Month: July 2021

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;,
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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

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;,
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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;,
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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

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;,
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Indoline | C8H9N – PubChem

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

Synthetic Route of 5332-26-3, A common heterocyclic compound, 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, molecular formula is C9H6BrNO2, 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.

Into a solution of hexamethyldisilazane (17.5 g, 106 mmol) in THF (100 mL) was added n-butyllithium (1.58 M in hexane, 50 mL, 78.5 mmol) at -78 C. After 5 min at -78 C., the solution was allowed to warm to 0 C. for 30 min and then cooled to -78 C. again. A solution of 3-benzoyl-4-methyl-2-phenyl-1,3-oxazolidin-5-one (dried overnight in vacuo before using, 20 g, 71 mmol) in THF (250 mL) was added slowly under argon, and the dark red brown solution was stirred at this temperature for 3 h. A solution of N-(bromomethyl)phthalimide (22.2 g, 92.5 mmol) in THF (200 mL) was then added dropwise. The reaction mixture was allowed to warm to 20 C. in 4 h and stirred at this temperature overnight. The solvent was evaporated. The residue was dissolved in 10% NH4Cl (250 mL) and extracted with CH2Cl2. The organic phase was dried over Na2SO4 and evaporated. Recrystallization from CH2Cl2 and ether (1:4) gave white crystals of 2-((3-benzoyl-4-methyl-5-oxo-2-phenyloxazolidin-4-yl)methyl)isoindoline-1,3-dione (23 g, 74%). LC-MS (ES, m/z): 441 [M+H]+.

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

Reference:
Patent; FerroKin BioSciences, Inc.; US2011/275636; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 18711-13-2, These common heterocyclic compound, 18711-13-2, name is 4,7-Dichloroindoline-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.

To a mixture of sodium hydride (0.17 g, 6.94 mmol, 60% dispersion in mineral oil) in anhydrous N, Lambda/-dimethylformamide (5.00 mL) was added a solution of 4,7- dichloro-1/-/-indole-2,3-dione (1.00 g, 4.60 mmol) in N, Lambda/-dimethylformamide (5.00 mL) at 0 0C. The brown reaction mixture was stirred for 0.5 h followed by the addition of a solution of 1-bromopentane (0.84 g, 5.55 mmol) in anhydrous N, Lambda/-dimethylformamide (5.00 mL). The reaction mixture was stirred at ambient temperature for 16 h and poured into wet ethyl ether (30.0 mL). After the organic layer was separated, it was washed with water (2 x 20 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to dryness. The gummy residue was dried under vacuum and the solid was triturated with ether to give the title compound (0.98 g, EPO 98%): MS (ES+) m/z 286.2 (M + 1).

Statistics shows that 4,7-Dichloroindoline-2,3-dione is playing an increasingly important role. we look forward to future research findings about 18711-13-2.

Reference:
Patent; XENON PHARMACEUTICALS INC.; WO2006/113864; (2006); A2;,
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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. 923590-95-8, name is 4-Bromoisoindoline hydrochloride belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 923590-95-8

A solution of 4-bromoisoindoline hydrochloride (8.00 g, 34.33 mmol) in dichloromethane (20 mL) and triethylamine (14.3 mL, 103.0 mmol) was cooled to 0 C, and then di-tert-butyl dicarbonate (15.0 g, 68.73 mmol) was added. The mixture stirred overnight at room temperature and was then quenched by the addition of 50 mL of water. The resulting solution was extracted with 3×50 mL of dichloromethane, washed with 1×50 mL of brine, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified via column chromatography on silica gel (eluting with ethyl acetate/petroleum ether (1 :5)) to afford tert-butyl 4-bromoisoindoline-2-carboxylate (9 g, 75%) as a white solid. MS: (ESI, m/z): 242 [M-t-Bu+H]+

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

Reference:
Patent; FORMA THERAPEUTICS, INC.; ZHENG, Xiaozhang; MARTIN, Matthew W.; NG, Pui Yee; THOMASON, Jennifer R.; HAN, Bingsong; RUDNITSKAYA, Aleksandra; LANCIA, JR., David R.; (180 pag.)WO2019/204550; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem