Month: March 2021

Reference of 56341-37-8, A common heterocyclic compound, 56341-37-8, name is 6-Chlorooxindole, molecular formula is C8H6ClNO, 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.

General procedure: To the phenstatin-3-aldehyde/isocombretastatin-3-aldehyde(16a-b) (0.303 mmol/0.304 mmol) prepared in the above stepwas added corresponding substituted oxindoles (17a-h)(0.303 mmol) and catalytic amount of piperidine (1.0 ml) in ethanol.Heated the reaction mixture to reflux for 4 h at 85 C. The solidcompounds obtained in the reaction vessel were filtered and washed with ethanol for 4-5 times. After complete air drying thefinal compounds phenstatin/isocombretastatin-oxindole analogs(5a-h and 6a-h) were obtained as pure solids (yield 71-90%).

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; Kumar, G. Bharath; Nayak, V. Lakshma; Sayeed, Ibrahim Bin; Reddy, Vangala Santhosh; Shaik, Anver Basha; Mahesh, Rasala; Baig, Mirza Feroz; Shareef, Mohd Adil; Ravikumar; Kamal, Ahmed; Bioorganic and Medicinal Chemistry; vol. 24; 8; (2016); p. 1729 – 1740;,
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Application of 18711-13-2,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.

General procedure: To a solution of isatin 1 (1 mmol) in toluene (5 mL) was added the solution of trialkyl/aryl Al 2 (2 mmol, 2 M in toluene) dropwise at RT. Then the mixture was heated at 70 C and stirred for additional 3-3.5 h (see Table 2). The reaction was monitored by TLC. After completion of the reaction, toluene was evaporated and extracted with ethyl acetate (3 ¡Á 5 mL). The combined organic layer was washed with brine solution, dried over anhydrous Na2SO4, and concentrated under reduced pressure (rotary evaporator). The crude products were purified by silica gel column chromatography using ethyl acetate/hexanes (4:1-1:1). All compounds were characterized by (MP, NMR, Mass, and IR) spectral data.18

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4,7-Dichloroindoline-2,3-dione, its application will become more common.

Reference:
Article; Kumar, G. Santosh; Ramesh, Palakuri; Kumar, A. Sanjeeva; Swetha; Meshram; Tetrahedron Letters; vol. 54; 37; (2013); p. 5048 – 5051;,
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Indoline | C8H9N – PubChem

Some common heterocyclic compound, 101207-45-8, name is 2-(4-Methylbenzyl)isoindoline-1,3-dione, molecular formula is C16H13NO2, 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. Product Details of 101207-45-8

Add 50 mg of 2- (4-methylbenzyl) -isoindololine-1,3-dione (0.2 mmol), 1.2 mg of potassium hydroxide to a glass test tube with magnetons,Add 2 ml of isopropanol under nitrogen protection,Adding 20 microliters of 0.001M catalyst (S / C = 10,000),Subsequently, the reaction flask was transferred to an autoclave, the reaction kettle was tightened, 3 MPa of hydrogen was charged, and the reaction was carried out at 40 C for 20 hours. After the reaction was completed, the mixture was naturally cooled to room temperature, and the hydrogen gas was carefully released. The celite was filtered, and the organic solvent was removed from the filtrate to obtain 51 mg of a white solid with a yield of 99%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 101207-45-8, its application will become more common.

Reference:
Patent; South University of Science and Technology of China; Ma Baode; Shao Panlin; Wu Chao; Wang Jiang; Zhang Xumu; (12 pag.)CN110734384; (2020); A;,
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Some common heterocyclic compound, 7147-90-2, name is 5-Chloroisoindoline-1,3-dione, molecular formula is C8H4ClNO2, 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 5-Chloroisoindoline-1,3-dione

General procedure: (0.107) Intermediate 4 (0.001 mol) was dissolved in 15 ml of N ‘N-dimethylformamide solution, anhydrous potassium carbonate (0.00 mol) was added, methyl iodide (0.0015 mol) or benzyl chloride (0.0015 mol)The mixture was stirred at room temperature for 5 hours. The filtrate was distilled off and the solvent was distilled off, and the residue was recrystallized from methanol to give the intermediate compound 17. 17a: near white solid, yield 53.1%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7147-90-2, its application will become more common.

Reference:
Patent; Shandong University; Zhao Guisen; Liu Yang; Geng Jingkun; Li Yijing; (15 pag.)CN104447496; (2017); B;,
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Electric Literature of 3676-85-5, These common heterocyclic compound, 3676-85-5, name is 5-Aminoisoindoline-1,3-dione, 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.

A mixture of the appropriate amine (1 mmol) and the appropriate benzyl bromide (1 mmol) inDMF (0.5 M) was stirred at 60 C until completion of the reaction (up to 40 hours). The reactionmixture was quenched with sat. NaHCO3 and extracted with EtOAc. Crude material was purified by automated flash chromatography (EtOAc:hexanes mixture) to give the desired compound in 12-20% yield; ?H NIVIR (400 MHz,DMSO) 10.81 (s, 1H), 7.64 (d, J= 8.5 Hz, 2H), 7.53 (d, J= 8.5 Hz, 1H), 7.12 (s, 1H), 7.02 (d, J= 2.1 Hz, 1H), 6.95 (dd, J= 8.5, 2.1 Hz, 1H), 4.49 (s, 2H). ?3C NIVIR (101 1VIHz, DMSO) 170.03(s), 169.78 (s), 161.37 (d, J= 250.6 Hz), 154.06 (s), 136.95 (s), 136.83 (s), 135.86 (s), 130.28 (s),125.00 (s), 119.02 (s), 117.02 (s), 116.77 (s), 42.79 (s).

Statistics shows that 5-Aminoisoindoline-1,3-dione is playing an increasingly important role. we look forward to future research findings about 3676-85-5.

Reference:
Patent; THE CENTRE FOR DRUG RESEARCH AND DEVELOPMENT; THE UNIVERSITY OF BRITISH COLUMBIA; ROBERGE, Michel; BARADARAN-HERAVI, Alireza; BALGI, Aruna D.; ZIMMERMANN, Carla D.; KRAUSE, Alexandra; PFEIFER, Thomas Arthur; JAQUITH, James Brian; TAN, Jason Samuel; SHIDMOOSSAVEE, Fahimeh S.; ARNS, Stephen Paul; BAUDELET, Davy Jeremy; (354 pag.)WO2017/49409; (2017); A1;,
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Related Products of 110568-64-4, 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. 110568-64-4, name is 6-Nitroisoindolin-1-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 5-nitroisoindolin-l-one (600 mg, 3.37 mmol) in dioxane (30 mL) under a nitrogen atmosphere was added DMAP (616 mg, 5.05 mmol) followed by di-to -butyl dicarbonate (1.16 mL, 5.05 mmol). The resulting reaction mixture was stirred at room temperature overnight, then poured onto water and extracted with EtOAc (3X). The combined organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude residue was purified by chromatography (20% EtOAc in hexanes eluent followed by 20:20:80 DCM: EtOAc: hexane eluent) to provide tot-butyl 5-nitro-l-oxoisoindoline-2-carboxylate (576 mg, 61% yield) as a white solid. NMR (300 MHz, Chloroform-i ) delta 8.43 – 8.35 (m, 2H), 8.10 (d, J = 8.9 Hz, 1H), 4.90 (s, 2H), 1.64 (s, 9H).

The synthetic route of 6-Nitroisoindolin-1-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY OF HAWAII; TURKSON, James; YUE, Peibin; TIUS, Marcus; BROTHERTON-PLEISS, Christine; LOPEZ TAPIA, Francisco, Javier; (420 pag.)WO2018/136935; (2018); A1;,
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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. 24566-79-8, name is N-(6-Bromohexyl)phthalimide, A new synthetic method of this compound is introduced below., Application In Synthesis of N-(6-Bromohexyl)phthalimide

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 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; 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,
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Reference of 5332-26-3,Some common heterocyclic compound, 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, molecular formula is C9H6BrNO2, 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.

Diethyl (aminomethyl)phosphonate was synthesized according to literature procedure (see Kalman et a. Inorg. Chem. 2007, 46, 5260) The compound was isolated as yellow liquid 64% yield (1.082g).?H NMR (300 MHz, CDC13) 4.17-4.08 (m, 4H), 3.01 (d, J 10.3 Hz, 2H), 1.85 (bs, 2H), 1.34 (t, J 7.1 Hz, 6H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(Bromomethyl)isoindoline-1,3-dione, its application will become more common.

Reference:
Patent; THE ROYAL INSTITUTION FOR THE ADVANCEMENT OF LEARNING/MCGILL UNIVERSITY; TSANTRIZOS, Youla S.; POIRIER, Judes; SEBAG, Michael; BERGHUIS, Albert; PARK, Jaeok; WIM DE SCHUTTER, Joris; WO2014/78957; (2014); A1;,
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Synthetic Route of 264916-06-5, 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. 264916-06-5, name is tert-Butyl 5-aminoisoindoline-2-carboxylate belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A solution of 2-Boc-5-aminoisoindoline (20mg, 0.085 minol) and a carboxylic acid (0.102 rnmol) in DMF (1 mL) was treated with 1-[bis (dimethylamino)methylene] -1H-1, 2, 3-tr¡Àazolo[4, 5- b]pyridinium 3-oxid hexafluorophosphate (HATU; 39 mg, 0.102 mmol) and i-Pr2NEt (17 pL, 0.102 mmol) . The reaction was allowed to proceed overnight (about 18 hours), after which the solution was diluted with EtOAc (about20 mL) . The diluted reaction was extracted twice with saturated aq. NaHCO3 and once with saturated aq. NaC1. The organic layer was dried over Na2SO4. The products were purified by flash chromatography (SiC2) using an EtOAc/hexanes solvent gradient. Yield: 20.1 mg (78%), white solid, mixtureof rotamers. ?H NMR (600 MHz, ODd3) 7.75 – 7.55 (m,1H), 7.51 (s, 1H), 7.42 – 7.22 (m, 1H), 7.17 and 7.14(d, J = 8.2 Hz, 1H) , 7.05 – 6.92 (m, 1H) , 5.97 and5.95 (d, J = 1.7 Hz, 1H), 4.79 – 4.40 (m, 4H), 1.90(dd, J = 6.9, 1.7 Hz, 3H), 1.51 (s, 9H) . NMR (151MHz, ODd3) 164.2, 154.7, 141.8, 137.7, 125.5,123.2, 123.0, 119.4, 114.5, 79.9, 52.5, 52.2, 52.1,51.8, 28.7, 18.0. HRESI-TOF m/z 303.1702 (C,7H22N203 +H, required 303.1703)

The synthetic route of tert-Butyl 5-aminoisoindoline-2-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE SCRIPPS RESEARCH INSTITUTE; BOGER, Dale, L.; (104 pag.)WO2017/210206; (2017); A1;,
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Related Products of 5332-26-3, 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. 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of LiHMDS (31.3 mL, M in THF) in THF (40 mL) was added at -78C a solution of intermediate A.ii (6.50 g, 26 mmol) in THF (50 mL) over 10 min. After stirring for 1 h at -78C, a solution of N-(bromomethyl)phthalimide in THF (50 mL) was added dropwise over 10 min. The mixture was stirred at -78C for 1 h and then at rt overnight. The resulting solution was quenched with INHCl (260 mL) and extracted with DCM. The combined org. layers were washed with water, dried over MgSO4, concentrated and purified by CC (Hept/EA 1 :1). The resulting solid was triturated with EA to afford the title intermediate as a colourless solid (2.42 g, 23% yield). MS (ESI, m/z): 409.3 [M+H+].

The chemical industry reduces the impact on the environment during synthesis 2-(Bromomethyl)isoindoline-1,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; HUBSCHWERLEN, Christian; RITZ, Daniel; RUEEDI, Georg; SURIVET, Jean-Philippe; ZUMBRUNN ACKLIN, Cornelia; WO2010/41194; (2010); A1;,
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