Month: June 2021

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. 41910-64-9, name is 4-Chloroindoline, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H8ClN

A ImL {2-[4-({[(2,5-dioxopyrrolidin-l-yl)oxy]carbonyl}amino)-2- (l-methyl-lH-pyrazol-5-yl)phenoxy]ethyl}carbamate in dimethylformamide (78.8 mumol) was added to 4-chloroindoline (14.52mg, 1.2eq) and stirred at room temperature for 18hr. To this was added 2.0M hydrochloric acid in ether (197 muL, 5eq) and the reaction was stirred at room temperature for 24hr (2-3 drops of concentrated hydrochloric acid was added if the deprotection was incomplete and the resulting mixture was stirred for another 24hr). The ether and hydrochloric acid were evaporated under a stream of nitrogen and the resulting material was purified by etaPLC. The proper fractions were collected and lyophilized to afford the title compound as a white solid in 43.5% yield. LCMS m/z (%) = 412 (M+eta 35Cl, 100), 414 (M+eta 37Cl, 36). 1H NMR (400 MHz, DMSO-4) delta ppm 3.10 – 3.24 (m, 4 H), 3.71 (s, 3 H), 4.13 – 4.21 (m, 4 H), 6.34 (d, /=2.02 Hz, 1 H), 6.96 (d, /=8.08 Hz, 1 H), 7.13 – 7.21 (m, 2 H), 7.48 – 7.50 (m, 2 H), 7.64 (dd, /=8.84, 2.78 Hz, 1 H), 7.81 (d, /=7.58 Hz, 1 H), 7.92 (s, 2 H), 8.63 (s, 1 H).

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 41910-64-9.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; WO2007/136703; (2007); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 3676-85-5,Some common heterocyclic compound, 3676-85-5, name is 5-Aminoisoindoline-1,3-dione, molecular formula is C8H6N2O2, 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 stirred solution of 5-amino-1H-isoindole-1,3(2H)-dione (1.0 g, 6.2 mmol) dissolved in sulfuric acid solution (2 mL of Con. H2SO4 in 7.5 mL of H2O) at 0 C., was added ice cold sodium nitrite solution (0.8 g in 2 mL of H2O) dropwise. After 45 min of stirring at 0 C., CuBr (3.4 g, 23.7 mmol) and HBr[48%] (13.6 mL, 4 vol. w.r.t. CuBr) were added at the same temperature. The resulting mixture was stirred at 80 C. for 8 h then poured into crushed ice. Filtered the solid, washed with ice cold water and dried thoroughly to give 0.6 g (43.0%) of 5-bromo-1H-isoindole-1,3(2H)-dione as a brown colour solid.

The synthetic route of 3676-85-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Deng, Jianghe; Kerns, Jeffrey K.; Jin, Qi; Lin, Guoliang; Lin, Xichen; Lindenmuth, Michael; Neipp, Christopher; Nie, Hong; Thomas, Sonia M.; Widdowson, Katherine L.; US2009/143372; (2009); 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. 16800-68-3, name is 1-Acetylindolin-3-one, This compound has unique chemical properties. The synthetic route is as follows., Formula: C10H9NO2

3 – (2 – Bromophenyl) propyne acid 4 – nitrophenyl-unitz (103.5 mg 0.3 mmol), was obtained. N- Acetylindole -3 -unitz 26.3 mg (0.15 mmol), the carbene-unitz (0.015 mmol), 3.96 mg, 1 diazabicycloundecene 8 – (-7 -) and methylene-methylene chloride shown in Formula 45 mul IV 0.3 mmol were placed in 3 ml a 25 ml unitunito-two-port 2h bottle, and reacted 30 C, under unituniteous conditions, and concentrated, under inert atmosphere protection, unitant-like conditions. The eluate fractions of all the products 10:1 detected were collected by chromatography with petroleum ether: ethyl acetate in the timetime as eluent column chromatography, and the solvent was evaporated to obtain the residue unit, 28 mg and gave rise 50% to unit_.

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 16800-68-3.

