Month: June 2021

Adding a certain compound to certain chemical reactions, such as: 24566-79-8, name is N-(6-Bromohexyl)phthalimide, 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 24566-79-8, Product Details of 24566-79-8

General procedure: Procedure M1. A mixture of the appropriate 2-(bromoalkyl)isoindoline-1,3-dione (1 equiv) with amine (pyrrolidine or morpholine) (1.1 equiv) in the presence of K2CO3 (3 equiv) was stirred in acetonitrile under reflux for 20 h. Subsequently, the solvent was evaporated under reduced pressure,producing a residue which was further dissolved in 20 mL of water and extracted with DCM(3 x 30 mL). The organic layer was dried with anhydrous Na2SO4. The solvent was then evaporated and the residue was purified by silica gel column chromatography (S3) yielding a yellow oil. The finalproduct was transformed into hydrochloride salt. The following compounds were obtained.

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, N-(6-Bromohexyl)phthalimide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Hebda, Michalina; Bajda, Marek; Wieckowska, Anna; Szal?aj, Natalia; Pasieka, Anna; Panek, Dawid; Gody?, Justyna; Wichur, Tomasz; Knez, Damijan; Gobec, Stanislav; Malawska, Barbara; Molecules; vol. 21; 4; (2016);,
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Reference of 21857-45-4, 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. 21857-45-4, name is 5-Methoxyindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 5-methoxyindoline (202 mg, 1.35 mmol) and N,N-diisopropylethylamine (0.34 mL, 2.0 mmol) in 4.0 mL of dry dichloromethane was added benzoyl chloride (0.23 mL, 2.0 mmol) at 0 C. After the reaction mixture was stirred at room temperature for 1 h, the reaction mixture was diluted with ethyl acetate. The solution was washed with saturated NaHCO3 aqueous solution, brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5 to 70/30) to obtain 5-methoxy-1-benzoylindoline (224 mg, 65%).

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, 5-Methoxyindoline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TOKYO INSTITUTE OF TECHNOLOGY; KYOTO UNIVERSITY; US2011/294850; (2011); A1;,
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Application of 3676-85-5,Some common heterocyclic compound, 3676-85-5, name is 5-Aminoisoindoline-1,3-dione, molecular formula is C8H6N2O2, 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.

Example 87 N’-(2-Aminobenzyl)-N’-(1,3-dioxo-2,3-dihydro-1H-5-isoindolyl)urea Palladium hydroxide (one small spatula) was added to a solution of the crystal (100 mg, 0.29 mmol) of the compound prepared in Example 86 (mixed with 4-aminophthalimide) in DMF, and the mixture was stirred under a hydrogen atmosphere at room temperature for 60min. After the completion of the reaction, the reaction solution was filtered through Celite, and washing with ethyl acetate was carried out. Water was then added to the filtrate, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and saturated brine and was dried over sodium sulfate. The solvent was then removed by distillation under the reduced pressure. Methanol was added to the residue, followed by filtration to give the title compound as a crystal (27 mg, 29.7%). MS m/z: 310 1H-NMR delta: 4.19 (2H, d, J = 5.37 Hz), 5.09 (2H, s), 6.52 (1H, t, J = 7.32 Hz), 6.63 (1H, d, J = 7.32 Hz), 6.72 (1H, t, J = 5.73 Hz), 6.97 (1H, dt, J = 1.46, 7.56 Hz), 7.04 (1H, d, J = 7.56 Hz), 7.59 (1H, dd, J = 1.95, 8.29 Hz), 7.67 (1H, d, J = 8.29 Hz), 8.01 (1H, d, J = 1.95 Hz), 9.28 (1H, s), 11.08 (1H, s)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Aminoisoindoline-1,3-dione, its application will become more common.

Reference:
Patent; KIRIN BEER KABUSHIKI KAISHA; EP1256574; (2002); A1;,
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 341988-36-1 as follows. Formula: C10H11NO2

To a solution of methyl indoline-6-carboxylate (600 mg, 3.40 mmol),1-(3-bromo-l-methyl- 6,7-dihydro-1N-pyrazolo[4,3-clpyridin-5(4H)-yl)ethanone (Intermediate B, 960 mg, 3.74 mmol), 2-dicyclohexylphosphino-2? ,6? -di-i-propoxy- I , 1? -biphenyl (158 mg, 0.34 mmol) andchloro(2-dicyclohexylphosphino-2?,6? -di-i-propoxy- 1,1? -biphenyl) [2-(2- aminoethylphenyl)]palladium(1l), methyl-tert-butylether adduct (277 mg, 0.34 mmol) in dioxane (10 mE) was added e-BuONa (976 mg, 10.20 mmol). The mixture was heated to 120°C for 16 h under a nitrogen atmosphere. After cooling the reaction to room temperature, water (20 mL) was added and the mixture was extracted with EtOAc (20 mE x 2). 1 M HC1(2 mL) was added to aqueous phase and then extracted with EtOAc (20 mL x 2), The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude residue was purified by reverse phase chromatography (acetonitrile 5-35percent / 0.1percent NH4HCO3 in water) to give the title compound (120 mg, 10percent) as a brown solid. ?HNMR (400 MHz, DMSO-d6) oe 7.58 (s, IH), 7.28 (d, J= 7.2 Hz, IH), 7.10 2H), 2.77 – 2.65 (m,2H), 2.08 – 2.06 (m, 3H). LCMS M/Z (M+H) 341.

According to the analysis of related databases, 341988-36-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; ROMERO, F. Anthony; MAGNUSON, Steven; PASTOR, Richard; TSUI, Vickie Hsiao-Wei; MURRAY, Jeremy; CRAWFORD, Terry; ALBRECHT, Brian, K.; COTE, Alexandre; TAYLOR, Alexander, M.; LAI, Kwong Wah; CHEN, Kevin, X.; BRONNER, Sarah; ADLER, Marc; EGEN, Jackson; LIAO, Jiangpeng; WANG, Fei; CYR, Patrick; ZHU, Bing-Yan; KAUDER, Steven; (0 pag.)WO2016/86200; (2016); A1;,
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Related Products of 897957-06-1, A common heterocyclic compound, 897957-06-1, name is 6-Bromo-1-methylindolin-2-one, molecular formula is C9H8BrNO, 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 1-3.2 (32.0 g, 142 mmol) in anhydrous dioxane (400 mL) is added R8 (S4.4 g, 241 mmol) andpotassium acetate ( 41.6 g, 424 mmol). The mixture is purged with Argon, [1 , 1’Bis(diphenylphosphino)ferrocene]dichloropalladium(IJ) as a complex with dichloromethane ( 11 .2g, 14 mmol) is added and the mixture is heated to 90 C for 2 h. The reaction mixture is diluted with ethyl acetate and water, the organic layer is washed with water, dried over MgS04 and concentrated. The residue is purified via flash chromatography (cyclohexane I EA = 70:30). Yield72%, m/z 274 [M+H]+, 11 0.67 min, LC-MS Method Y011_S01.

The synthetic route of 897957-06-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GRAUERT, Matthias; ANDERSKEWITZ, Ralf; GRUNDL, Marc; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; WO2014/140081; (2014); A1;,
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Application of 59-48-3, The chemical industry reduces the impact on the environment during synthesis 59-48-3, name is Indolin-2-one, I believe this compound will play a more active role in future production and life.

1,3-Dihydro-2H-indol-2-one (5.25 g, 39.43 mmol) (Aldrich) was treated with a 1:1 solution of glacial acetic acid and distilled water (246 mL). The resulting reaction mixture was cooled to 0 C and then slowly treated with N-bromosuccinimide (14.03 g, 78.85 mmol) (J.T. Baker). After the complete addition of N-bromosuccinimide, the cooling bath was removed, and the reaction mixture was stirred at 23 C for 1 h. Upon stirring at 23 C, the reaction mixture became viscous and a white solid precipitated. The reaction mixture was poured into 500 mL distilled water and filtered to provide a crude white solid. Recrystallization from methanol provided pure 5-bromo-1,3-dihydro-2H-indol-2-one as a light pink solid. (Yield 5.28 g, 63%; mp 219 – 220 C).

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, Indolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; EP1149092; (2003); B1;,
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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. 22190-33-6, name is 5-Bromoindoline, A new synthetic method of this compound is introduced below., name: 5-Bromoindoline

1,1-Dimethylethyl 5-bromo-2,3-dihvdro-1 H-indole-1-carboxylateTo a stirred solution of 5-bromo-2,3-dihydro-1 H-indole (30 g, 151 mmol) and DMAP (0.4 g, 3.27 mmol, 0.02 equiv) in 150 mL of MeCN at room temperature was added Boc20 (43 g, 197 mmol, 1.3 equiv) in one portion. The mixture was stirred at room temperature. After 10 min, the mixture gradually became a suspension. After 3 hours, the suspension was filtered. The cake was washed with cold MeCN (60 mL), and dried under house vacuum for 5 hours to give 1 ,1-Dimethylethyl 5-bromo-2,3-dihydro-1 H-indole-1- carboxylate (ca. 28.5 g prior to drying). LCMS (ES) m/z = 244, 242 as prominent fragments. 1 H NMR (400 MHz, DMSO-d6) delta ppm 1.50 (s, 9 H), 3.06 (t, J=8.7 Hz, 2 H),3.91 (t, J=8.7 Hz, 2 H), 7.31 (dd, J=8.5, 1.9 Hz, 1 H), 7.38 (s, 1 H), 7.51 – 7.71 (br s, 0.6 H).

The synthetic route of 22190-33-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; MEDINA, Jesus Raul; CHARNLEY, Adam Kenneth; ROMERIL, Stuart Paul; WO2015/56180; (2015); A1;,
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Electric Literature of 20780-72-7, A common heterocyclic compound, 20780-72-7, name is 4-Bromoisatin, molecular formula is C8H4BrNO2, 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.

Zinc powder (8.64 g, 132.13 mmol), titanium tetrachloride (12.60 g, 66.42 mmol) was added to THF (100 mL) and stirred at 80 C for 2 h, was added dropwise to the cooled 4-bromoisatin (5.01 g, 22.16 mmol) at room temperature under nitrogen protection THF (100 mL) was added.After the reaction was completed, hydrochloric acid (100 mL, 3M) was added, and the mixture was extracted with DCM (50 mL×3).The combined organic phases were washed with brine (50 mL × 2), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography to give compound 9a (2.63 g, 56.0%)

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; JACOBIO PHARMACEUTICALS CO., LTD; MA, CUNBO; GAO, PANLIANG; CHU, JIE; WU, XINPING; WEN, CHUNWEI; KANG, DI; BAI, JINLONG; PEI, XIAOYAN; (171 pag.)TW2019/25186; (2019); A;,
Indoline – Wikipedia,
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Some common heterocyclic compound, 20780-72-7, name is 4-Bromoisatin, molecular formula is C8H4BrNO2, 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 20780-72-7

9-Bromo-5H-[1,2,4]triazino[5,6-b]indole-3-thiol 5-Bromoisatin (1.0 g, 4.45 mmol), thiosemicarbizide (405 mg, 4.45 mg) and K2CO3 (920 mg, 6.67 mmol) were suspended in water (50 mL). The reaction mixture was stirred at reflux for 16 h over which time the dark brown suspension became a clear light brown solution. The solution was carefully acidified by dropwise addition of AcOH and resulting precipitate was filtered. The precipitate was recrystallised from DMF to yield a red solid (1.18 g, 95percent). deltaH (500 MHz, DMSO-d6, 363K) 7.43-7.52 (3H, m), 14.68 (1H, br s) deltaC (125 MHz, DMSO-d6) 113.0, 117.0, 118.3, 127.4, 133.5, 136.1, 145.3, 149.9, 180.0 mp>300° C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 20780-72-7, its application will become more common.

Reference:
Patent; Christou, Ivy; Cross, Rebecca Lillian; Gianella-Borradori, Matteo; Greaves, David Robert; Russell, Angela Jane; Wynne, Graham Michael; US2014/378451; (2014); A1;,
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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. 3783-77-5, name is 2-(3-Oxobutyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C12H11NO3

Synthesis of 2-(4-bromo-3-oxo-butyl)-isoindole-1 ,3-dione (C12H10NO3Br, MW = 294.98) To an ice-cooled and well-stirred suspension of 2-(3-oxo-butyl)-isoindole-1 ,3-dione (30.0 g, 138 mmol, 1 eq.) in MeOH (180 mL), bromine (14.3 mL, 276 mmol, 2 eq.) was added in one portion. The resulting red heterogeneous mixture was stirred at 0 C for 5 min., and further at r.t. for 3.5 hours. The orange homogeneous reaction mixture was then treated with 10M aq. H2SO4 soln. (26.2 mL). The resulting heterogeneous mixture was further stirred at r.t. for 2 hours. The resulting heterogeneous reaction mixture was filtered in order to isolate the target product as a white-off solid which was further dried under high vacuum. The product was used without further purification. LC-MS 3: tR = 0.76 min; [M+Hf = 296.1

According to the analysis of related databases, 3783-77-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; AISSAOUI, Hamed; BOSS, Christoph; RICHARD-BILDSTEIN, Sylvia; SIEGRIST, Romain; WO2014/6585; (2014); A1;,
Indoline – Wikipedia,
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