Month: June 2021

Related Products of 2058-74-4, These common heterocyclic compound, 2058-74-4, name is 1-Methylisatin, 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: The mixture of the Fe(III)(at)g-C3N4 nanocomposite (70 mg, 0.35 mmol based on Fe(III)) in aqueous media (3 ml) was dispersed for 30 min. Isatin (1 mmol) and indole (2.0 mmol) were added to the mixture and stirred in reflux conditions for an appropriate time. After the reaction was completed, the crude product was extracted with ethyl acetate and dried over anhydrous Na2SO4 followed by evaporation of the solvent. The pure products were achieved by recrystallization in hot ethanol and identified by IR, 1H & 13C NMR spectral data. The nanocomposite was washed with EtOH, dried, and reused for the next run.

Statistics shows that 1-Methylisatin is playing an increasingly important role. we look forward to future research findings about 2058-74-4.

Reference:
Article; Allahresani, Ali; Taheri, Bahare; Nasseri; Research on Chemical Intermediates; vol. 44; 11; (2018); p. 6741 – 6751;,
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., Formula: C9H9NO

Under nitrogen protection, 0.5 mmol of raw 5-methyl-2-indolinone, 1.2 mmol of pinacol borane and catalyst Y [N(SiMe3) 2] 30.05 mmol, 3 mL of toluene, reacted at 120 C for 36 h, and the product isolation yield was 87%.

According to the analysis of related databases, 3484-35-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wenzhou Medical University; Zhang Junfang; Cai Wenxuan; (11 pag.)CN110818608; (2020); A;,
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. 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C9H4F3NO3

Weigh5-trifluoromethoxy ruthenium0.95g (0.0041mol),0.85 g (0.0043 mol) of 4-chloroindole anhydride was added to a 100 ml three-necked flask containing a magnet, and then 40 ml of chloroform was added to the three-necked flask.1.5 ml of triethylamine, heated to reflux in an oil bath at 80 C for 3 h, after the reaction is over,The heating was stopped, and the mixture was cooled, and suction filtered to obtain a crude yellow solid powder.The product was washed 3 times with 10 ml of ethanol to obtain a pure product of a yellow solid powder.Dry and weigh 0.92g,The yield was 60.1%.

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 169037-23-4.

Reference:
Patent; Northwest University; Wang Cuiling; Bai Xiao; Zhang Xiaobin; Liu Jianli; (16 pag.)CN110143964; (2019); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 17564-64-6, 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. 17564-64-6, name is 2-(Chloromethyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

LiHMDS (37 mL of a 1 M solution in THF, 37.0 mmol) was added dropwise to a stirred solution of benzyl 2-methyl-4-oxo-piperidine-1-carboxylate (7.5 g, 30.3 mmol) in THF (150 mL) at -78 C under N2. After 50 minutes, a solution of 2-(chloromethyl)isoindoline-1,3- dione (8.0 g, 40.9 mmol) in THF (30 mL) was added to the reaction mixture over 5 minutes. The solution was stirred for 2 hours then quenched with a saturated aqueous NH4Cl solution. After warming to ambient temperature, the reaction mixture was diluted with EtOAc, washed with saturated aqueous sodium bicarbonate solution and brine. The organic phase was dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (silica, 0- 100% EtAOc/PE gradient elution) to give a mixture of benzyl 5-((1,3-dioxoisoindolin-2- yl)methyl)-2-methyl-4-oxopiperidine-1-carboxylate and benzyl 3-((1,3-dioxoisoindolin-2- yl)methyl)-2-methyl-4-oxopiperidine-1-carboxylate (2.4 g). This material was treated with DAST (8 mL, 61 mmol), with cooling in an ice bath. The resulting solution was stirred at 0 C for 15 minutes, then left to warm up to ambient temperature and stirred for 5 hours. The solution was poured carefully, dropwise, onto a stirred mixture of ice/water/NaHCO3/DCM. After 30 minutes, the organic phase was isolated and washed with brine. The organic was dried (Na2SO4), filtered and concentrated in vacuo. The crude mixture was purified by column chromatography (silica, 0- 100% EtOAc-PE gradient elution) give a colourless oil (1.5 g), of which 540 mg was dissolved in ethanol (15 mL) and hydrazine hydrate (100 muL, 2.0 mmol) added. The mixture was heated under relux for 3 hours then cooled to ambient temperature. The resulting suspension was filtered and the filtrate poured directly onto a pre-wetted ion-exchange cartridge. The cartridge was washed with methanol and the product eluted with a 2 M methanolic ammonia solution. The filtrate was concentrated under reduced pressure to give a pale yellow oil (300 mg). This material was dissolved in DCM (3 mL) and Et3N (200 muL, 1.4 mmol) was added under N2. The solution was cooled in an ice bath and methanesulfonyl chloride (100 muL, 1.3 mmol) added. After 5 minutes the cooling bath was removed and the mixture stirred at ambient temperature for 2 hours. The solution was diluted with DCM and saturated aqueous NaHCO3 solution. After stirring for 5 minutes, the organic phase was isolated using a phase separation cartridge. After concentration in vacuo, the residue was purified by column chromatography (silica, 0-100% [10% MeOH in EtOAc]-PE gradient elution) to give a pale yellow oil (150 mg). This material was taken up in DCM (3 mL) and Pd(OAc)2 (40 mg, 0.18 mmol), Et3SiH (150 muL, 0.94 mmol) and Et3N (100 muL, 0.72 mmol) were added. The reaction mixture was stirred at ambient temperature for 1 hour then diluted with MeOH. It was added onto a pre-wetted ion-exchange cartridge. The cartridge was washed with MeOH then the product eluted with a 2 M methanolic NH3 solution. The filtrate was concentrated under reduced pressure to give a brown oil (70 mg) containing a mixture of N-((4,4-difluoro-2- methylpiperidin-3-yl)methyl)methanesulfonamide A58 and N-((4,4-difluoro-6-methylpiperidin- 3-yl)methyl)methanesulfonamide A59, that was taken directly on to the next reaction; MS m/z: 234 (M+H)+.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2-(Chloromethyl)isoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK PATENT GMBH; VERTEX PHARMACEUTICALS INCORPORATED; BAYLY, Andrew; BLEICH, Matthew; CHARRIER, Jean-Damien; DODD, James; DURRANT, Steven; ENO, Meredith Suzanne; ETXEBARRIA I JARDI, Gorka; EVERITT, Simon; FRAYSSE, Damien; KELLY, Shazia; KNEGTEL, Ronald; MOCHALKIN, Igor; MORTIMORE, Michael; NORTH, Kiri; PORICHIS, Filippos; PULLIN, Robert; RUTHERFORD, Alistair; STORCK, Pierre-Henri; TWIN, Heather Clare; XIAO, Yufang; (1159 pag.)WO2019/148132; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 169037-23-4, These common heterocyclic compound, 169037-23-4, name is 5-(Trifluoromethoxy)indoline-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.

Weigh out 0.35 g (0.0015 mol) of 5-trifluoromethoxy ruthenium,0.39 g (0.0016 mol) of 5-bromoanthoic anhydride was added to a 100 ml three-necked flask containing a magnet, and then 40 ml of chloroform was added to the three-necked flask.1.5 ml of triethylamine, heated to reflux in an oil bath at 80 C for 3 h, after the reaction is over,The heating was stopped, and the mixture was cooled, and suction filtered to obtain a crude yellow solid powder.The product was washed 3 times with 10 ml of ethanol to obtain a pure product of a yellow solid powder.It was dried and weighed 0.45 g, and the yield was 72.6%

Statistics shows that 5-(Trifluoromethoxy)indoline-2,3-dione is playing an increasingly important role. we look forward to future research findings about 169037-23-4.

Reference:
Patent; Northwest University; Wang Cuiling; Bai Xiao; Zhang Xiaobin; Liu Jianli; (16 pag.)CN110143964; (2019); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 71294-03-6,Some common heterocyclic compound, 71294-03-6, name is 7-Fluoroindolin-2-one, molecular formula is C8H6FNO, 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.

Step 1a: Preparation of 7-fluoro-1-methyl-1,3-dihydro-indol-2-one (7) This is similar to the procedure described in G. W. Rewcastle, B. D. Palmer, E. M. Dobrusin, D. W. Fry, A. J. Kracker and W. A. Deny, Journal of Medicinal Chemistry, 1994, 37, 2033-2042. A suspension of the 7-fluoro-1,3-dihydro-indol-2-one (9, 1.0 g, 6.62 mmol.) in H2O (30 mL) and NaOH (0.397 g, 9.92 mmol., 1.50 eq.) was treated with dimethyl sulfate (1.24 g, 9.86 mmol., 1.49 eq., 0.933 mL; added all at once) and heated to 100 C. for approx. 10 min. and then allowed to cooled to about 50 C. An additional 1.0 eq. of NaOH (0.265 g) and then additional 1 eq. of dimethyl sulfate (0.835 g, 0.626 mL) were added. Again heated to 100 for approx. 10 min. Then cooled to 0 C. in an ice bath and stirred and then filtered off solids, washed several times with water and dried on buchner funnel under vacuum overnight to yield the title compound as a solid. 1H NMR (400 MHz, CHLOROFORM-D) delta ppm 3.4 (d, J=2.5 Hz, 3H) 3.5 (s, 2H) 6.9 (m, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7-Fluoroindolin-2-one, its application will become more common.

Reference:
Patent; Josyula, Vara Prasad Venkata Nagendra; Gordeev, Mikhail; Luehr, Gary; US2006/229349; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 99365-40-9, name is 6-Bromoindolin-2-one, 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 99365-40-9, Formula: C8H6BrNO

a) 6′-Bromospirorcyclopropane-l,3′-indolinl-2′-one A solution of 6-bromoindolin-2-one (2 g, 9.43 mmol) and diisopropylamine (2.00 g, 2.82 ml, 19.8 mmol) in tetrahydrofuran (16 ml) was cooled to -25C and a solution of nBuLi (1.6 M in hexane, 23.6 ml, 37.7 mmol) was added dropwise. The reaction mixture was warmed to 0C and a solution of 1,2-dibromoethane (5.32 g, 2.44 ml, 28.3 mmol) in tetrahydrofuran (2 ml) was added dropwise. The reaction mixture was warmed to room temperature, stirred for 20 hours and carefully quenched with brine (2 ml) and cone. HC1 (2 ml, ice bath). The reaction mixture was diluted with tert-butyl methyl ether and water. The aqueous phase was extracted with tert-butyl methyl ether, the combined organic phases were washed with brine and dried over sodium sulfate. The solvent was evaporated and the residue purified by silica gel chromatography using ethyl acetate/ heptane as eluent. The title compound was obtained as red crystals (1.11 g). MS ESI (m/z): 238.3/ 240.3 [(M+H)+]. 1H NMR (DMSO-D6, 400 MHz): (ppm) = 10.67 (bs, IH), 7.12-7.09 (m, IH), 7.03 (m, IH), 6.95-6.92 (m, IH), 1.61-1.57 (m, 2H), 1.49-1.45 (m, 2H).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 6-Bromoindolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BRUNNER, Daniela; MALBERG, Jessica; SHANKAR, Bavani G.; KOLCZEWSKI, Sabine; LIMBERG, Anja; PRINSSEN, Eric; RIEMER, Claus; STOLL, Theodor; WO2014/40969; (2014); 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. 5394-18-3, name is 2-(4-Bromobutyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Formula: C12H12BrNO2

General procedure: For the synthesis of compounds 6a-d we used commercially available (from Sigma Aldrich) N-(bromoalkyl)isoindoline-1,3-diones. To the solution of N-(bromoethyl)isoindoline-1,3-dione (3.93 mmol) in DMF, sodium azide (11.79 mmol) was added and the contents were heated at 80 C for 6-8 h. After completion, reaction mixture was quenched with ice water and extracted with DCM thrice. The organic extracts were combined, dried over anhydrous sodium suphate, filtered, and concentrated under reduced pressure to give corresponding products as colorless oil and was used without further purification

The synthetic route of 5394-18-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kushwaha, Khushbu; Kaushik, Nagendra; Lata; Jain, Subhash C.; Bioorganic and Medicinal Chemistry Letters; vol. 24; 7; (2014); p. 1795 – 1801;,
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. 20780-72-7, name is 4-Bromoisatin, A new synthetic method of this compound is introduced below., Product Details of 20780-72-7

General Procedure 3 Suzuki Coupling of 4-bromoindoline-2,3-dione Derivatives with Trifluoroborate Potassium Salts [0344] 4-Bromoisatin (1 eq) was added to a solution of the potassium trifluoroborate salt (1.4 eq), K3PO4 (3.6 eq) and degassed solvent. The reaction mixture was degassed and Pd(PPh3)2Cl2 or Pd(dppf)2Cl2 (0.1 eq) was added. The reaction vessel was sealed and heated by microwave irradiation (Biotage Initiator) for 4 h at 130° C. The reaction mixture was cooled to rt, diluted with EtOAc (10 mL/mmol substrate) and filtered through Celite®. The organic solution was washed with brine (10 mL/mmol substrate) and the resulting aqueous layer was further extracted with EtOAc (2×). The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo to give the crude product which was purified as specified below. Example 51-preparation of 2?-(((9-Cyclopropyl-5H-[1,2,4]triazino[5,6-b]indol-3-yl)thio)methyl)benzonitrile 4-Cyclopropylindoline-2,3-dione Following General Procedure 3,4-bromoisatin (300 mg, 1.33 mmol), potassium cyclopropyltrifluoroborate (275 mg, 1.86 mmol), K3PO4 (1.01 g, 14.8 mmol) and Pd(dppf)2Cl2 (93 mg, 0.13 mmol) in THF/ H2O (3:1, 4 mL) gave the crude reaction mixture, which was purified via flash column chromatography (eluent 30-40° C. petrol/acetone, 4:1) to afford the product as an orange solid. (36 mg, 43percent). [0645] deltaH (500 MHz, DMSO-d6); 0.80-0.84 (2H, m), 1.06-1.15 (2H, m), 2.78-2.89 (1H, m), 6.49 (1H, d, J=7.8 Hz), 6.62 (1H, d, J=7.8 Hz), 7.40 (1H, app t, J=7.8 Hz), 10.98 (1H, br s) [0646] deltaC (125 MHz, DMSO-d6) 10.6, 10.9, 108.4, 116.8, 126.3, 138.2, 147.6, 150.4, 159.2, 176.7 [0647] mp 145-148° C.

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; Christou, Ivy; Cross, Rebecca Lillian; Gianella-Borradori, Matteo; Greaves, David Robert; Russell, Angela Jane; Wynne, Graham Michael; US2014/378451; (2014); 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. 496-12-8, name is Isoindoline, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: Isoindoline

To the suspension of isoindoline (2 g, 16.8 mmol) in 98% H2SO4 (10 mL) was added dropwise the mixture of concentrated nitric acid (2 mL) and 98% sulfuric acid (2 mL) at 0C. The mixture was stirred at 0C for 45 minutes. The resulting yellow solution was then poured into ice water. The white solid precipitate was collected by filtration. The solid was washed with water (20 mL x 2) and dried in vacuum to afford 231a as a white solid (700 mg, 51%). MS: [M+H]+ 165.

According to the analysis of related databases, 496-12-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GILEAD CONNECTICUT, INC.; GENENTECH, INC.; BARBOSA, Antonio, J., M.; BLOMGREN, Peter, A.; CURRIE, Kevin, S.; KRISHNAMOORTHY, Ravi; KROPF, Jeffrey, E.; LEE, Seung H.; MITCHELL, Scott A.; ORTWINE, Daniel; SCHMITT, Aaron, C.; WANG, Xiaojing; XU, Jianjun; YOUNG, Wendy; ZHANG, Honglu; ZHAO, Zhongdong; ZHICHKIN, Pavel E.; WO2011/140488; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem