Category: 496-12-8

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: 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, Application In Synthesis of Isoindoline

Example 94 N-[5-(1,3-dihydro-isoindol-2-yl-carbonyl)-1-methyl-pyrrol-3-yl]-4′-trifluoromethyl-biphenyl-2-carboxylic acid amide Prepared analogously to Example 1d from 4-(4′-trifluoromethyl-biphenyl-2-carbonylamino)-1-methyl-pyrrole-2-carboxylic acid, 2,3-dihydro-1H-isoindole, TBTU and N-ethyldiisopropylamine in dimethylformamide. Yield: 79% of theory Rf value: 0.64 (silica gel; dichloromethane/ethanol=9:1)

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, Isoindoline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Boehringer Ingelheim Pharma KG; US2003/162788; (2003); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 496-12-8, These common heterocyclic compound, 496-12-8, name is Isoindoline, 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.

In a 1L round bottom flask were mixed bis(2,5-dioxopyrrolidin-1-yl) carbonate (11.08 g, 43.2 mmol), tert-butyl 4-(4-aminophenyl)piperidine-1-carboxylate (9.96 g, 36.0 mmol), and anhydrous pyridine (2.91 ml, 36.0 mmol) in anhydrous acetonitrile (181 ml). The mixture was stirred overnight at room temperature when DIEA (12.59 ml, 72.1 mmol) was added to the reaction followed by dropwise addition of isoindoline (4.29 g, 36.0 mmol) in anhydrous acetonitrile (20 ml) and anhydrous DMF (10 ml). The solution darkened and then became a suspension after 1-2 h; this mixture was stirred overnight when it was quenched with 300 ml water, stirred vigorously for 1 h and filtered with water washes to give after drying 13.92 g of product as a brown solid.

Statistics shows that Isoindoline is playing an increasingly important role. we look forward to future research findings about 496-12-8.

Reference:
Article; Curtin, Michael L.; Heyman, H. Robin; Clark, Richard F.; Sorensen, Bryan K.; Doherty, George A.; Hansen, T. Matthew; Frey, Robin R.; Sarris, Kathy A.; Aguirre, Ana L.; Shrestha, Anurupa; Tu, Noah; Woller, Kevin; Pliushchev, Marina A.; Sweis, Ramzi F.; Cheng, Min; Wilsbacher, Julie L.; Kovar, Peter J.; Guo, Jun; Cheng, Dong; Longenecker, Kenton L.; Raich, Diana; Korepanova, Alla V.; Soni, Nirupama B.; Algire, Mikkel A.; Richardson, Paul L.; Marin, Violeta L.; Badagnani, Ilaria; Vasudevan, Anil; Buchanan, F. Greg; Maag, David; Chiang, Gary G.; Tse, Chris; Michaelides, Michael R.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 15; (2017); p. 3317 – 3325;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 496-12-8,Some common heterocyclic compound, 496-12-8, name is Isoindoline, molecular formula is C8H9N, 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.

(5-bromo-2,4-dihydroxyphenyl)(isoindolin-2-yl)methanone, 7 (PA1): In a 50 mL, three-necked, round-bottomed flask, 5-bromo-2,4-dihydroxybenzoic acid (1.42 g, 5.65 mmol, 1.13 equivalent), l-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC, 1.02 g, 5.25 mmol, 1.05 equivalent) and 1-Hydroxybenzotriazole (HOBT, 776 mg, 5.75 mmol, 1.15 equivalent) were dissolved in dimethylformamide (10 mL) at room temperature. The mixture was stirred at the same temperature for 30 min before isoindoline (596 mg, 5 mmol, 1 equivalent) was added. After 18 h, the reaction mixture was diluted with ethyl acetate (50 mL) and washed sequentially with IN HC1 aqueous solution, saturated aqueous aHC03, and brine. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel; ethyl acetate: hexanes 1 :20 to 1 : 1) to yield PAl (1.17 g, 70% yield). XH NMR (500 MHz, DMSO-d6) delta 10.50 (s, 1H), 10.34 (s, 1H), 7.38-7.36 (m, 2H), 7.34 (s, 1H), 7.29-7.27 (m, 2H), 6.59 (s, 1H), 4.77 (s, 2H), 4.70 (s, 2H); 13C NMR (125 MHz, DMSO-d6) delta 166.6, 155.8, 154.7, 136.9, 131.7, 127.4, 122.9, 117.2, 103.7, 98.6, 52.7 (Rotamers were observed). LRMS (ESI) calculated for [M+H]+ 334.0, found 333.9.

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

Reference:
Patent; THE BOARD OF REGENTS OF THE UNIVERSITY OF TEXAS SYSTEM; CHUANG, David, T.; TSO, Shih-Chia; QI, Xiangbing; GUI, Wen-Jun; WU, Cheng-Yang; CHUANG, Jacinta, L.; TAMBAR, Uttam, K.; WYNN, R., Max; WO2015/89360; (2015); A1;,
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, Recommanded Product: 496-12-8

General procedure: A literature procedure1 was modified by replacing triethylamine with N,N-diisopropylethylamine. To a stirred mixture of tetrahydroisoindoline (0.11 mL, 1.0 mmol), N-Boc-(R)-phenylalanine (265 mg, 1.0 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (182 mg, 1.0 mmol) and anhydrous 1-hydroxybenzotriazole (203 mg, 1.5 mmol) in N,N-dimethylformamide (3.0 mL) was added N,N-diisopropylethylamine (1.3 mL, 7.5 mmol). The mixture was stirred at 20 for 16 h. The solvent was evaporated and the residue was dissolved in ethyl acetate (20 mL) and the solution was washed with water (2 x 20 mL). The combined aqueous fractions were re-extracted with ethyl acetate (2 x 20 mL) and all the combined organic layers were washed with saturated aqueous sodium hydrogen carbonate (2 x 20 mL) then with brine (20 mL) filtered and dried (MgSO4). Column chromatography (25:75 ethyl acetate: dichloromethane) of the residue gave 7c (175 mg, 48%) as a cream solid,

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; Chan, A. W. Edith; Greenwood, Simon O. R.; Hansen, D. Flemming; Marson, Charles M.; Bioorganic and medicinal chemistry letters; (2020);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 496-12-8, These common heterocyclic compound, 496-12-8, name is Isoindoline, 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.

3-lodobenzoic acid (248 mg, 1.0 mmol), isoindoline (284 uL, 1.5 mmol), and triethylamine (420 uL, 3.0 mmol) were dissolved in 10 ml. of CH2CI2 and treated with HOBt (203 mg, 1.5 mmol) and EDC (288 mg, 1.5 mmol). The reaction was stirred at room temperature overnight. The reaction mixture was concentrated, diluted with EtOAc, and washed with water, 1N HCI, and brine. The organic layer was dried (MgSO4), filtered, and concentrated. The crude residue was purified by flash chromatography on silica gel (CH2CI2/Et0Ac) to yield 304 mg (87%) of the product as a tan solid. MS (+ESI): m/z 349.9 [M+H]+.

Statistics shows that Isoindoline is playing an increasingly important role. we look forward to future research findings about 496-12-8.

Reference:
Patent; WYETH LLC; LI, David, Zenan; O’NEIL, Steven, Victor; SPRINGER, Dane, Mark; ZEGARELLI, Benjamin, Miller; WO2010/124047; (2010); A1;,
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, Application In Synthesis of Isoindoline

A mixture of 31 -1 (100 mg, 0.306 mmol), isoindoline (47 mg, 0.398 mmol) and HATU (232 mg, 0.611 mmol) in THF (10 mL) was stirred for 10 min at room temperature. DIPEA (99 mg, 0.764 mmol) was added and the reaction mixture was stirred overnight. The volatiles were evaporated and the resulting residue was partitioned between ethyl acetate (10 mL) and water (10 mL). The organic layer was separated and washed with brine (3 X 10 mL), dried over Na2SO4 and concentrated under vacuum. The resulting residue was purified on silica gel column chromatography eluting with dichloromethane/methanol (100: 1) to afford 31 -2 (180 mg, 70%) as a white solid. LRMS: calc 428.2 and found: 429.1 [M+l].General conditions for step 1: amine, BOP, TEA in DMF .

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, Isoindoline, other downstream synthetic routes, hurry up and to see.

Synthetic Route of 496-12-8, The chemical industry reduces the impact on the environment during synthesis 496-12-8, name is Isoindoline, I believe this compound will play a more active role in future production and life.

Step 1: Boc-4-Oxo-proline methyl ester (100 mg, 0.41 mmol) and isoindoline (51 pL, 0.43 mmol) were dissolved in DCE (1 .5 mL) and acetic acid (25 pL, 0.41 mmol) added. After 1 hour, NaBH(OAc)3 (261 mg, 1 .23 mmol) was added and the reaction mixture stirred at room temperature overnight. The reaction mixture was diluted with sat. aq. NaHCO3 and extracted with DCM. The combined organics were passed through a phase separator and the solvent removed to give acrude product which was purified by column chromatography (Biotage, 1 Og SNAP, 0-80% EtOAc/ihexane) to give (25,4R)-4-(1 ,3-dihydro-isoindol-2-yl)-pyrrolidine-1 ,2-dicarboxylic acid 1-tert- butyl ester 2-methyl ester (0.1 3g, 92%) as a brown oil.AnalpH2_MeOH_4MIN: Rt: 1.99 mi mlz 347.3 [M+H]+

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, Isoindoline, other downstream synthetic routes, hurry up and to see.

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. 496-12-8, name is Isoindoline, A new synthetic method of this compound is introduced below., Product Details of 496-12-8

General procedure: Isoindoline (0.5 g, 4.2 mmol, 1.0 equiv) was dissolved in dry pyridine (10 ml). Methane sulfonyl chloride (0.65 g, 5.9 mmol, 1.4 equiv) was added dropwise and the reaction mixture was stirred overnight at rt. Monitoring by HPLC and LCMS indicated that the reaction was completed. The solvent was evaporated under reduced pressure. A solution of HCl 1N (50 mL) and EtOAc (50 mL) were added. The organic layer was separated and the aqueous phase was extracted twice with EtOAc (2×50 mL). The combined organic phase was dried over Na2SO4 and the solvent was evaporated under reduced pressure to yield the pure product: 325 mg, 39 % yield.

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.

Related Products of 496-12-8, A common heterocyclic compound, 496-12-8, name is Isoindoline, molecular formula is C8H9N, 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.

Step two:Add to 50mL DMSO7-(4-Chlorophenyl)-1,8-naphthyridin-2-ylcarbamate (5.0 mmol) and isoporphyrin(5.5mmol),Stir at 80 C overnight.The reaction mixture was quenched with water (200 mL)Combine the organic phase,Wash with saturated sodium chloride solution,Dry over anhydrous sodium sulfate,filter,The residue was purified by silica gel column chromatography (hexane: methanol:Obtain a title in the form of a white solidCompound 1.59g,The yield was 79.6%.

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