ketimine 1 (0.44 mmol, 1.2 equiv), the N-acetylindolin-3-one 2 (0.4 mmol, 1.0 equiv), catalyst 4o (0.02 mmol, 2 mol%) and CH2Cl2 (4.0 mL). The resulting solution was stirred at r.t. for the indicated time. The solvent was then evaporated to give the crude product, which was directly purified by flash chromatography (n-pentane/EtOAc, 4:1 to 1:1) to provide the desired products 3a-t.

The synthetic route of 16800-68-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gajulapalli, V. Pratap Reddy; Jafari, Ehsan; Kundu, Dipti S.; Mahajan, Suruchi; Peuronen, Anssi; Rissanen, Kari; Enders, Dieter; Synthesis; vol. 49; 22; (2017); p. 4986 – 4995;,
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 7477-63-6 as follows. Quality Control of 7-Chloroisatin

General procedure: A magnetically stirred mixture of naphthalene-1-amine (1.0mmol), isatin (1.0 mmol), dialkyl acetylenedicarboxylate (1.2 mmol) andanhydrous antimony trichloride (0.10 mmol) in dry acetonitrile (3 mL) taken ina 25 mL round bottom flask fitted with a reflux condenser and argon atmosphere and was refluxed for 5h and followed by usual work up and column chromatographyof the crude residue over silica gel (25 percent ethyl acetate in petroleum ether) toafford the pure products (5).

According to the analysis of related databases, 7477-63-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Karmakar, Rajiv; Kayal, Utpal; Bhattacharya, Biswajit; Maiti, Gourhari; Tetrahedron Letters; vol. 55; 7; (2014); p. 1370 – 1372;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide, 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. COA of Formula: C8H4KNO2

To a stirred solution of 1,6-dibromohexane (12.3 mL, 81.0 mmol) in DMF (10 mL), was added potassium phthalate (5.0 g, 27.0 mmol) portion-wise over 30 min at room temperature. After complete addition, the reaction mixture was stirred at 90 C for 18 h, then quenched with water (300 mL) and extracted with diethyl ether (150 mL x 2). The combined organic extracts were washed with water (100 mL x 2), followed by brine (50 mL x 2) and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resultant residue was purified by silica gel column chromatography (60-120 mesh) using 5-10% EtOAc / hexanes to afford 3-i as an off- white solid (6.3 g, 76% yield). LCMS: 310.95 (M+l).

The synthetic route of Potassium 1,3-dioxoisoindolin-2-ide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CV6 THERAPEUTICS (NI) LIMITED; SPYVEE, Mark; (500 pag.)WO2018/98206; (2018); A1;,
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