Month: February 2021

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. 3484-35-3, name is 5-Methylindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 3484-35-3

General procedure: The mixture of oxindole 1 (0.1 mmol), beta,gamma-unsaturated alpha-keto ester 2 (0.12 mmol),DABCO (0.02 mmol) in 1 mL H2O were stirred at room temperature. After stirringfor the indicated time, the mixture was extracted with ethyl acetate. The combinedorganic phase was dried over Na2SO4 and concentrated in vacuo. The residue wasfurther purified by washing with PE/EA to afford the desired products.

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

Reference:
Article; Han, Man-Yi; Pan, Ping; Sheng, Fei-Fei; Synlett; vol. 28; 11; (2017); p. 1378 – 1382;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

954-81-4, name is N-(5-Bromopentyl)phthalimide, 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. Product Details of 954-81-4

General procedure: 2-(omega-Bromoalkyl)-isoindoline-1,3-dione (1 equiv) with N-methylbenzylamine (1 equiv) or its substituted analog in the presence of K2CO3 (3 equiv) was stirred in acetonitrile under reflux for 16 h. Once the reaction was finished, the solvent was evaporated under vacuum, producing a residue that was further dissolved in 50 mL of 5 M NaOH and extracted with ethyl acetate (3 x 50 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (dichloromethane to dichloromethane/methanol 98:2), yielding a yellow oil. The final product was obtained in the form of hydrochloride salt. The following compounds were obtained.

The synthetic route of 954-81-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Guzior, Natalia; Bajda, Marek; Rakoczy, Jurand; Brus, Boris; Gobec, Stanislav; Malawska, Barbara; Bioorganic and Medicinal Chemistry; vol. 23; 7; (2015); p. 1629 – 1637;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 6780-38-7,Some common heterocyclic compound, 6780-38-7, name is 2-(1,3-Dioxoisoindolin-2-yl)acetyl chloride, molecular formula is C10H6ClNO3, 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 Boc-hydrazine (7.08. g, 53.5 mmol) in DCM (200 mL) was added Et3N (13.5 mL, 97.4 mmol) , and then compound 651 (10.8 g, 48.7 mmol) was added at 0 . After that the reaction was stirred at r.t. for 30 min. and poured into ice-water (100 mL) and extracted with DCM (3 ¡Á 100 mL) . The combined organic phases were washed with water (100 mL) and brine (100 mL) , dried over anhydrous Na2SO4, filtered and concentrated to give a white solid (15.5 g, 100%yield) . ESI m/z calcd for C15H18N3O5[M+H]+: 320.12, found: 320.12.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(1,3-Dioxoisoindolin-2-yl)acetyl chloride, its application will become more common.

Reference:
Patent; HANGZHOU DAC BIOTECH CO. LTD; ZHAO, Robert Yongxin; YANG, Qingliang; HUANG, Yuanyuan; ZHAO, Linyao; GAI, Shun; YE, Hangbo; LEI, Jun; XU, Yifang; CAO, Mingjun; GUO, Huihui; JIA, Junxiang; TONG, Qianqian; LI, Wenjun; ZHOU, Xiaomai; XIE, Hongsheng; BAI, Lu; CAI, Xiang; ZHUO, Xiaotao; ZHANG, Xiuzheng; ZHENG, Jun; (424 pag.)WO2019/127607; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 19727-83-4, 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. 19727-83-4 name is 6-Nitroindoline, 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.

1-(6-Nitroindolin-1-yl)-acetonitrile A stirred mixture of 6-nitroindoline (2.0 g, 12 mmol), potassium carbonate (3.36 g, 24 mmol), sodium iodide (3.65 g, 24.4 mmol), acetone (20 mL) and chloroacetonitrile (1.5 mL, 24 mmol) was heated under reflux for 16 h. The mixture was cooled to room temperature, filtered and the filter-cake washed with ethyl acetate. The filtrate was concentrated in vacuo and purified by column chromatography [SiO2; heptane-ethyl acetate (9:1)] to give the product (1.3 g, 53% yield) as a pale yellow solid: IR numax (Nujol)/cm-1 1615, 1513, 1487, 1343, 1293, 1145, 804 and 739; NMR deltaH (400 MHz, CDCl3) 3.11 (2H, t, J 7.5 Hz), 3.59 (2H, t, J 7.5 Hz), 4.14 (2H, s), 7.19-7.23 (1H, m), 7.31-7.33 (1H, m) and 7.69-7.72 (1H, m).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Nitroindoline, and friends who are interested can also refer to it.

Reference:
Patent; Vernalis Research Limited; US6380238; (2002); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 603-62-3, These common heterocyclic compound, 603-62-3, name is 3-Nitrophthalimide, 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 appropriate thiol (6 mmol), 3-nitrophthalimide(4 mmol) and K2CO3 (10 mmol) in 20 mL acetone was heated underreflux for 24 h. The reaction was cooled to room temperature anddiluted with 150 mL water. The mixture was subsequently acidifiedto pH 2 with 6 N HCl. The resulting precipitate was collectedby filtration and dried at 50 C [19].

The synthetic route of 603-62-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Van Der Walt, Mietha M.; Terre’Blanche, Gisella; Petzer, Anel; Petzer, Jacobus P.; Bioorganic Chemistry; vol. 59; (2015); p. 117 – 123;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, 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 102359-00-2, name: 2-Oxoindoline-5-carboxylic Acid

General procedure: Aldehydes (1-5) (0.2 mmol) and oxindoles (7-11) (0.2 mmol) were dissolved in alcohol MeOH, EtOH, or tert-BuOH (1.5 ml). 3 droplets of piperidine were added to the solvents and the reaction mixture was stirred in a sealed vial at 60 – 70 C for 2 – 8 hours.

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:
Article; Nemes, Zoltan; Takacs-Novak, Krisztina; Voelgyi, Gergely; Valko, Klara; Beni, Szabolcs; Horvath, Zoltan; Szokol, Balint; Breza, Nora; Dobos, Judit; Szantai-Kis, Csaba; Illyes, Eszter; Boros, Sandor; Kok, Robbert Jan; ?rfi, Laszlo; Bioorganic and Medicinal Chemistry Letters; vol. 28; 14; (2018); p. 2391 – 2398;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 17564-64-6, A common heterocyclic compound, 17564-64-6, name is 2-(Chloromethyl)isoindoline-1,3-dione, molecular formula is C9H6ClNO2, 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.

LiHMDS (5 mL of 1M solution, 5.0 mmol) was added dropwise to a solution of benzyl 3-ethyl-4-oxo-piperidine-1-carboxylate (1 g, 3.8 mmol) in THF (14 mL) cooled to -78 C under N2.90 minutes later, a solution of 2-(chloromethyl)isoindoline-1,3-dione (1.0 g, 5.1 mmol) in THF (2 mL) was added. The solution was stirred at -78 C for 1 hour then at 0 C for 1 hour, then quenched by adding saturated aqueous NH4Cl solution (~2 mL). The reaction mixture was diluted with EtOAc, washed with a saturated aqueous sodium bicarbonate solution and brine. The organic phase was dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (silica, PE/EtOAc gradient elution) to give benzyl 3-[(1,3- dioxoisoindolin-2-yl)methyl]-5-ethyl-4-oxo-piperidine-1-carboxylate as a colourless gum (1.1 g), which was taken directly on to the next step; MS m/z: 421 (M+H)+.

The synthetic route of 17564-64-6 has been constantly updated, and we look forward to future research findings.

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

These common heterocyclic compound, 16800-68-3, name is 1-Acetylindolin-3-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. Formula: C10H9NO2

General procedure: To a solution of 1a (35 mg, 0.2 mmol) and 2a (52.4 mg,0.4 mmol) in DCE (3 mL) was added iodine (10 mg, 0.04 mmol). The reaction mixture was heated at 80 C for 24 h, then cooled to room temperature and quenched with saturated sodium thiosulfate. The mixture was extracted with CH2Cl2, the combined organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel to afford title compound.

The synthetic route of 1-Acetylindolin-3-one has been constantly updated, and we look forward to future research findings.

Reference:
Article; Guo, Jing; Weng, Jiang; Huang, Gong-Bin; Huang, Lin-Jie; Chan, Albert S.C.; Lu, Gui; Tetrahedron Letters; vol. 57; 49; (2016); p. 5493 – 5496;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 1127-59-9, name is 7-Methylindoline-2,3-dione, molecular formula is C9H7NO2, 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. COA of Formula: C9H7NO2

General procedure: To an ethanolic solution of triazole-hydrazide 5 (1.0mmol) was added equimolar amount of substituted Isatin (8a-i) and refluxed overnight at 80C. After completion of the reaction, crude obtained was filtered, washed with water to get Isatin-triazole hydrazones (9a-i) which was purified by column chromatography eluted with acetone: DCM (1:9) to afford the title compounds in moderate to good yield [53].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1127-59-9, its application will become more common.

Reference:
Article; Aneja, Babita; Khan, Nashrah Sharif; Khan, Parvez; Queen, Aarfa; Hussain, Afzal; Rehman, Md. Tabish; Alajmi, Mohamed F.; El-Seedi, Hesham R.; Ali, Sher; Hassan, Md. Imtaiyaz; Abid, Mohammad; European Journal of Medicinal Chemistry; vol. 163; (2019); p. 840 – 852;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 19155-24-9, 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. 19155-24-9 name is 3,3-Dimethylindolin-2-one, 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.

22c. 3,3-dimethylindoline To a solution of 22b (1.0 g, 6.2 mmol) in THF at 0¡ã C. was added LiAlH4 (1M THF solution, 13.6 mL, 2.2 eq) under nitrogen. The resulting slurry was heated at reflux for 4 h. While cooling in an ice bath, sat’d Na2SO4 was added carefully to quench the extra un-reacted LiAlH4. The solids were filtered out, and were rinsed with EtOAc. The organic was washed with H2O, brine, dried over MgSO4, filtered, and concentrated to dryness to give almost pure 22c (0.82 g, yield: 89percent). LC-MS ESI 148 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,3-Dimethylindolin-2-one, and friends who are interested can also refer to it.

Reference:
Patent; Tuerdi, Huji; Chao, Hannguang J.; Qiao, Jennifer X.; Wang, Tammy C.; Gungor, Timur; US2005/261244; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem