Indolines-derivatives

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

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

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

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

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. 25369-33-9, name is 7-Chloroindolin-2-one, A new synthetic method of this compound is introduced below., name: 7-Chloroindolin-2-one

To a coo?ed (0 C) soution of 7-choroindohn-2-one (1 g, 6.0 mmo) in TFA (11 mL) was added Nbromosuccinimide (1 g, 6.0 mmo) portion wise and stirred the mixture at same temperature for 6 h. Concentrated TFA in vacuo with DCM (25 mL) and then with EtOAc. The crude product was triturated with ethano to provide the tiDe compound as a white soid (861 mg, 58% yie?d). MS (ES):mass cacd, for C6H5BrCNO, 244.9; m/z found, 246.0 [M+H]. 1H NMR (500 MHz, DMSO d6) oe 10.92 (5, 1 H), 7.52 7.48 (m, I H), 7.38 (d, J = 1.2 Hz, I H), 3.62 (s, 2H).

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; JANSSEN PHARMACEUTICA NV; AMERIKS, Michael K.; RAVULA, Suchitra; SAVALL, Bradley M.; SWANSON, Devin M.; ZIFF, Jeannie M.; SHIREMAN, Brock T.; (167 pag.)WO2016/176463; (2016); 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. Safety of 5-Bromo-1-methylindoline-2,3-dione

General procedure: A mixture of an N-substituted isatin (1.0 mmol), benzoyl cyanid (0.145 g, 1.1 mmol), and MS 4A (200 mg) in dry acetonitrile (2 mL) was stirred at room temperature for the indicated time (Table 2). The progress of the reaction was monitored by TLC. After completion of the reaction, the MS 4A was recovered by simple filtration, thoroughly washed with dry acetonitrile. Then the filtrate was evaporated to dryness in a rotary evaporator under reduced pressure and the residue was crystallized from a mixture of CH2Cl2 and petroleum ether, which yielded the pure products.

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

Reference:
Article; Esmaeili, Abbas Ali; Ghalandarabad, Saeid Amini; Zangouei, Mahdieh; Tetrahedron Letters; vol. 53; 42; (2012); p. 5605 – 5607;,
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. 2436-29-5, name is 3-(1,3-Dioxoisoindolin-2-yl)propanal, A new synthetic method of this compound is introduced below., HPLC of Formula: C11H9NO3

General procedure: Neat TiCl4 (120 muL, 1.1 mmol) was added dropwise to a solution of the corresponding alpha-silyloxy methyl ketone (1.0 mmol) in CH2Cl2 (5.0 mL) at -94 C, and the mixture was stirred for 5 min. Then, anhydrous i-Pr2NEt (190 muL, 1.1 mmol) was added dropwise and the resulting dark red solution was stirred for 30 min at -94 C. After dropwise addition of the freshly distilled aldehyde (1.5 mmol), stirring was continued for 30 min at -78 C. The reaction was quenched by the addition of saturated NH4Cl (5 mL) and vigorously stirred at room temperature for 10 min. Then it was diluted with Et2O (50 mL), and washed with H2O (50 mL), saturated NaHCO3 (50 mL) and brine (50 mL). The combined organic extracts were dried (MgSO4) and concentrated. The resulting crude was analysed by 1H NMR and purified by column chromatography.

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:
Article; Lorente, Adriana; Pellicena, Miquel; Romea, Pedro; Urpi, Felix; Tetrahedron; vol. 71; 7; (2015); p. 1023 – 1035;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 201940-08-1,Some common heterocyclic compound, 201940-08-1, name is tert-Butyl 5-bromoisoindoline-2-carboxylate, molecular formula is C13H16BrNO2, 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.

A mixture of 5-bromo-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester (200 mg, 0.67 mmol), Pd (OAc) 2 (30 mg, 0.2 equiv), DPPP (55 mg, 0.2 equiv), TEA (0.93 mL, 10 equiv) and MeOH : DMSO (1: 1,4 mL) was stirred for 16 h under CO (balloon) at 80 C. LC-MS and TLC (20% EtOAc-Hexane) showed completion of the reaction. The Reaction mixture was concentrated to remove MeOH and diluted with EtOAc (10 mL), and washed with water (2 x 25 mL). The organic layer was dried (Na2S04), concentrated and purified by silica gel column chromatography (eluent = 20% EtOAc-Hexane), giving pure 1, 3-dihydro-isoindole-2,5- dicarboxylic acid 2-tert-butyl ester 5-methyl ester (150 mg, 81 %). MS (APCI+) : m/z 178.1 (MH+-Boc).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl 5-bromoisoindoline-2-carboxylate, its application will become more common.

Reference:
Patent; INTERMUNE, INC.; ARRAY BIOPHARMA INC.; WO2005/37214; (2005); A2;,
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. HPLC of Formula: C13H14BrNO2

General procedure: To a stirred solution of 2-5 (5 mmol) in THF (60 mL) was added potassium thioacetate (15 mmol), and the mixture was refluxed for 3-4 h. And the solvent was evaporated to dryness in vacuo, and then added water (30 mL), and the organic materials were extracted with EtOAc (3×30 mL). The combined extracts were washed with water and brine, dried over anhydrous MgSO4, and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (EtOAc:petroleum ether=1:8) to give compounds 6-9 as white powder.

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

Reference:
Article; Hu, Kun; Qi, Yan-Jie; Zhao, Juan; Jiang, He-Fei; Chen, Xin; Ren, Jie; European Journal of Medicinal Chemistry; vol. 64; (2013); p. 529 – 539;,
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. 2058-74-4, name is 1-Methylisatin, This compound has unique chemical properties. The synthetic route is as follows., name: 1-Methylisatin

A solution of N-methylisatin (322 mg, 2.0 mmol), indole (258 mg, 2.2 mmol), and K2CO3 (138 mg, 1.0 mmol) in aqueous DMF (H2O/DMF, 2:1, 5.0 mL) was heated to 50 oC for 3 h. After aqueous extractive workup and column chromatographic purification process (n-hexane/EtOAc, 1:1), 3-hydroxy-3-(1H-indol-3-yl)-1-methylindolin-2-one (1m) was obtained as a white solid, 340 mg (61%).1 To a stirred solution of 1m (278 mg, 1.0 mmol) in DMF (3.0 mL) was added t-BuOK (125 mg, 1.1 mmol) and iodomethane (158 mg, 1.1 mmol) successively at 0 oC. The reaction mixture was stirred at room temperature for 2 h. After aqueous extractive workup and column chromatographic purification process (n-hexane/EtOAc, 3:1), compound 1a was obtained as a white solid, 185 mg (63%).

According to the analysis of related databases, 2058-74-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Seo, Da Young; Roh, Hwa Jung; Jo, Hwi Yul; Cho, Sung; Kim, Jae Nyoung; Tetrahedron Letters; vol. 59; 11; (2018); p. 1005 – 1009;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem