Category: indolines-derivatives

Synthetic Route of 2913-97-5, 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. 2913-97-5, name is N-(2-Oxoethyl)phthalimide belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a stirred solution of 2-(l,3-dioxoisoindolin-2-yl)acetaldehyde (product of step-3, 4.0 g, 21.15 mmol) in ethanol (40 mL), added hydroxylamine hydrochloride (2.930 g, 42.305 mmol) followed by sodium bicarbonate (3.55 g, 42.305 mmol) at room temperature and stirred at room temperature for 16 h. The solvent was stripped off, added water (50 mL) and extracted with ethyl acetate (2 x 100 mL). The combined organic layer was washed with water (100 mL) followed by brine, dried over sodium sulphate and concentrated under vacuum to get the title compound (3.2 g, 74percent) as an off white solid. LCMS: m/z 204.1 [M+H] +; NMR (300 MHz, DMSO-d6) delta 11.36 (s, 1H), 7.98 – 7.78 (m, 4H), 6.83 (t, / = 3.8 Hz, 1H), 4.39 (dd, / = 3.9, 0.9 Hz, 2H).

The synthetic route of N-(2-Oxoethyl)phthalimide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; CHIKKANNA, Dinesh; KHAIRNAR, Vinayak; (74 pag.)WO2016/12958; (2016); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 18711-13-2, name is 4,7-Dichloroindoline-2,3-dione, molecular formula is C8H3Cl2NO2, 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. Safety of 4,7-Dichloroindoline-2,3-dione

General procedure: A mixture of isatin derivative (1.0 mmol), trans-4-hydroxy-L-proline (0.131 g,1 mmol), and CTAB (4 mmol) in water (50mL) was stirred at 80 C for 30 min. After completion of the reaction (monitored by TLC), the contents were filtered and the residue was washed thoroughly with water until free from CTAB. Finally, the residue was crystallized from a chloroform-petroleum ether mixture to afford the desired products in excellent yields. The characterizations of the products were accomplished by spectroscopic analysis (1H, 13C NMR, FTIR, and ESI-mass) and also by comparison of the data reported in the literature.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 18711-13-2, its application will become more common.

Reference:
Article; Naskar, Subhendu; Roy, Suprakash; Sarkar, Swarbhanu; Synthetic Communications; vol. 44; 11; (2014); p. 1629 – 1634;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 56341-37-8, name is 6-Chlorooxindole, 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 56341-37-8, Recommanded Product: 6-Chlorooxindole

Example 37 Preparation of intermediate E/Z-3-[5-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-pentylidene]-6-chloro-1,3-dihydro-indol-2-one To the mixture of 6-chlorooxindole (3.3 g, 20 mmol) (Crescent) and 5-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-pentanal (6.5 g, 26.6 mmol) in methanol (150 mL) was added a methanolic solution (25%, Aldrich) of sodium methoxide (10 g, 46 mmol) dropwise. The reaction mixture was stirred at room temperature for 10 min. The solvent was removed, and the residue was partitioned between ethyl acetate and water. The organic layer was separated, dried over Na2SO4, and concentrated. The residue was purified by chromatography (25-33% EtOAc in hexanes) to give E/Z-3-[5-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-pentylidene]-6-chloro-1,3-dihydro-indol-2-one as a off white solid (Yield 3.6 g, 46%).

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

Reference:
Patent; Liu, Jin-Jun; Zhang, Jing; Zhang, Zhuming; US2011/201635; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 17702-83-9, 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. 17702-83-9, name is 2-(8-Bromooctyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

a) Preparation of 8-piperidinyloctylphthalimide 8-Bromooctylphthalimide (517 mg; 2.0 mmoles) and piperazine (0.40 ml; 4.0 mmoles) were dissolved in anhydrous ethyl ether (5 ml). Reaction times and process as per Example 1. 431 mg of pure product were obtained. Yield 63percent.

The synthetic route of 2-(8-Bromooctyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEDIOLANUM FARMACEUTICI S.P.A.; EP575954; (1993); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 20780-72-7, 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. 20780-72-7 name is 4-Bromoisatin, 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.

General procedure: A mixture of 1 (0.4 mmol), 2 (0.4 mmol), Na2CO3 (0.8 mmol) and TBHP (0.4 mmol) in DMF (4 mL) was stirred at rt for 2 h. Then, the mixture was poured into ice-water, acidified with 1 N HCl aq. (6 mL). The mixture was extracted with ethyl acetate (20 mL x 3). The combined organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by silica gel flash column chromatography to give desired products.

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

Reference:
Article; Wu, Jun; Zhang, Hui; Ding, Xiao; Tan, Xuefei; Shen, Hong C.; Chen, Jie; He, Weimin; Deng, Hongmei; Song, Liping; Cao, Weiguo; Journal of Fluorine Chemistry; vol. 220; (2019); p. 54 – 60;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 552330-86-6,Some common heterocyclic compound, 552330-86-6, name is 5-Bromoisoindolin-1-one, molecular formula is C8H6BrNO, 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.

Intermediate No.175-Bromo-2-(2,2,2-trifluoroethvn-2,3-dihvdro-lH-isoindol-l-one5-Bromo-2,3-dihydro-lH-isoindol-l-one (100 mg, 0.47 mmol) was dissolved inDMF (4.7 mL) and stirred at 0 C. NaH (38 mg, 0.94 mmol, 60% dispersion in oil) was carefully added in two portions, and the resulting mixture was allowed to stir at 0 C for 15 minutes before 2,2,2-trifluoroethyl trifluoromethanesulfonate (110 mg, 0.47 mmol) was added. The mixture was allowed to stir at 0 C 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 MPLC on silica gel (using a gradient elution of 0-20% EtOAc/hexanes). Desired fractions were identified, combined, and concentrated in vacuo to afford the title compound. LRMS (ESI) calc’d for C10H7BrF3NO [M+H]+: 294, Found: 294.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromoisoindolin-1-one, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BRUBAKER, Jason; DINSMORE, Christopher J.; HOFFMAN, Dawn Marie; JUNG, Joon; LIU, Duan; PETERSON, Scott; SIU, Tony; TORRES, Luis E.; ZHANG, Hongjun; WEI, Zhongyong; SHI, Feng; WO2013/40863; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 20870-78-4, These common heterocyclic compound, 20870-78-4, name is 5-Bromoindolin-2-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.

To a solution of commercial available 5-bromoindoline-2-one 2b (425 mg, 2 mmol) and pyrrole 3 (636 mg, 2.4 mmol) in ethanol (4.0 mL) six drops of piperidine were added and the mixture was heated for six hours under reflux. After cooling on ice the precipitate was filtered off, washed with ethanol and dried under vacuum to give 5 (886 mg) as an orange solid in 96% yield, mp: 245-247C, HNMR (d, ppm, DMSO-d): 0.97 (t, 6H, N(CH2CH3)2); 2.43 (s, 3H, CH3); 2.44 (s, 3H, CH3); 2.50 (m, 6H, 3xCH2); 3.29 (m, 2H, NH-CH2); 6.82 (d, 1H, 7-H); 7.25 (d, 1H, 6-H); 7.42 (s, 1H, 4-H); 7.77 (s, 1H, NH-CH2); 8.10 (s, 1H, Hvinyl); 10.99 (s, 1H, NHindole); 13.62 (s, 1H, NHpyrrole); ESI-MS (ES+): m/z=461 (M+H)+

Statistics shows that 5-Bromoindolin-2-one is playing an increasingly important role. we look forward to future research findings about 20870-78-4.

Reference:
Article; Kuchar, Manuela; Oliveira, Maria Cristina; Gano, Lurdes; Santos, Isabel; Kniess, Torsten; Bioorganic and Medicinal Chemistry Letters; vol. 22; 8; (2012); p. 2850 – 2855;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 19155-24-9, name is 3,3-Dimethylindolin-2-one, molecular formula is C10H11NO, 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. Recommanded Product: 19155-24-9

Step 4:3,3-dimethyl-2,3-dihydro-1H-indoleUnder a nitrogen atmosphere a solution of 6.20 mL (6.20 mmol) of a 1M solution lithium aluminium hydride in THF and 10 mL THF was slowly added dropwise to 1.00 g (6.20 mmol) 3,3-dimethyl-1,3-dihydro-indol-2-one in 50 mL THF.Then the reaction mixture was heated to 60¡ã C. for 1 h.After cooling to 0¡ã C., 3 mL ice water were slowly added dropwise.20 g sodium sulphate were added and the mixture was suction filtered.The solution was evaporated down i. vac.Yield: 0.80 g (88percent of theory)ESI-MS: m/z=148 (M+H)+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 19155-24-9, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/195954; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

24566-79-8, name is N-(6-Bromohexyl)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. Formula: C14H16BrNO2

General procedure: To a mixture of the corresponding R1R2NH (3.0 mmol), anhydrous K2CO3 (449 mg, 3.25 mmol) and KI (20.75 mg, 0.125 mmol) in CH3CN (12 ml) were added the appropriate intermediates 6-9 (2.5mmol). The reaction mixture was warmed to 60-65 C and stirred for 6-8 h under an argon atmosphere. After complete reaction, the solvent was evaporated under reduced pressure. Then water (25 mL) was added to the residue and the mixture was extracted with dichloromethane (25 mL¡Á3). The combined organic phases were washed with saturated aqueous sodium chloride (30 mL), dried over sodium sulfate, and filtered. The solvent was evaporated to dryness under reduced pressure. The residue was purified on a silica gel chromatography using mixtures of petroleum ether/EtOAc as eluent, obtaining the corresponding intermediates 10-13a-d.

The synthetic route of 24566-79-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Li, Yuxing; Qiang, Xiaoming; Li, Yan; Yang, Xia; Luo, Li; Xiao, Ganyuan; Cao, Zhongcheng; Tan, Zhenghuai; Deng, Yong; Bioorganic and Medicinal Chemistry Letters; vol. 26; 8; (2016); p. 2035 – 2039;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 552330-86-6,Some common heterocyclic compound, 552330-86-6, name is 5-Bromoisoindolin-1-one, molecular formula is C8H6BrNO, 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 0¡ãC. NaH (415 mg, 10.4 mmol) was added and the mixture stirred under N2 at 0¡ãC 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 (10percent acetone/CH2C12 as eluant). The title compound was isolated as a very pale yellow crystalline solid (1.64 g, 80percent). ? 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.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromoisoindolin-1-one, its application will become more common.

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