Reference:
Patent; China Pharmaceutical University; Du Ding; Sun Kewen; (10 pag.)CN110156800; (2019); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 1035235-27-8, name is tert-Butyl 4-bromoisoindoline-2-carboxylate belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Product Details of 1035235-27-8

tert-Butyl 4-bromoisoindoline-2-carboxylate (163 mg, 0.548 mmol), methyl 3-hydroxybenzoate (100 mg, 0.657 mmol), di-tert-butyl(2?,4?,6?-triisopropyl-[1,1?-biphenylj-2-yl)phosphine (23 mg, 0.055 mmol), palladium(II) acetate (12 mg, 0.055 mmol) and potassium phosphate (233 mg, 1.10 mmol) were added to a vial, which was then evacuated and back-filled with argon three times. Degassed toluene (1.8 mL) was added. The reaction mixture was stirred at 115 C for 16 h. The reaction mixture wasdiluted with DCM, filtered, and purified by flash chromatography to give 231A (55 mg,27%) as a colorless oil. MS(ESI) m/z 269.9 (M-Boc+H).

The synthetic route of 1035235-27-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SMALLHEER, Joanne, M.; SHAW, Scott, A.; HALPERN, Oz, Scott; HU, Carol, Hui; KICK, Ellen, K.; (311 pag.)WO2017/40449; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 118289-55-7, A common heterocyclic compound, 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one, molecular formula is C10H9Cl2NO, 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.

Example 1 Synthesis of Ziprasidone To a 125 mL round bottom flask equipped with an N2 inlet and condenser are added 0.73 g (3.2 mmol) 5-(2-chloroethyl)-6-chloro-oxindole, 0.70 g (3.2 mmol) N-(1,2-benzisothiazol-3-yl)piperazine, 0.68 g (6.4 mmol) sodium carbonate, 2 mg sodium iodide, and 30 mL methylisobutyl ketone. The reaction is refluxed for 40 hours, cooled, filtered, and evaporated. The residue is chromatographed on silica gel, eluding the by-products with ethyl acetate (1 L) and the product with 4% methanol in ethyl acetate (1.5 L). The product fractions (Rf=0.2 in 5% methanol in ethyl acetate) are evaporated, taken up in methylene chloride, and precipitated by addition of ether saturated with HCl; the solid is filtered and washed with ether, dried, and washed with acetone. The latter is done by slurrying the solid with acetone and filtering.

The synthetic route of 118289-55-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Barberich, Timothy J.; Rubin, Paul D.; Yelle, William E.; US2006/19970; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 675109-26-9, name is 6-Bromoisoindolin-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. HPLC of Formula: C8H6BrNO

TDI01239-1 (500 mg, 2.358 mmol) was dissolved in tetrahydrofuran (24 mL), and cooled to 0 C. Under theprotection of nitrogen, 60% NaH (236 mg, 5.895 mmol) was added to the above reaction solution, and the reaction wasperformed at room temperature for 1h after the addition. Bromoethyl acetate was then added at 0 C, and the reactionwas continued at room temperature for 2h. LC-MS indicated the reaction was complete. After completion of the reaction,ice water and IN HCl solution was added to quench the reaction, and the aqueous phase was extracted with ethyl acetate(15 mL). The combined organic phase was washed with saturated brine, dried over anhydrous sodium sulfate andconcentrated to dryness to afford TDI01239-2 (700 mg, yellow solid, yield: 99.57%). MS m/z (ESI): 298.1 [M+H].

The synthetic route of 6-Bromoisoindolin-1-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Beijing Tide Pharmaceutical Co., Ltd.; Zhao, Yanping; Wang, Hongjun; Li, Gong; Jiang, Yuanyuan; Li, Xiang; Zhou, Liying; Liu, Yanan; (235 pag.)EP3421465; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 24566-79-8, These common heterocyclic compound, 24566-79-8, name is N-(6-Bromohexyl)phthalimide, 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 mixture of the intermediates 3a-3e (5 mmol) and corresponding secondary amine 4a-4g (5.5 mmol) was added in CH3CN (20 ml) at the presence of anhydrous K2CO3 (6 mmol). The mixture was heated at 65 C for 6-10 h. The solvent was evaporated in vacuo. The residue was dissolved in CH2Cl2 (25 mL), washed with water (20 mL × 3), and the combined organic phases were washed with saturated aqueous NaCl (30 mL), dried over sodium sulfate, and filtered. The solvent was evaporated under reduced pressure. The residue was purified on a silica gel chromatography using mixtures of petroleum/acetone as eluent to get the target products TM-1~TM-28.

Statistics shows that N-(6-Bromohexyl)phthalimide is playing an increasingly important role. we look forward to future research findings about 24566-79-8.

Reference:
Article; Sang, Zhipei; Wang, Keren; Wang, Huifang; Yu, Lintao; Wang, Huijuan; Ma, Qianwen; Ye, Mengyao; Han, Xue; Liu, Wenmin; Bioorganic and Medicinal Chemistry Letters; vol. 27; 22; (2017); p. 5053 – 5059;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 883-44-3,Some common heterocyclic compound, 883-44-3, name is 2-(3-Hydroxypropyl)isoindoline-1,3-dione, molecular formula is C11H11NO3, 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 solution of 4-[(4-fluorophenyl)sulfonyl]tetrahydro-2H-pyran-4-carboxylic acid, 1,I-di-methylethyl ester (6.7 g, 19 mmol, as prepared in Example 1, Part C) in anhydrous N,N-dimethylformamide (40 ml) at ambient temperature was added N-(3-hydroxypropyl)phthalimide (4 g, 19 mmol), followed immediately by NaH (700 mg, 20 mmol, 60% dispersion in mineral oil). After 1.5 hr, HPLC showed less than 1% of the starting Electrophile. The reaction mixture was quenched with water (60 ml). The cloudy mixture was extracted with ethyl acetate (2×100 ml). The organic layers were combined, washed with brine (1×200 ml), dried over sodium sulfate, filtered, and concentrated in vacuo to give a tan, viscous oil that crystallized from methanol (3.2 g, 52%). ESMS m/z=489 [M+H]+. This material was used without further purification.

The synthetic route of 883-44-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Freskos, John N.; Fobian, Yvette M.; Barta, Thomas E.; Becker, Daniel P.; Bedell, Louis J.; Boehm, Terri L.; Carroll, Jeffery N.; DeCrescenzo, Gary A.; Hockerman, Susan L.; Kassab, Darren J.; Kolodziej, Steve A.; McDonald, Joseph; Mischke, Deborah A.; Norton, Monica B.; Rico, Joseph G.; Talley, John J.; Villamil, Clara I.; Wang, Lijuan Jane; US2004/10019; (2004); 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. 552330-86-6, name is 5-Bromoisoindolin-1-one, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 5-Bromoisoindolin-1-one

A mixture of 5-bromoisoindolin-1-one (2-73, 200 mg, 0.95 mmol), 4,4,4?,4?,5,5,5?,5?-octamethyl-2,2?-bi(1,3,2-dioxaborolane) (2-57, 241 mg, 0.95 mmol), KOAc (186 mg, 1.9 mmol), and Pd(dppf)C12 (69 mg, 0.095 mmol) in dioxane (5 ml) was stirred for 16 h at 60 C. Upon reaction completion, the resulting mixture was washed with H20 and extracted with ethyl acetate (50 mL x 3). The combined organic phases were concentrated under reduced pressure and the resulting residue was purified via silica gel chromatography (Pet Ether/ ethyl acetate = 10/1) to obtain intermediate 2-74 (white solid, 300 mg, 88% yield). LCMS (m/z): 260 [M + Hj.

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 552330-86-6.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; FONDAZIONE CENTRO SAN RAFFAELE; GRAY, Nathanael S.; BUHRLAGE, Sara; ANDERSON, Kenneth; COTTINI, Francesca; TONON, Giovanni; (288 pag.)WO2016/161145; (2016); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 59-48-3, 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 59-48-3 as follows.

PREPARATION 8 5-Acetyl-2-oxindole To 95 ml. of carbon disulfide was added 27 g. (0.202 mole) of aluminum chloride, followed by the dropwise addition of a solution of 3 ml. (0.042 mole) of acetyl chloride in 5 ml. of carbon disulfide, with stirring. Stirring was continued for 5 minutes and then 4.4 g. (0.033 mole) of 2-oxindole was added. The resulting mixture was heated under reflux for 4 hours and cooled. The carbon disulfide was removed by decantation and the residue was triturated under water and recovered by filtration. After drying, 3.2 g. of the title compound was obtained, m.p. 225-227 C.

According to the analysis of related databases, 59-48-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pfizer Inc.; US4652658; (1987); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem