Category: indolines-derivatives

Synthetic Route of 3484-35-3, A common heterocyclic compound, 3484-35-3, name is 5-Methylindolin-2-one, molecular formula is C9H9NO, 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: Appropriate indolin-2-one or indoline-2-thione (0.3 g) was mixed with acetic anhydride (3 mL) and 4-dimethylaminopyridine (DMAP, 1 mol %). The mixture was heated at 150 C in a round-bottomed flask equipped with an air condenser and CaCl2 guard tube. The reaction time for each reactant is provided in [Table 2] and [Table 3]. After the completion of the reaction excess acetic anhydride was evaporated under reduced pressure. The solid residue obtained in the case of the triacetylated products was suspended in cold methanol and vacuum filtered. The product collected was thoroughly washed with hexane and dried. In the case of mono and diacetylated products the solid residue was purified using flash column chromatography (FCC) (silica gel, hexanes/ethyl acetate).

The synthetic route of 3484-35-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jha, Mukund; Chou, Ting-Yi; Blunt, Brian; Tetrahedron; vol. 67; 5; (2011); p. 982 – 989;,
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 1168150-46-6 as follows. Computed Properties of C18H15NO4

(E)-methyl- 3-(methoxy(phenyl) methylene)-2-indolone-6- methyl formate (9-2) (200mg, 0.64mmol) and N- (4-aminophenyl) -N-methyl-2- (4- Trideutero methylpiperazin-1-substituted) acetamide (15-2) (171mg, 0.65mmol) in methanol (1.8mL) was refluxed for 8h , slowly cooled to 10 , stirring was continued at 10 1h, suction filtered, washed with cold methanol, and dried to give 310mg (89%) as a yellow solid, compound (Zeta)-3-((4-(Nu- methyl-2-(4- Trideutero methylpiperazin-1-substituted) acetamide)anilino(phenyl) methylene)-2-indolone-6- methyl formate

According to the analysis of related databases, 1168150-46-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sichuan University; Chen, Yuanwei; Xie, Yongmei; Wei, Yuquan; (32 pag.)CN104003925; (2016); B;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 2307-00-8,Some common heterocyclic compound, 2307-00-8, name is 5-Amino-2-methylisoindoline-1,3-dione, molecular formula is C9H8N2O2, 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.

4-Amino-N-methylphthalimide (1.0 g, 5.78 mmol) and 1,2-dibromoethane (2.17 mL, 25.2 mmol) were dissolved in anhydrous DMF (15 mL). The resulting reaction mixture was heated at 100 C. under argon for 12 h. After cooling to room temperature, the mixture was treated with 5 ml of saturated sodium bicarbonate and 50 mL of deionized water. Then it was extracted with EtOAc (30 mL) twice. The organic layers were combined and washed with brine, dried over MgSO4, concentrated, chromatographed on silica gel column using 30%(v/v) of EtOAc in hexane to give 13 (0.21 g, 13%): m.p. 212-214 C.; 1H NMR (CDCl3) delta 3.11 (s, 3H), 3.58 (t, 2H), 3.69 (t, 2H), 4.87 (broad, 1H), 6.75 (d, 1H), 7.00 (s, 1H), 7.60 (d, 1H). Anal. C11H11BrN2O2, calcd. C 46,67, H 3.92, N 9.89, found C 46.48, H 3.97, N 9.83.

The synthetic route of 2307-00-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mills, Randell L.; Wu, Guo-Zhang; US2005/80260; (2005); 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. 56341-37-8, name is 6-Chlorooxindole, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 6-Chlorooxindole

General procedure: A reaction mixture of the proper substituted indolin-2-ones 6,aldehyde (1.2 eq.), and piperidine (0.1 eq.) in ethanol (1 mL/0.5 mmol oxindole) was refluxed for 3-5 h, under nitrogen atmosphere. After, the mixture was cooled and put on ice, where the product precipitated. The product was filtered in vacuum with cold ethanol [10,14-17]. Finally, the product was placed in the vacuum desiccators to give the expected compound. The indolin-2-ones 3e was generated through substituted isatin in the presence of hydrazine monohydrate and ethylene glycerol, under reflux [18].

According to the analysis of related databases, 56341-37-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Nunes, Rute C.; Ribeiro, Carlos J.A.; Monteiro, Angelo; Rodrigues, Cecilia M.P.; Amaral, Joana D.; Santos, Maria M.M.; European Journal of Medicinal Chemistry; vol. 139; (2017); p. 168 – 179;,
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 2058-72-2 as follows. Formula: C9H6BrNO2

General procedure: The mixture of corresponding 2-amino-4-arylimidazoles 1 (1.0 mmol), isatin 18 (1.0 mmol) andmalononitrile 12 (1.0 mmol) in 2 mL of 2-propanol was refluxed during 50-60 min. After cooling, the solid products 19 were filtered off and crystallized from iPrOH.

According to the analysis of related databases, 2058-72-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Lipson, Victoria V.; Pavlovska, Tetiana L.; Svetlichnaya, Nataliya V.; Poryvai, Anna A.; Gorobets, Nikolay Yu.; Van Der Eycken, Erik V.; Konovalova, Irina S.; Shiskina, Svetlana V.; Borisov, Alexander V.; Musatov, Vladimir I.; Mazepa, Alexander V.; Beilstein Journal of Organic Chemistry; vol. 15; (2019); p. 1032 – 1045;,
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. 41910-64-9, name is 4-Chloroindoline, A new synthetic method of this compound is introduced below., Product Details of 41910-64-9

A suspension of 4-chloroindoline (1.00 g) and D-galactose (1.94 g) in H2O (3.0 ml)-ethyl alcohol (20 ml) was refluxed for 29 hours under argon atmosphere. The solvent was evaporated under reduced pressure to give crude 4-chloro-1-(beta-D-galactopyranosyl)indoline, which was used in the subsequent step without further purification.

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; Tanabe Seiyaku Co., Ltd.; US2008/27014; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 181140-34-1,Some common heterocyclic compound, 181140-34-1, name is (R)-(-)-N-(2,3-Epoxypropyl)phthalimide, 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.

A solution of 243.9 g (0.75 mol) of S – (+) – N- (2,3-ethoxypropyl) phthalimide (SM1), 105.1 g(0.500 mol) of 2- (2- (4-aminophenylamino) ethoxy) acetic acid were added to 3 L of a three-necked flask, followed by addition of anhydrous ethanol (1.8 L) and heated at 75 to 85 C for 24 h. With tap water to 40 ~ 45 C , filter, washed with ethanol, filter cake, white solid. And dried at 50 to 60 C under reduced pressure for 5 hours. 165.4 g of compound V was obtained in a yield of 80.0%.

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

Reference:
Patent; Chongqing Zhien Pharmaceutical Co., Ltd.; Deng Xianglin; Li Daming; Huang Chaoming; Huang Minghui; Feng Yongmei; Wang Fei; Liao Xingting; (29 pag.)CN106432218; (2017); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

132898-96-5, name is 2,3-Dioxoindoline-5-sulfonyl chloride, 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. HPLC of Formula: C8H4ClNO4S

To a stirred solution of 19b (0.15 g, 0.5 mmol) in dry DCM (4 mL) cooled in an ice bath was added TFA (0.6 mL, 10 mmol). After 1 h bulk solvent was removed in vacuo and the residue remaining taken up in dry DCM (8 mL) and cooled in an ice bath. Dry triethylamine (1.5 mL) was then added followed by 5-chlorosulfonylisatin8(0.16 g, 0.65 mmol) in dry THF (4 mL) and the solution was then stirred. After 19 h bulk solvent was removed in vacuo and redissolved in DCM (10 mL), washed with water (2×10 mL), then brine (1×10 mL) and dried over Na2SO4. Chromatography (hexanes/ethyl acetate) gave the desired product as an orange solid (104 mg, 51%).

The synthetic route of 132898-96-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IMPERIAL INNOVATIONS LIMITED; HAMMERSMITH IMANET LIMITED; ABOAGYE, ERIC OFORI; SMITH, GRAHAM; NGUYEN, QUANG-DE; ARSTAD, ERIK; GLASER, MATTHIAS EBERHARD; (78 pag.)JP5667056; (2015); B2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 21857-45-4, 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 21857-45-4 as follows.

7-Benzyl-4-chloro-2-methyl-5H-pyrrolo[3,2-d]pyrimidine 11 15(0.1 g, 0.39 mmol) and 5-methoxyindoline (58 mg, 0.48 mmol) were dissolved in isopropanol (15 mL) and heated at reflux for 12 h, and the solvent was evaporated in vacuo. The crude material obtained was purified by column chromatography and eluted with 1% (v/v) MeOH/CHCl3. Fractions containing the product (TLC) were pooled, and the solvent was evaporated to afford 4 (109 mg, 76%). TLC Rf 0.4 (MeOH: CHCl3; 1:20).

According to the analysis of related databases, 21857-45-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Pavana, Roheeth Kumar; Choudhary, Shruti; Bastian, Anja; Ihnat, Michael A.; Bai, Ruoli; Hamel, Ernest; Gangjee, Aleem; Bioorganic and Medicinal Chemistry; vol. 25; 2; (2017); p. 545 – 556;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 99365-40-9, These common heterocyclic compound, 99365-40-9, name is 6-Bromoindolin-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.

Four microwave vials were loaded as follows: 6-Bromoindolin-2-one (500 mg, 2.36 mmol), bis(pinacolato)diboron (898 mg, 3.54 mmol), potassium acetate (694 mg, 7.07 mmol) and Pd(dppf)Cl2*CH2Cl2 (96.0 mg, 0.118 mmol) were dissolved in DME (17 mL). The reaction was heated at 80 C overnight. The content of the four vials was then combined, concentrated and purified by column chromatography (cyclohexane/EtOAc) to afford the title compound as a white solid (2.27 g, 75%, purity 80%). 1 H NMR (500 MHz, CDCl3) ppm = 8.57 (bs, 1 H), 7.48 (d, J=7.3, 1 H), 7.31 (s, 1 H), 7.23 (d, J=7.3, 1 H), 3.55 (s, 2H), 1.33 (s, 12H). LC – MS (ESI, m/z) Rt = 2.75 min – 260 (M+H)+ (HPLC method B).

The synthetic route of 99365-40-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK PATENT GMBH; CANCER RESEARCH TECHNOLOGY LIMITED; SCHIEMANN, kai; STIEBER, Frank; BLAGG, Julian; MALLINGER, Aurelie; WAALBOER, Dennis; RINK, Christian; CRUMPLER, Simon Ross; WO2014/63778; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem