Indolines-derivatives

Application of 102359-00-2, A common heterocyclic compound, 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, molecular formula is C9H7NO3, 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 9a-d (2 mmol), EDCI (3 mmol) and HOBt (3 mmol) in dry DCM (20 mL) was stirred at 0C for 3.5 h. Then different substituted amines (2.2 mmol) and DIPEA (4 mmol) were added and the reaction was stirred at r.t. for another 1.5 h. The organic layer was washed with water and brine and dried over Na2SO4. Removal of the solvent gave a residue that was purified by column chromatography (silica gel, CH2Cl2-MeOH 100: 1 as an eluent) to furnish 10a-n as white solids.

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; Guo, Jing; Zhu, Mingyue; Wu, Tianxiao; Hao, Chenzhou; Wang, Kai; Yan, Zizheng; Huang, Wanxu; Wang, Jian; Zhao, Dongmei; Cheng, Maosheng; Bioorganic and Medicinal Chemistry; vol. 25; 13; (2017); p. 3500 – 3511;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 875003-43-3, These common heterocyclic compound, 875003-43-3, name is 7-Fluoro-1-methylindoline-2,3-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: First phenylacetylene (1 mmol) was stirred with Et3N (1 mmol) in CH3CN (5 mL) at roomtemperature. After 15-20 min, N-methyl isatin (1 mmol) and InBr3 (15 mol %)was added and the reaction mixture was stirred for 16-18 h. When N-methylisatin was completely consumed as indicated by TLC, phenyl-N-tosylmethanimine(1 mmol) was added and the reaction mixture was stirred untilthe reaction reached completion, as evidenced by TLC. Acetonitrile wasdistilled out under reduced pressure and the residue was purified by silicagel (mesh 60-120) chromatography (hexane-EtOAc) to afford thecorresponding products. Characterization data of representative compounds.

The synthetic route of 875003-43-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Siddiqui; Rahila; Rai, Pragati; Waseem, Malik A.; Abumhdi, Afaf A.H.; Tetrahedron Letters; vol. 56; 29; (2015); p. 4367 – 4370;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 923590-95-8, A common heterocyclic compound, 923590-95-8, name is 4-Bromoisoindoline hydrochloride, molecular formula is C8H9BrClN, 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: 4-Bromoisoindoline hydrochloride (3.0 g, 13 mmol, 1 eq) was suspended in dry DCM (50 ml), and then TEA (5.4 ml, 39 mmol, 3 eq) was added. Reaction mixture was cooled to 0C in an ice-bath, and then benzyl chloroformate (2.7 ml, 19 mmol, 1 .5 eq) dissolved in 10 ml DCM was added dropwise. Reaction was carried out under inert gas (nitrogen) atmosphere while stirring at room temperature for 3h. Reaction mixture was extracted thrice with saturated NaHCC solution, then once with water and with saturated NaCl solution. Organic phase was dried over anhydrous Na2S04, and then concentrated under reduced pressure to obtain white solid which was dried under vacuum. (0165) White solid, yield: 90% (3.8 g), Ci6Hi4BrN02, MW 332.19, monoisotopic mass 331 .02, [M+H]+ 332.2, UPLC Rt = 8.12. 1H NMR (300 MHz, CDCU) d (ppm) 4.73 (dd, J= 1 1 .6, 1 .4 Hz, 2H), 4.79-4.89 (m, 2H), 5.22 (d, J = 2.2 Hz, 2H), 7.09-7.50 (m, 7H).

The synthetic route of 923590-95-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CELON PHARMA S.A.; UNIWERSYTET JAGIELLONSKI; INSTYTUT FARMAKOLOGII POLSKIEJ AKADEMII NAUK; KAMINSKI, Krzysztof; GRYCHOWSKA, Katarzyna; CANALE, Vittorio; BOJARSKI, Andrzej J.; SATALA, Grzegorz; LENDA, Tomasz; POPIK, Piotr; MATLOKA, Mikolaj; DUBIEL, Krzysztof; MOSZCZYNSKI-PETKOWSKI, Rafal; PIECZYKOLAN, Jerzy; WIECZOREK, Maciej; ZAJDEL, Pawel; (69 pag.)WO2019/97282; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 4702-13-0, These common heterocyclic compound, 4702-13-0, name is N-Phthaloylglycine, 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.

7-b: 1-Bromo-3-phthalimide acetone 2-Phthalimide acetic acid 2.05 g (10.0 mmol), 10 mL of thionyl chloride,Placed in 50mL reaction flask, reflux to the remaining raw materials, vacuum drying, in a brown oil, add 2mL toluene. 15 mL of 50% by weight aqueous solution of KOH was added to 40 mL of diethyl ether, and 6.00 g (33. Mmol) of nitrosourea was slowly added in portions under ice-cooling. After addition, shaking was continued for 10 minutes. , & Lt;And dried for 2 hours in the form of flake KOH to obtain a solution of diazomethane in diethyl ether.The above-mentioned diazomethane-containing ether solution was placed in a 100 mL reaction flask and placed in an ice bath. 2 mL of a toluene solution containing the above oil was slowly added dropwise. The reaction was complete, filtered, rinsed with diethyl ether and the resulting solid spare. The solid was dissolved in 20 mL of tetrahydrofuran, and 2 mL of a 40 wt% aqueous solution of HBr was added dropwise to the reaction mixture, and the mixture was dried under reduced pressure. Add 100mL ethyl acetate, placed in a separatory funnel, respectively, saturated NaHC03, water, saturated NaCl solution, dried anhydrous Mg2S04. Dried under reduced pressure and recrystallized from 95% by weight ethanol to give 1.24 g of a white solid in 44.0% by weight yield.

The synthetic route of 4702-13-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Beijing Union Pharmaceutical Factory; Institute of Materia Medica, Chinese Academy ofMedical Sciences; Pan, Xiandao; Zhang, Peicheng; Yang, Yajun; Zhao, Limin; (20 pag.)CN102786464; (2016); B;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, molecular formula is C9H7NO3, 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: 102359-00-2

Into a 25-mL round-bottom flask was placed tert-butyl 4-aminopiperidine-1- carboxylate (300 mg, 1.50 mmol, 1.00 equiv), dichloromethane (10 mL), 2-oxo-2,3- dihydro-1H-indole-5-carboxylic acid (319 mg, 1.80 mmol, 1.20 equiv), EDCI (344 mg, 1.79 mmol, 1.20 equiv), and HOBT (304 mg, 2.25 mmol, 1.50 equiv). This was followed by the addition of TEA (454 mg, 4.49 mmol, 3.00 equiv) dropwise with stirring at 0oC. The resulting solution was stirred for 14 h at 20oC. The solids were collected by filtration. This resulted in 393 mg (73%) of tert-butyl 4-(2-oxo-2,3-dihydro-1H-indole-5- amido)piperidine-1-carboxylate as a yellow solid

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 102359-00-2, its application will become more common.

Reference:
Patent; Epizyme, Inc.; Poley, Megan Allen Clunan; Kunz, Kevin Wayne; Mills, James Edward John; Mitchell, Lona Helen; munckhof, Michael John; Harvey, Darren Martin; (303 pag.)KR2017/45749; (2017); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 71294-07-0,Some common heterocyclic compound, 71294-07-0, name is 5,6-Difluoroindolin-2-one, molecular formula is C8H5F2NO, 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.

5,6-difluoro-2,3-dihydro-1H-indole Under an argon atmosphere 0.30 g (1.8 mmol) 5,6-difluoro-1,3-dihydro-indol-2-one were dissolved in 10 mL THF and 3.0 mL of a 1 M borane in THF solution were added dropwise. Then the reaction mixture was heated for 2 h to 70 C. and then cooled. After the addition of 3 mL MeOH a further 5 mL of a 4N aqueous hydrochloric acid solution were added and the mixture was refluxed for 1 h. The organic phase was evaporated down, the aqueous phase was washed with DCM and then made alkaline with a 4N aqueous sodium hydroxide solution and extracted several times with EtOAc. The combined organic phases were dried on sodium sulphate, filtered and evaporated down. Yield: 160 mg (47% of theory) ESI-MS: m/z=156 (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 5,6-Difluoroindolin-2-one, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/195954; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 19155-24-9, name is 3,3-Dimethylindolin-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. Recommanded Product: 3,3-Dimethylindolin-2-one

(d) 3,3-Dimethyl-5-nitroindolin-2-one A solution of 22 ml. fuming nitric acid in 200 ml. 80percent sulphuric acid is added dropwise, with cooling, to a solution of 100 g. (0.62 mol) 3,3-dimethylindolin-2-one in 500 ml. 80percent sulphuric acid. The reaction mixutre is then stirred for about 30 minutes, poured on to ice, filtered with suction, washed with water and dried. Yield: 100 g. (78percent of theory); m.p. 192°-196° C. (ethyl acetate/heptane).

The synthetic route of 3,3-Dimethylindolin-2-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer Mannheim GmbH; US4666923; (1987); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 19727-83-4, A common heterocyclic compound, 19727-83-4, name is 6-Nitroindoline, molecular formula is C8H8N2O2, 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.

6-Aminoindoline A solution of 6-nitroindoline (1 g, 6.1 mmol) in 50 mL of ethyl acetate was hydrogenated under an atmosphere of hydrogen with Pd-C 10% (100 mg) at rt for 3 h. Filtration over celite afforded 1.0 g (98%) of 6-aminoindoline. Data for 6-aminoindoline: 1 H NMR (400 MHz, CDCl3) 7.40 (d, J=7.4, 1H), 6.05 (d, J=2.0, 1H), 6.03 (d, J=7.5, 1H), 3.67 (bs, 1H), 3.49 (t, J=8.1, 2H), 3.48 (bs, 2H), 2.90 (t, J=8.2, 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:
Patent; Ligand Pharmaceuticals Incorporated; US5688808; (1997); A;; ; Patent; Ligand Pharmaceuticals Incorporated; US5693646; (1997); A;; ; Patent; Ligand Pharmaceuticals Incorporated; US5693647; (1997); A;; ; Patent; Ligand Pharmaceuticals Incorporated; US5696127; (1997); A;,
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. 20870-79-5, name is 5-Nitroindolin-2-one, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H6N2O3

5-Nitro-2-oxindole (6.3 g) was hydrogenated in methanol over 10% palladium on carbon to give 3.0 g (60% yield) of 5-amino-2-oxindole as a white solid.

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; SUGEN, Inc.; US2002/183364; (2002); A1;,
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., Application In Synthesis of 5-Methylindolin-2-one

General procedure: The mixture of oxindole 1 (0.1 mmol), beta,gamma-unsaturated alpha-keto ester 2 (0.12 mmol),DABCO (0.02 mmol) in 1 mL H2O were stirred at room temperature. After stirringfor the indicated time, the mixture was extracted with ethyl acetate. The combinedorganic phase was dried over Na2SO4 and concentrated in vacuo. The residue wasfurther purified by washing with PE/EA to afford the desired products.

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 3484-35-3.

Reference:
Article; Han, Man-Yi; Pan, Ping; Sheng, Fei-Fei; Synlett; vol. 28; 11; (2017); p. 1378 – 1382;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem