Month: January 2021

496-12-8, name is Isoindoline, 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. category: indolines-derivatives

General procedure: A mixture of the amine (2.0 mmol), EDC (2.6 mmol), and HOBt (3.3 mmol) were purged with nitrogen before the addition of the acid (2.6 mmol) and THF (10 ml). DIPEA (11.0 mmol) was then added and the reaction was stirred at room temperature for 16 h. The reaction mixture was poured into a separatory funnel containing saturated NH4Cl (10 ml) and extracted with ethyl acetate (3 ¡Á 30 ml). The combined organic layers were dried over Na2SO4, concentrated under vacuum. Purification on silica gel yielded the desired product.

The synthetic route of 496-12-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Awuah, Emelia; Ma, Eric; Hoegl, Annabelle; Vong, Kenward; Habib, Eric; Auclair, Karine; Bioorganic and Medicinal Chemistry; vol. 22; 12; (2014); p. 3083 – 3090;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6326-79-0, name is 6-Bromoisatin, 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 6326-79-0, Application In Synthesis of 6-Bromoisatin

General procedure: Isatins I (3.0 mmol) was dissolved in anhydrous DMF (15 mL), and the resultant solution was cooled to 0 C (ice bath), whereupon sodium hydride (60% dispersion in mineral oil, 140mg, 3.5 mmol, 1.17 equiv) was added in one portion and stirred for 5 minutes. Iodomethane (497 mg, 3.5 mmol, 1.17 equiv) or benzyl bromide (564.3 mg, 3.3 mmol, 1.1 equiv) was added and the reaction was stirred at 0 C for 30min. The reaction was monitored by TLC until I was fully consumed. The reaction mixture was then poured into saturated aqueous NH4Cl and extracted with ethyl acetate. The combined organic portions were washed with water and brine, dried (MgSO4), filtered, and concentrated to give N-methyl isatins and N-benzyl isatins II (90%-100% yield).

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; Liang, Jin-Yan; Wang, Hui; Yang, Yan-Li; Shen, Shou-Jie; Chen, Jian-Xin; Tetrahedron Letters; vol. 58; 27; (2017); p. 2636 – 2639;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 334952-09-9, 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. 334952-09-9, name is 2-Oxoindoline-6-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows.

2-carbonylindolone-6-carboxylic acid (40 g, 0.23 mol) was added to the reaction flask, 200 ml of methanol was added, and the mixture was slowly added dropwise, and the temperature was raised to 60 C by slowly dropping thionyl chloride (32 g, 0.27 mol). The reaction was carried out for 6 hours. After completion of the reaction, the reaction mixture was evaporated to dryness, ground with methanol, filtered and dried to obtain 40 g of 2-carbonylindolone-6-carboxylate in a yield of 93%.

The chemical industry reduces the impact on the environment during synthesis 2-Oxoindoline-6-carboxylic acid. I believe this compound will play a more active role in future production and life.

Reference:
Patent; (6 pag.)CN106854173; (2017); 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.

General procedure: Bromoisoindolin-1-one (2.0 g, 9.43 mmol) was dissolved with warming in DMF (150 mL),then cooled to 0C. NaH (415 mg, 10.4 mmol) was added and the mixture stirred under N2 at 0C for 0.5 h. Methyl iodide (0.65 mL, 10.4 mmol) was added dropwise and the reaction allowed to warm to room temperature and stir for another I h. A small quantity of water was added to quench the reaction then the DMF removed under reduced pressure to give an oily yellow residue which was dissolved in EtOAc (150 mL). This solution waswashed with water (3×100 mL), brine (100 mL) and dried (Na2SO4)., Removal of the solvent under reduced pressure gave a solid which was purified by filtration through a plug of silica gel (10% acetone/CH2C12 as eluant). The title compound was isolated as a very pale yellow crystalline solid (1.64 g, 80%). ? H NMR [400 MHz, (CD3)2S0] oe 7.85 (dd, J= 1.5, 0.6 Hz, 1 H), 7.66 (dd, J= 8.0, 1.7 Hz, 1 H), 7.59 (d, J- 8.0 Hz, I H), 4.46 (s,2 H), 3.05 (s, 3 H). LRMS (APCI) calcd for C9H8BrNO 226, 228 (MH), found 226, 228.

The synthetic route of 552330-86-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PETER MACCALLUM CANCER INSTITUTE; SPICER, Julie Ann; DENNY, William Alexander; MILLER, Christian Karl; O’CONNOR, Patrick David; HUTTUNEN, Kristiina; TRAPANI, Joseph A.; HILL, Geoff; ALEXANDER, Kylie; WO2014/28968; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 6941-75-9, The chemical industry reduces the impact on the environment during synthesis 6941-75-9, name is 5-Bromoisoindoline-1,3-dione, I believe this compound will play a more active role in future production and life.

280 ml of 1 M Borane-THF complex was added dropwise to a stirred solution of 4-bromophthalimide (20.85 g; 92.2 mmol) in anhydrous THF (200 ml) at O0C then heated at reflux overnight. The reaction was cooled to 00C then treated cautiously with methanol (100 ml) followed by 2M HCI (100 ml) then heated at reflux for 3 hours. The reaction mixture was cooled and the organics evaporated. The aqueous was diluted with water (100 ml) the extracted with DCM (x3). The aqueous was basified with 2M NaOH then extracted with DCM (x3). The combined DCM extracts were dried (MgSO4), filtered and evaporated to give 6.99 g of 5-bromo-2,3-dihydro-1 H-isoindole as a dark brown gummy solid. 1H NMR (DMSO-d6) 7.45 (1 H, s), 7.36 (1H, d), 7.20 (1 H, d), 4.05 (4H, s).

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, 5-Bromoisoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; WO2008/44045; (2008); 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. 32692-19-6, name is 5-Nitroindoline, This compound has unique chemical properties. The synthetic route is as follows., Formula: C8H8N2O2

General procedure: To a stirred solution of aryl halides (1.0 mmol) and indoline/indoline carboxylic acid (1.0 equiv) in dry DMSO (2.0 mL) at rt was added nano CuO (5.0 mol %) followed by Cs2CO3 (2.0 equiv) and heated at 80 C for 8 h. The progress of the reaction was monitored by TLC. After the reaction was complete, the reaction mixture was cooled to room temperature and catalyst was filtered, the crude residue was extracted with ethyl acetate (3 ¡Á 10 mL). The combined organic layers were extracted with water, saturated brine solution, and dried over anhydrous Na2SO4. The organic layers were evaporated under reduced pressure and the resulting crude product was purified by column chromatography by using ethyl acetate/hexane (7:3) as eluent to give the corresponding N-substituted indoles in excellent yields. The identity and purity of the product were confirmed by 1H, 13C NMR, and mass spectra.

According to the analysis of related databases, 32692-19-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Reddy, K. Harsha Vardhan; Satish; Ramesh; Karnakar; Nageswar; Tetrahedron Letters; vol. 53; 24; (2012); p. 3061 – 3065;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 1914-02-9, The chemical industry reduces the impact on the environment during synthesis 1914-02-9, name is 3,3-Dimethylindoline, I believe this compound will play a more active role in future production and life.

To a solution of l-((tert-butoxycarbonyl)amino)cyclopropanecarboxylic acid (155 mg, 0.770 mmol) in 7 mL DMF, triethylamine (130 mu,, 0.933 mmol) and HATU (325 mg, 0.855 mmol) were added. After stirring at room temperature for 5 min, 3,3-dimethylindoline (105 mg, 0.713 mmol) was added. After stirring at room temperature for overnight, the mixture was extracted with AcOEt and brine. Organic phase was dried over MgS04, filtered, and concentrated. The residue was purified by silica gel column chromatography to give tert-butyl (l-(3,3-dimethylindoline-l- carbonyl)cyclopropyl)carbamate (215 mg) as a white solid. LCMS m/z = 331.2 [M+l]+; NMR (400 MHz, CDC13) delta ppm 1.02-1.15 (m, 2H), 1.33 (s, 6H), 1.40 (s, 9H), 1.54-1.57 (m, 2H), 4.03 (s, 2H), 7.03-7.05 (m, 1H), 7.13-7.15 (m, 1H), 7.18-7.22 (m, 1H), 7.92-7.93 (m, 1H).

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, 3,3-Dimethylindoline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; SEMPLE, Graeme; BEHAN, Dominic P.; FEICHTINGER, Konrad; GLICKLICH, Alan; GROTTICK, Andrew J.; KAM, Maria Matilde Sanchez; KASEM, Michelle; LEHMANN, Juerg; REN, Albert S.; SCHRADER, Thomas O.; SHANAHAN, William R.; WONG, Amy Siu-Ting; ZHU, Xiuwen; WO2015/66344; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 1127-59-9, 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. 1127-59-9, name is 7-Methylindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Mg(ClO4)2 (0.1 g) was added to a mixture of isatin (2 mmol), and dimedone (4 mmol) in aqueousethanol solution (50percent, v/v, 5 mL), and the resulting mixture was stirred at 80¡ãC for 10?12 h. Upon completion of the reaction (TLC, Ethyl acetate/Petroleum ether = 1:4), the mixture was allowedto cool to room temperature. The resulting solid was filtered and washed successively with water(2 30 mL) and cold aqueous ethanol (2 1 mL) to afford a crude product, which was recrystallizedfrom EtOH to afford the pure product 3. Some insolubility could be observed in the refluxing ethanolduring the recrystallization process, which should be filtered when hot.

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, 7-Methylindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Chen, Chunfeng; Lv, Chunlei; Liang, Jianfeng; Jin, Jianqing; Wang, Lijun; Wu, Chunlei; Shen, Runpu; Molecules; vol. 22; 8; (2017);,
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. 264916-06-5, name is tert-Butyl 5-aminoisoindoline-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., category: indolines-derivatives

A solution of 2-Boc-5-aminoisoidoline (50mg, 0.21 inmol) and paraformaldehyde (64 nip, 2.1 mmol) in MeOH (1 mL) and HOAc (1 mL) was treated with NaCNBH3 (72 mg, 1.05 mmol) . The reaction was allowed to proceed for 6 hours, after which the mixture was diluted with water (about 20 mL) . The pH value was adjusted to about 12 by the addition of concentrated aq. NaOh before the solution was extracted with CH2C12. The organic extracts were combined and dried over Na2SO4. Following removal of the solvent, the product was purified by flash chromatography (Si02, 20% EtOAc/hexanes) . Yield: 35.6 mg (65%), pale yellow oil, mixture of rotamers. 1H NMR (400 MHz, ODd3) 7.13 and 7.08 (d, J = 8.4 Hz, 1H), 6.82 – 6.46 (m, 2H) , 4.77 – 4.45 (m, 4H) , 3.06 – 2.85 (m, 6H), 1.51 (s, 9H) . 3g NMR (151 MHz, CDC13) 5 154.2,154.1, 150.0, 138.0, 137.6, 122.7, 122.4, 111.9,106.1, 79.0, 52.2, 51.8, 51.3, 51.0, 40.6, 28.1. HRESI-TOF m/z 263.1755 (C15H22N202 + H, required 263.1754)

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 264916-06-5.

Reference:
Patent; THE SCRIPPS RESEARCH INSTITUTE; BOGER, Dale, L.; (104 pag.)WO2017/210206; (2017); A1;,
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. 110568-64-4, name is 6-Nitroisoindolin-1-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Safety of 6-Nitroisoindolin-1-one

Toa solution of7D (35 g, 0.2 mol) in MeOH(350 mL) was added Pd/C (7 g), the mixture was stirred at 50C underH2 at 50 psi for 2 hr.Themixturewas filtered and concentratedin vacuumto afford crude7E (30g) as a white solid.

The synthetic route of 110568-64-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAIKANG (SUZHOU) CO., LTD; HAN, Jie; WO2015/81891; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem