Author: tianli

70478-63-6, The chemical industry reduces the impact on the environment during synthesis 70478-63-6, name is 4-Bromoisoindoline-1,3-dione, I believe this compound will play a more active role in future production and life.

A mixture of 3-bromophthalimide (10.0 g, 44.2 mmol), potassium carbonate (12.2 g, 88.5 mmol) and potassium iodide (50 mg, 0.30 mmol) are stirred in 80 mL DMF for 15 min. The reaction mixture is cooled to 0 0C, methyl iodide (3.04 mL, 48.7 mmol) is added and the reaction mixture is stirred overnight at RT. The reaction mixture is filtered, the solids are washed with DMF and the filtrate is poured in water. The mixture is extracted with ethyl acetate and the combined organic phases are washed several times with water, dried over MgSO4 and concentrated in vacuo. Yield: 7.10 g.

The chemical industry reduces the impact on the environment during synthesis 4-Bromoisoindoline-1,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WO2009/112565; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

446292-08-6, name is (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione, 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. 446292-08-6

2 – ({(5S) -2-oxo-3- [4- (3-oxo-4-morpholinyl) phenyl] -1,3-oxazolidin-5- yl} methyl) -1,3 (2H) -dione (Formula 5) Were suspended in 150 ml of ethanol at 22 C ,16.2 g of a methylamine solution (concentration in water of 40%) was added.The reaction mixture is then heated to 60-63 C,The resulting solution was stirred at this temperature for 2 hours.55 C to 60 C After cooling,A total of 33.5 g of a hydrochloric acid solution (20% in water concentration) was added until the pH reached 2.7.After confirming that the crystallization of the product has commenced, After cooling,The precipitated reaction product was filtered under suction, washed with methanol and then dried to give 12.5 g of the desired product. (Yield: 80.5%)

Statistics shows that 446292-08-6 is playing an increasingly important role. we look forward to future research findings about (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione.

Reference:
Patent; IL DONG PHARMACEUTICAL CO., LTD.; LEE, Ki Yong; KWON, Jae Wook; SEO, Myeong Won; KANG, Jae Hoon; (15 pag.)KR2017/98031; (2017); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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: Isatins I (3.0 mmol) was dissolved in anhydrous DMF (15 mL), and the resultant solution was cooled to 0 ¡ãC (ice bath), whereupon sodium hydride (60percent 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 ¡ãC 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 (90percent-100percent yield).

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; 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

Adding some certain compound to certain chemical reactions, such as: 32692-19-6, name is 5-Nitroindoline, 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 32692-19-6. 32692-19-6

General procedure: We described the synthesis of the compound 1 (Table 2) to illustrate the general procedure for TFA accelerated Petasis three-component reaction. The descriptions of the preparations of all reported compounds are in the Supporting information section. To a magnetically stirred mixture of 5-nitroindoline (0.164 g, 1.0 mmol), 4-tolyboronic acid (0.135 g, 1.0 mmol), and glyoxylic acid monohydrate (0.092 g, 1.0 mmol) in CH2Cl2 (5 ml) was added TFA (20 mul). The mixture was stirred at room temperature for 4 h. After the completion of the reaction (TLC monitoring), half of the solvent was evaporated by means of a rotovap. The resulting solid was filtered through a sintered glass funnel. The collected solid was thoroughly washed with petroleum ether and a small amount of ice water (5 ml), and then dried in vacuo at room temperature for 24 h to afford 0.26 g (83.3 %) of 2-(5-nitroindolin-1-yl)-2-(p-tolyl) acetic acid as a light yellow solid.

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 5-Nitroindoline.

Reference:
Article; Zhang, Jing; Yun, Fan; Xie, Rui; Cheng, Chunhui; Chen, Guangyao; Li, Jingxuan; Tang, Pingwah; Yuan, Qipeng; Tetrahedron Letters; vol. 57; 35; (2016); p. 3916 – 3919;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 22120-50-9 as follows. 22120-50-9

A mixture of 2,3-dimethylindoline (0.10 g, 0.679 mmol) and 2-bromoethanaminehydrobromide (0.153 g, 0.747 mmol) was heated at 122 C for 15 h. The mixture was dissolved in 2M HC1 and purified by preparative HPLC to give the title compound (128 mg). LCMS m/z = 191.2[M+H]+.

According to the analysis of related databases, 22120-50-9, the application of this compound in the production field has become more and more popular.

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

5332-26-3, 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. 5332-26-3 name is 2-(Bromomethyl)isoindoline-1,3-dione, 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: The vacuum dried intermediate 3 (0.002 mol) was then reacted with mono- and di-substituted benzoic acids (0.003 mol) separately in presence of anhydrous potassium carbonate (0.003 mol) in DMF (10 mL). The reaction mixture was stirred at room temperature for about 2 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was poured into ice-cold water and allowed stir for 10 min. The solid obtained was filtered and washed successively with distilled water and recrystallized from ethanol to obtain4(a-n).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(Bromomethyl)isoindoline-1,3-dione, and friends who are interested can also refer to it.

Reference:
Article; Kumar, C.S. Chidan; Loh, Wan-Sin; Chandraju, Siddegowda; Win, Yip-Foo; Tan, Weng Kang; Quah, Ching Kheng; Fun, Hoong-Kun; PLoS ONE; vol. 10; 3; (2015);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

6341-92-0, Name is 6-Chloroisatin, 6341-92-0, 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.

General procedure: A mixture of substituted isatin (12.3 mmol), hydrazine hydrate (368 mmol), potassium hydroxide (245 mmol), and ethylene glycol (242 mmol) were heated at 100 C for 1 h. The reaction mixture was cooled on ice bath and acidified using concd HCl (drop wise addition) along with vigorous stirring. The precipitated product was vacuum filtered and washed with hexanes to give substituted indolin-2-ones in 90-95% yield.

Statistics shows that 6-Chloroisatin is playing an increasingly important role. we look forward to future research findings about 6341-92-0.

Reference:
Article; Jha, Mukund; Chou, Ting-Yi; Blunt, Brian; Tetrahedron; vol. 67; 5; (2011); p. 982 – 989;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

20780-72-7, Name is 4-Bromoisatin, 20780-72-7, 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.

General procedure: A solution of 2-nitrobenzamides 1 or bis(2-nitrobenzamides) 4 (1 mmol), isatins 2 or acenaphthylene-1,2-diones 6 (1 mmol), and SnCl2*2H2O (4 mmol) in EtOH (5 mL) was stirred at reflux for 3-5 h. After this period, the TLC analysis of the mixture showed the reaction to be completed. The mixture was quenched with 3percent HCl (10 mL) and filtered to yield a crude product, which was purified by recrystallization from 95percent ethanol and DMF.

Statistics shows that 4-Bromoisatin is playing an increasingly important role. we look forward to future research findings about 20780-72-7.

Reference:
Article; Hu, Yu; Wang, Man-Man; Chen, Hui; Shi, Da-Qing; Tetrahedron; vol. 67; 48; (2011); p. 9342 – 9346;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

897957-06-1, name is 6-Bromo-1-methylindolin-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. 897957-06-1

To I-3.2 (91 mg, 0.40 mmol) in anhydrous dioxane (8 mL) is added R5 (155 mg, 0.61 mmol) and potassium acetate (120 mg, 1.22 mmol). The mixture is purged with Argon, [1,1?-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (PdCl2(dppf)) (33 mg, 0.040 mmol) added and heated to 80 C. for 1.5 h. The reaction mixture is diluted with EA and water, the organic layer washed with brine, dried and concentrated. The residue is purified via column chromatography (cyclohexane/EA=1:1). Yield 100%. m/z 274 [M+H]+, rt 0.71 min, LC-MS Method b.

Statistics shows that 897957-06-1 is playing an increasingly important role. we look forward to future research findings about 6-Bromo-1-methylindolin-2-one.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GRUNDL, Marc; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; RIETHER, Doris; WIENEN, Wolfgang; US2013/172327; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 446292-08-6 name is (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione, 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. 446292-08-6

The above 17.00g white solid, 12.53g methylamine aqueous solution and 360ml methanol were heated to reflux, reacted for 2h at reflux, cooled to 15 C, adjusted to pH 1-2 with concentrated sulfuric acid, and filtered to obtain 11.24g of white solid Yield: 85.0%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione, and friends who are interested can also refer to it.

Reference:
Patent; Hunan Jiu Dian Pharmaceutical Co., Ltd.; Guo Zhe; Lu Guoyan; Tan Wen; Xiao Wending; (13 pag.)CN110818700; (2020); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem