Month: May 2021

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. 3416-57-7, name is 2-(2-Oxopropyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Recommanded Product: 2-(2-Oxopropyl)isoindoline-1,3-dione

N-acetonylphthalimide (1 g, 4.9 mmol) was dissolved in DMF-DMA (20 mL),Add some 4A molecular sieves.The reaction mixture was stirred at 100C under nitrogen atmosphere for 15 hours.Cooled to room temperature and filtered to give crude solid (E)-2-(4-(dimethylamino)-2-oxo-3-butenyl)isoindoline-1,3-dione (600 mg) 47.5%).

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; BEIGENE, LTD; WANG, ZHIWEI; GUO, YUNHANG; (300 pag.)TWI602818; (2017); B;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

19155-24-9, name is 3,3-Dimethylindolin-2-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. Formula: C10H11NO

General procedure: To a solution of c1 ? c2 (1.0 equiv) and PIFA (1.2 equiv) in CH2Cl2 was stirred for 30 minutes at room temperature, then trifluoroacetate (10.0 equiv) was added to the mixture which was further stirred for 24 h at room temperature. Then, the reaction mixture was neutralized by sodium bicarbonate solution and extracted with ethyl acetate. The combined organic phases were dried and concentrated in vacuum and the residue was purified by silica gel chromatography (petroleum ether/ ethyl acetate = 1:1) to give d1 ? d2 (yield 50percent ? 60percent) as yellow solid.

The synthetic route of 19155-24-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Cheng, Kai; Li, Shiyu; Lv, Xiao; Tian, Yongbin; Kong, Haiyan; Huang, Xufeng; Duan, Yajun; Han, Jihong; Xie, Zhouling; Liao, Chenzhong; Bioorganic and Medicinal Chemistry Letters; vol. 29; 8; (2019); p. 1012 – 1018;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 3891-07-4, 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. 3891-07-4, name is 2-(2-Hydroxyethyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

N-(2-hydroxyethyl) phthalimide (100 g, 0.52 M) was coupled with 4-chloroethyl acetoacetate (50 g, 0.30 M) in the presence of sodium hydride in toluene under nitrogen atmosphere at ?11 to ?15 C. and at 25-30 C. for 12 hours and at 45 C. for 1 hour. The reaction mass was quenched in acidic water and extracted with toluene. The toluene extract was subjected to distillation and residue was degassed below 60 C.

The chemical industry reduces the impact on the environment during synthesis 2-(2-Hydroxyethyl)isoindoline-1,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Purohit, Arun Kumar; Desai, Brahmader Chilu; Shete, Balasaheb Dashrath; Bagwan, Salim Abbas; US2004/44218; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 1035235-27-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 1035235-27-8 name is tert-Butyl 4-bromoisoindoline-2-carboxylate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Example 136 r(S)-1-(2.4-Difluoro-3-phenoxy-phenyl)-propy|1-(2,3-dihydro-1 H-isoindol-4-yl)-am hydrochlorideStep 1 A solution of Key Intermediate 1 (50 mg, 0.19 mmol), fe -butyl 4- bromoisoindoline-2-carboxylate (57 mg, 0.19 mmol) and sodium fe -butoxide (26 mg, 0.27 mmol) in dioxane (1 ml) was degassed by bubbling through nitrogen for 5 mins. Tris(dibenzylideneacetone)dipalladium (0) (5 mg) and 2,2′-bis(diphenylphosphino)-1 ,1 ‘- binapthyl (5 mg) were added and the reaction mixture was heated to 120 C for 20 mins under microwave irradiation. The mixture was partitioned between sat. sodium hydrogen carbonate and ethyl acetate. The organic fractions were washed with brine, dried over magnesium sulfate, filtered and concentrated. The residue was purified by preparative hplc to give 4-[(S)-1-(2,4-difluoro-3-phenoxy-phenyl)-propylamino]-1 ,3-dihydro-isoindole-2- carboxylic acid tert-butyl ester (23 mg) as a solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl 4-bromoisoindoline-2-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; WOODHEAD, Andrew, James; CHESSARI, Gianni; BESONG, Gilbert, Ebai; CARR, Maria, Grazia; HISCOCK, Steven, Douglas; O’BRIEN, Michael, Alistair; REES, David, Charles; SAALAU-BETHELL, Susanne, Maria; WILLEMS, Hendrika, Maria, Gerarda; THOMPSON, Neil, Thomas; WO2013/64538; (2013); A1;,
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. 875003-43-3, name is 7-Fluoro-1-methylindoline-2,3-dione, A new synthetic method of this compound is introduced below., Formula: C9H6FNO2

Step 2: Preparation of 7-fluoro-1-methyl-1,3-dihydro-indol-2-one 7-Fluoro-1-methyl-1H-indole-2,3-dione (Step 1, 1.05 g, 5.86 mmol) is heated with neat hydrazine hydrate (10 ml) at 130 C. for 1 hour. The mixture is cooled, diluted with ice water and extracted with ethyl acetate. The extract is washed with brine, dried (Na2SO4), and evaporated to give the title compound as a light yellow solid. HPLC r.t. 4.07 min; MS for C9H8FNO m/z 165.16 (M+H)+.

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; Luehr, Gary W.; Jain, Rama; Renslo, Adam; Josyula, Vara Prasad Venkata Nagendra; Gordeev, Mikhail F.; US2006/30609; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 52351-75-4, name is 6-Methoxyindoline-2,3-dione, belongs to indolines-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 52351-75-4, Application In Synthesis of 6-Methoxyindoline-2,3-dione

Step 3: Preparation of 7-methoxy-2-phenyl-quinoline-4-carboxylic acid 112.Compound 111 (500 mg, 1 eq.) and acetophenone (380 muL, 1.2 eq.) were added at room temperature to a solution of KOH (520 mg, 3.3 eq.) in ethanol (5 mL). The reaction mixture was stirred at 70 0C for 7 hrs. The mixture was then poured into ice/water, and washed with dichloromethane. Aqueous layer was acidified with 3N HCl to pH 2-3. The precipitate obtained was filtered, washed with water, and triturated in ethanol to yield compound 112 as a beige solid in 40% yield. MS (ESI, EI+): m/z = 280 (MH+).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; IDENIX PHARMACEUTICALS, INC.; WO2009/14730; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 611-09-6, name is 5-Nitroindoline-2,3-dione, molecular formula is C8H4N2O4, 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. Product Details of 611-09-6

General procedure: A mixture of isatins 1a-f (1 mmol), active cyanomethanes 2a-b (1 mmol), and enolizable ketones 3a-d (1 mmol) in ethanol (3 ml)was stirred at room temperature in the presence of HIL (Scheme 2).The reaction progress was monitored by thin-layer chromatography (TLC). After completion of the reaction, the reaction mixture was treated with ethanol to recover the insoluble catalyst by filtration.The filtrate was then concentrated under vacuum and the desired product was obtained. The structures of the products were confirmed by 1H NMR, IR spectroscopy, and supported by elemental analysis. The filtered catalyst was dried under vacuum for 2 h and was reused with a fresh charge of solvent and reactants for subsequent runs under the same reaction conditions to observe its catalytic efficiency.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 611-09-6, its application will become more common.

Reference:
Article; Satasia, Shailesh P.; Kalaria, Piyush N.; Avalani, Jemin R.; Raval, Dipak K.; Tetrahedron; vol. 70; 35; (2014); p. 5763 – 5767;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 340702-10-5, A common heterocyclic compound, 340702-10-5, name is 6-Fluoroisoindolin-1-one, molecular formula is C8H6FNO, 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 stirred solution of 6-fluoroisoindolin-1-one (10 g, 66.2 mmol) in anhydrous dichloromethane (100 mL) were added triethylamine (16.72, 165.5 mmol, 21.8 mL), (Boc)2O (17.3 g, 79.4 mmol) and catalytic DMAP (100 mg) at room temperature. The reaction mixture was stirred at room temperature for 16 h. After completion, the reaction mixture was diluted with CH2Cl2, washed with H2O, and then saturated aqueous NaHCO3. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The crude compound was purified by silica gel chromatography (0-30% ethyl acetate in hexanes) to give the product. MS: (ES) m/z calculated for C13H14FNO3 [M+H]+ 252.3, found 252.3.

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; CHEMOCENTRYX, INC.; CHEN, Xi; DRAGOLI, Dean R.; FAN, Junfa; KALISIAK, Jaroslaw; LELETI, Manmohan Reddy; MALATHONG, Viengkham; McMahon, Jeffrey; TANAKA, Hiroko; YANG, Ju; YU, Chao; ZHANG, Penglie; Mali, Venkat; (62 pag.)US2017/144996; (2017); A1;,
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. 7477-63-6, name is 7-Chloroisatin, A new synthetic method of this compound is introduced below., Application In Synthesis of 7-Chloroisatin

The specific steps are:Add 7-chloroindole (54.5 mg, 0.3 mmol) to the pressure tube.Benzamidine hydrochloride (140.9 mg, 0.9 mmol),CuI (5.7 mg, 0.03 mmol)And potassium phosphate (381.6 mg, 1.8 mmol).Add 3mL of DMSO,After magnetic stirring at room temperature for 5 hours,The reaction solution was extracted with dichloromethane.The organic layer was washed with saturated brine.After drying anhydrous sodium sulfate,The solvent is distilled off under reduced pressure to obtain a crude product.The crude product is purified by column chromatography with dichloromethane/petroleum ether=1:20 (V/V) as the eluent to obtain the desired product. The product is a yellow solid.The yield was 68percent.

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; Wuhan Institute of Technology; Jia Fengcheng; Chen Yunfeng; (8 pag.)CN108558782; (2018); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 552330-86-6, These common heterocyclic compound, 552330-86-6, name is 5-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.

5-Bromo-2,3-dihydro-lH-isoindol-l-one (100 mg, 0.47 mmol) was dissolved in DMF (4.7 mL) and stirred at 0C. NaH (38 mg, 0.94 mmol, 60 wt.% dispersion in oil) was carefully added in two portions, and the resulting mixture was allowed to stir at 0C for 15 minutes before 2,2,2-trifluoroethyl trifluoromethanesulfonate (110 mg, 0.47 mmol) was added. The mixture was allowed to stir at 0C for 30 minutes before saturated aqueous NaHC03 (10 mL) was carefully added, and the mixture was extracted with EtOAc. The organic layer was washed with water, brine, dried over anhydrous MgS04, filtered, and concentrated in vacuo. The residue was purified by silica chromatography, eluting with a 0-20% EtOAc/hexanes gradient. LRMS (ESI) calc’d for Ci0H8BrF3NO [M+H]+: 294, found: 294.

Statistics shows that 5-Bromoisoindolin-1-one is playing an increasingly important role. we look forward to future research findings about 552330-86-6.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DINSMORE, Christopher; FULLER, Peter; GUERIN, David; THOMPSON, Christopher F.; PU, Qinglin; SCOTT, Mark E.; KATZ, Jason David; KURUKLASURIYA, Ravi; CLOSE, Joshua T.; FALCONE, Danielle; BRUBAKER, Jason; ZENG, Hongbo; BAI, Yunfeng; FU, Jianmin; KONG, Norman; LIU, Yumei; ZHENG, Zhixiang; WO2014/146492; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem