Category: indolines-derivatives

Adding a certain compound to certain chemical reactions, such as: 496-12-8, name is Isoindoline, 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 496-12-8, category: indolines-derivatives

To a stirred mixture of 17(4 g, 9.68 mmol) in anhydrousdichloromethane (50 mL) was added DIPEA (8.45mL, 48.4 mmol), HOBt (2.96g,19.36mmol),followed by EDCI·HCl (3.71g, 19.36 mmol) and isoindoline(2.197ml, 19.36 mmol). After the addition, the mixture was stirred at roomtemperature overnight. The mixture was diluted with dichloromethane (100 mL),washed with 2N HCl,sat. NaHCO3,H2O,brine and dried over anhydrous Na2SO4. Thesolvent were then concentrated in vacuo .The residue was recrystallized from a 20%DCM in Petroleum ether to afford the product (2,4-bis(benzyloxy)-5-bromophenyl)(isoindolin-2-yl)methanone18 asa white solid (3.5g, 70%),which was used in the next step without furtherpurification.1HNMR (400 MHz, Chloroform-d) delta 7.52 (s, 1H), 7.45-7.26 (m, 12H), 7.25-7.23(m, 1H), 7.12 (d, J = 7.2 Hz, 1H), 6.57 (s, 1H), 5.11 (s, 2H), 5.05 (s,2H), 4.96 (s, 2H), 4.62 (s, 2H).MS(ESI) : m/z 514 (M+H)+.Retention timeof 4.53 min, >99% pure.

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

Reference:
Article; Ren, Jing; Li, Jian; Wang, Yueqin; Chen, Wuyan; Shen, Aijun; Liu, Hongchun; Chen, Danqi; Cao, Danyan; Li, Yanlian; Zhang, Naixia; Xu, Yechun; Geng, Meiyu; He, Jianhua; Xiong, Bing; Shen, Jingkang; Bioorganic and Medicinal Chemistry Letters; vol. 24; 11; (2014); p. 2525 – 2529;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6941-75-9, name is 5-Bromoisoindoline-1,3-dione, 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 6941-75-9, COA of Formula: C8H4BrNO2

In a stirred three-necked reaction flask, 100 g of 4-bromophthalimide, 62 g of phenol, 92 g of potassium carbonate, 6.5 g of cuprous bromide, 7 g of N, N-dimethylglycine, 200 mL of 1,4 – dioxane, in the N2 protection, the system temperature to 85 C reaction, 24 hours after the complete reaction of the raw materials, vacuum distillation of dioxane; by adding 300mL of methylene chloride dissolved products After filtration, the filtrate was evaporated to dryness, and 100 mL of methanol was added. The temperature was raised to 40 C for 1 hour. The temperature of the system was reduced to -5 to 0 C, After stirring for 5 hours, the mixture was filtered and dried to obtain 85 g of a white crystalline solid, Yield 80% HPLC purity 98%

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromoisoindoline-1,3-dione, and friends who are interested can also refer to it.

Reference:
Patent; Lianhua Technology Co., Ltd.; Zou Benli; Xie Siwei; Yuan Li; Cui Yan; (22 pag.)CN107188875; (2017); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 675109-45-2, A common heterocyclic compound, 675109-45-2, name is 6-Amino-2,3-dihydro-1H-isoindol-1-one, molecular formula is C8H8N2O, 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 Intermediate 6 (0.1 g, 0.675 mmol) and 4-fluoro-3- methoxyphenylboronic acid (0.115 g, 0.675 mmol) in acetonitrile (1.8 mL) and DMF (0.50 mL) was added 2-oxoacetic acid (0.062 g, 0.675 mmol). The reaction was mixture was sonicated for 5 minutes and heated to 90 0C for 20 min on a biotage microwave. The solvent was concentrated and the crude product was dissolved in a small amount of chloroform and charged to a 40 g silica gel cartridge which was eluted with a 40 min gradient time from 0-20% methanol / dichloromethane. The product peak was isolated and dried to give 24A (0.086 g, 39%) brown solid product. 1H NMR (400 MHz, methanol-d4) delta ppm 3.82 – 3.88 (m, 3 H) 4.25 – 4.31 (m, 2 H) 5.10 (s, 1 H) 6.88 – 7.01 (m, 2 H) 7.02 – 7.13 (m, 2 H) 7.23 – 7.32 (m, 2 H); MS (ESI)(m/z) 331.3 [M+H]+ .

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; BRISTOL-MYERS SQUIBB COMPANY; WO2008/79759; (2008); 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. 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., category: indolines-derivatives

In a pear-shaped flask, compound 1 (see Fig. S5b) was synthesised by reacting sodium (0.3615 g, 15.7 mmol) and mercury (2.1 mL, 13.4 mmol) under an argon atmosphere. A violent formation of the amalgam resulted and this was allowed to cool down before dry and degassed THF was added. Cyclopentadienyliron dicarbonyl dimer (1.009 g, 2.85 mmol) was added and the reaction mixture was stirred at room temperature for two hours. The yellowish brown metallate was transferred into a RBF (kept at -78 C) by means of a canula. The reaction mixture was transferred into a flask already containing bromomethylphthalimide (0.953 g, 3.97 mmol) dissolved in approximately 15 mL of dry and degassed THF. The reaction mixture was allowed to stir at -78 C for two hours before being allowed to stir at room temperature for a further three hours. After removal of solvent under reduced pressure the residue was chromatographed on silica using DCM as eluent. The yellow band, which eluted out second, was collected and concentrated. The final product was obtained as a yellow powder. Yield: (1.074 g, 80%): m.p. 181 C, 1H-NMR (400 MHz, CDCl3, ppm) deltaH = 4.05 (2H,s, Fe-CH2), 4.91 (5H, s, C5H5), 7.70 (4H, m, C6H4). 13C-NMR (100 MHz, CDCl3, ppm) deltaC =11.14 (Fe-CH2), 85.36 (Cp moiety), 122.5 (2C, Ar-CH), 132.8 (2C, Ar-C), 133.4 (2C, Ar-CH), 168.7 (NCO), 215.5 (terminal CO). IR (ATR, cm-1): 1997 (terminal CO), 1951 (terminal CO),1751, 1701. CHN analysis for C16H11FeNO4 Calculated: C; 57.01, H; 3.29, N; 4.15. Found: C;57.16, H; 3.34, N; 4.18.

The synthetic route of 5332-26-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nyamori, Vincent O.; Bala, Muhammad D.; Mkhize, Dennis S.; Journal of Organometallic Chemistry; vol. 780; (2015); p. 13 – 19;,
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 5332-26-3 as follows. Product Details of 5332-26-3

2-Ethylacrylic acid (250 mg, 2.5 mmol) was dissolved in anhydrous dimethylformamide (8.0 mL), to the solution were added N-bromomethylphthalimide (660.0 mg, 2.8 mmol) and potassium fluoride (291.0 mg, 5.0 mmol), and the mixture was stirred for 12 hr at 80 C. under nitrogen atmosphere. The reaction mixture was concentrated in vacuo, and the obtained residue was extracted with dichloromethane after the addition of water (80 mL). The organic layer was dried over magnesium sulfate and concentrated in vacuo, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to obtain the objective substance (463.1 mg, 72%). 1H-NMR (CDCl3) delta: 7.94 (dd, J=5.4, 3.2 Hz, 2H), 7.79 (dd, J=2.8, 1.4 Hz, 2H), 6.16 (d, J=1.0 Hz, 1H), 5.80 (s, 2H), 5.57 (d, J=1.5 Hz, 1H), 2.35-2.25 (m, 2H), 1.06 (t, J=7.4 Hz, 3H).

According to the analysis of related databases, 5332-26-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TEIJIN PHARMA LIMITED; US2005/182032; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

39603-24-2, name is 5,7-Dimethylindoline-2,3-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. Application In Synthesis of 5,7-Dimethylindoline-2,3-dione

General procedure: A mixture of aromatic diamine derivatives (2 mmol) and a 1,2-dicarbonyl compound (2 mmol) in ionic liquid (2 mL) was stirred atroom temperature for the appropriate time. The progress of the reaction was monitored by TLC (n-Hexane: EtOAc, 7:3), after completion of the reaction, the reaction mixture was diluted with water and extracted using diethyl ether (30 ml). The combined organic layer was dried over anhydrous sodium sulphate and evaporated under reduced pressure to afford the corresponding product. The residual ionic liquid was dried under vacuum and reused. The same procedure was repeated for the reaction of aromatic anilines with isatin and acenaphthoquinone and phenaacylbromide. All the products obtained were characetrised by IR,1HNMR, 13CNMR and Mass studies.

The synthetic route of 39603-24-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bhargava, Sangeeta; Soni; Rathore, Deepti; Journal of Molecular Structure; vol. 1198; (2019);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 923590-95-8,Some common heterocyclic compound, 923590-95-8, name is 4-Bromoisoindoline hydrochloride, molecular formula is C8H9BrClN, 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.

4-Bromoisoindoline hydrochloride (3.0 g, 13 mmol, 1 eq) was suspended in dry DCM (50 ml), and then TEA (5.4 ml, 39 mmol, 3 eq) was added. Reaction mixture was cooled to 0C in an ice-bath, and then benzyl chloroformate (2.7 ml, 19 mmol, 1 .5 eq) dissolved in 10 ml DCM was added dropwise. Reaction was carried out under inert gas (nitrogen) atmosphere while stirring at room temperature for 3h. Reaction mixture was extracted thrice with saturated NaHCC solution, then once with water and with saturated NaCl solution. Organic phase was dried over anhydrous Na2S04, and then concentrated under reduced pressure to obtain white solid which was dried under vacuum. (0165) White solid, yield: 90% (3.8 g), Ci6Hi4BrN02, MW 332.19, monoisotopic mass 331 .02, [M+H]+ 332.2, UPLC Rt = 8.12. 1H NMR (300 MHz, CDCU) d (ppm) 4.73 (dd, J= 1 1 .6, 1 .4 Hz, 2H), 4.79-4.89 (m, 2H), 5.22 (d, J = 2.2 Hz, 2H), 7.09-7.50 (m, 7H).

The synthetic route of 923590-95-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CELON PHARMA S.A.; UNIWERSYTET JAGIELLONSKI; INSTYTUT FARMAKOLOGII POLSKIEJ AKADEMII NAUK; KAMINSKI, Krzysztof; GRYCHOWSKA, Katarzyna; CANALE, Vittorio; BOJARSKI, Andrzej J.; SATALA, Grzegorz; LENDA, Tomasz; POPIK, Piotr; MATLOKA, Mikolaj; DUBIEL, Krzysztof; MOSZCZYNSKI-PETKOWSKI, Rafal; PIECZYKOLAN, Jerzy; WIECZOREK, Maciej; ZAJDEL, Pawel; (69 pag.)WO2019/97282; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 14192-26-8, 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. 14192-26-8, name is Methyl 2-oxoindoline-6-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of methyl 2-oxoindoline-6-carboxylate (4.08 g) and Mel (6.12 g) in DMF (61 ml) was added at 22 C NaH (1.71 g) over a period of 1.5 h and stirring was continued for 4 h. The mixture was partitioned between aqueous hydrochloric acid (1 M) and EtOAc, the organic layer was dried, evaporated and the residue purified by flash chromatography (silica gel, gradient, 0% to 100% EtOAc in n-heptane) to give the title compound (0.64 g, 13%) as a brown solid. MS (ESI, m/z): 234.5 [(M+H)+]. The second fraction contained 3,3-dimethyl-2-oxo-2,3-dihydro-lH- indole-6-carboxylic acid methyl ester (3.82 g, 82%) as brown solid. MS (ESI, m/z): 220.5 [(M+H)+].

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

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HILPERT, Hans; KOLCZEWSKI, Sabine; LIMBERG, Anja; STOLL, Theodor; WO2015/177110; (2015); 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. 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. name: 5-Bromo-1-methylindoline-2,3-dione

General procedure: To a boiling slurry of 1 mmol of imidazothiazolotriazine hydrobromide 1a and 1b and 1 mmol of an appropriate isatin 2 in 15 mL of methanol, 0.108 mL of 40% water solution of KOH was added. The reaction mixture was stirred for 2 h. The precipitate separated on cooling the reaction mixture was filtered off, if necessary recrystallized from methanol, and dried.

The synthetic route of 2058-72-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Izmest?ev; Gazieva; Kulikov; Anikina; Kolotyrkina; Kravchenko; Russian Journal of Organic Chemistry; vol. 53; 5; (2017); p. 753 – 763; Zh. Org. Khim.; vol. 53; 5; (2017); p. 741 – 750,10;,
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. 193354-13-1, name is 5-Iodoindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., Safety of 5-Iodoindolin-2-one

5-Methoxycarbonyl-2-oxindole 5-Iodo-2-oxindole (17 g) was refluxed with 2 g of palladium diacetate, 18.2 g of triethylamine, 150 ML of methanol, 15 ML of dimethylsulfoxide and 2.6 g of DPPP in an atmosphere saturated with carbon monoxide.. After 24 hours, the reaction was filtered to remove the catalyst and the filtrate concentrated.. The concentrate was chromatographed on silica gel (30% ethyl acetate in hexane).. The fractions containing product were concentrated and allowed to stand.. The precipitated product was collected by vacuum filtration to give 0.8 g (7%) of the title compound as an off-white solid.

According to the analysis of related databases, 193354-13-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sugen, Inc.; US6350754; (2002); B2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem