Indolines-derivatives

Application of 1035235-27-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 1035235-27-8 name is tert-Butyl 4-bromoisoindoline-2-carboxylate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Example 136 r(S)-1-(2.4-Difluoro-3-phenoxy-phenyl)-propy|1-(2,3-dihydro-1 H-isoindol-4-yl)-am hydrochlorideStep 1 A solution of Key Intermediate 1 (50 mg, 0.19 mmol), fe -butyl 4- bromoisoindoline-2-carboxylate (57 mg, 0.19 mmol) and sodium fe -butoxide (26 mg, 0.27 mmol) in dioxane (1 ml) was degassed by bubbling through nitrogen for 5 mins. Tris(dibenzylideneacetone)dipalladium (0) (5 mg) and 2,2′-bis(diphenylphosphino)-1 ,1 ‘- binapthyl (5 mg) were added and the reaction mixture was heated to 120 C for 20 mins under microwave irradiation. The mixture was partitioned between sat. sodium hydrogen carbonate and ethyl acetate. The organic fractions were washed with brine, dried over magnesium sulfate, filtered and concentrated. The residue was purified by preparative hplc to give 4-[(S)-1-(2,4-difluoro-3-phenoxy-phenyl)-propylamino]-1 ,3-dihydro-isoindole-2- carboxylic acid tert-butyl ester (23 mg) as a solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl 4-bromoisoindoline-2-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; WOODHEAD, Andrew, James; CHESSARI, Gianni; BESONG, Gilbert, Ebai; CARR, Maria, Grazia; HISCOCK, Steven, Douglas; O’BRIEN, Michael, Alistair; REES, David, Charles; SAALAU-BETHELL, Susanne, Maria; WILLEMS, Hendrika, Maria, Gerarda; THOMPSON, Neil, Thomas; WO2013/64538; (2013); A1;,
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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. 875003-43-3, name is 7-Fluoro-1-methylindoline-2,3-dione, A new synthetic method of this compound is introduced below., Formula: C9H6FNO2

Step 2: Preparation of 7-fluoro-1-methyl-1,3-dihydro-indol-2-one 7-Fluoro-1-methyl-1H-indole-2,3-dione (Step 1, 1.05 g, 5.86 mmol) is heated with neat hydrazine hydrate (10 ml) at 130 C. for 1 hour. The mixture is cooled, diluted with ice water and extracted with ethyl acetate. The extract is washed with brine, dried (Na2SO4), and evaporated to give the title compound as a light yellow solid. HPLC r.t. 4.07 min; MS for C9H8FNO m/z 165.16 (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; Luehr, Gary W.; Jain, Rama; Renslo, Adam; Josyula, Vara Prasad Venkata Nagendra; Gordeev, Mikhail F.; US2006/30609; (2006); A1;,
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Adding a certain compound to certain chemical reactions, such as: 52351-75-4, name is 6-Methoxyindoline-2,3-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 52351-75-4, Application In Synthesis of 6-Methoxyindoline-2,3-dione

Step 3: Preparation of 7-methoxy-2-phenyl-quinoline-4-carboxylic acid 112.Compound 111 (500 mg, 1 eq.) and acetophenone (380 muL, 1.2 eq.) were added at room temperature to a solution of KOH (520 mg, 3.3 eq.) in ethanol (5 mL). The reaction mixture was stirred at 70 0C for 7 hrs. The mixture was then poured into ice/water, and washed with dichloromethane. Aqueous layer was acidified with 3N HCl to pH 2-3. The precipitate obtained was filtered, washed with water, and triturated in ethanol to yield compound 112 as a beige solid in 40% yield. MS (ESI, EI+): m/z = 280 (MH+).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; IDENIX PHARMACEUTICALS, INC.; WO2009/14730; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 611-09-6, name is 5-Nitroindoline-2,3-dione, molecular formula is C8H4N2O4, 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 611-09-6

General procedure: A mixture of isatins 1a-f (1 mmol), active cyanomethanes 2a-b (1 mmol), and enolizable ketones 3a-d (1 mmol) in ethanol (3 ml)was stirred at room temperature in the presence of HIL (Scheme 2).The reaction progress was monitored by thin-layer chromatography (TLC). After completion of the reaction, the reaction mixture was treated with ethanol to recover the insoluble catalyst by filtration.The filtrate was then concentrated under vacuum and the desired product was obtained. The structures of the products were confirmed by 1H NMR, IR spectroscopy, and supported by elemental analysis. The filtered catalyst was dried under vacuum for 2 h and was reused with a fresh charge of solvent and reactants for subsequent runs under the same reaction conditions to observe its catalytic efficiency.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 611-09-6, its application will become more common.

Reference:
Article; Satasia, Shailesh P.; Kalaria, Piyush N.; Avalani, Jemin R.; Raval, Dipak K.; Tetrahedron; vol. 70; 35; (2014); p. 5763 – 5767;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 340702-10-5, A common heterocyclic compound, 340702-10-5, name is 6-Fluoroisoindolin-1-one, molecular formula is C8H6FNO, 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 a stirred solution of 6-fluoroisoindolin-1-one (10 g, 66.2 mmol) in anhydrous dichloromethane (100 mL) were added triethylamine (16.72, 165.5 mmol, 21.8 mL), (Boc)2O (17.3 g, 79.4 mmol) and catalytic DMAP (100 mg) at room temperature. The reaction mixture was stirred at room temperature for 16 h. After completion, the reaction mixture was diluted with CH2Cl2, washed with H2O, and then saturated aqueous NaHCO3. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The crude compound was purified by silica gel chromatography (0-30% ethyl acetate in hexanes) to give the product. MS: (ES) m/z calculated for C13H14FNO3 [M+H]+ 252.3, found 252.3.

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; CHEMOCENTRYX, INC.; CHEN, Xi; DRAGOLI, Dean R.; FAN, Junfa; KALISIAK, Jaroslaw; LELETI, Manmohan Reddy; MALATHONG, Viengkham; McMahon, Jeffrey; TANAKA, Hiroko; YANG, Ju; YU, Chao; ZHANG, Penglie; Mali, Venkat; (62 pag.)US2017/144996; (2017); 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. 7477-63-6, name is 7-Chloroisatin, A new synthetic method of this compound is introduced below., Application In Synthesis of 7-Chloroisatin

The specific steps are:Add 7-chloroindole (54.5 mg, 0.3 mmol) to the pressure tube.Benzamidine hydrochloride (140.9 mg, 0.9 mmol),CuI (5.7 mg, 0.03 mmol)And potassium phosphate (381.6 mg, 1.8 mmol).Add 3mL of DMSO,After magnetic stirring at room temperature for 5 hours,The reaction solution was extracted with dichloromethane.The organic layer was washed with saturated brine.After drying anhydrous sodium sulfate,The solvent is distilled off under reduced pressure to obtain a crude product.The crude product is purified by column chromatography with dichloromethane/petroleum ether=1:20 (V/V) as the eluent to obtain the desired product. The product is a yellow solid.The yield was 68percent.

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; Wuhan Institute of Technology; Jia Fengcheng; Chen Yunfeng; (8 pag.)CN108558782; (2018); A;,
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Synthetic Route of 552330-86-6, These common heterocyclic compound, 552330-86-6, name is 5-Bromoisoindolin-1-one, 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.

5-Bromo-2,3-dihydro-lH-isoindol-l-one (100 mg, 0.47 mmol) was dissolved in DMF (4.7 mL) and stirred at 0C. NaH (38 mg, 0.94 mmol, 60 wt.% dispersion in oil) was carefully added in two portions, and the resulting mixture was allowed to stir at 0C for 15 minutes before 2,2,2-trifluoroethyl trifluoromethanesulfonate (110 mg, 0.47 mmol) was added. The mixture was allowed to stir at 0C for 30 minutes before saturated aqueous NaHC03 (10 mL) was carefully added, and the mixture was extracted with EtOAc. The organic layer was washed with water, brine, dried over anhydrous MgS04, filtered, and concentrated in vacuo. The residue was purified by silica chromatography, eluting with a 0-20% EtOAc/hexanes gradient. LRMS (ESI) calc’d for Ci0H8BrF3NO [M+H]+: 294, found: 294.

Statistics shows that 5-Bromoisoindolin-1-one is playing an increasingly important role. we look forward to future research findings about 552330-86-6.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DINSMORE, Christopher; FULLER, Peter; GUERIN, David; THOMPSON, Christopher F.; PU, Qinglin; SCOTT, Mark E.; KATZ, Jason David; KURUKLASURIYA, Ravi; CLOSE, Joshua T.; FALCONE, Danielle; BRUBAKER, Jason; ZENG, Hongbo; BAI, Yunfeng; FU, Jianmin; KONG, Norman; LIU, Yumei; ZHENG, Zhixiang; WO2014/146492; (2014); A1;,
Indoline – Wikipedia,
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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 17564-64-6 as follows. COA of Formula: C9H6ClNO2

General procedure: The initial carbonyl compound (50 mmol) was dissolved/suspended in ethanol (50 mL) and magnetically stirred with thiosemicarbazide (50 mmol) and catalytic amounts of acetic acid for 8-24 h at room temperature. The obtained thiosemicarbazone was filtered, washed with appropriate solvent (n-hexane, petroleumether or diethyl ether) and dried under vacuum. The intermediate thiosemicarbazone (50 mmol) reacted with ethyl bromoacetate (50 mmol), in methanol (50 mL) and sodium acetate (50 mmol) at room temperature under magnetic stirring for 24 h. The resulting 4-thiazolidinone was poured on ice, filtered or extracted with chloroform (3 x 100 mL) and purified by column chromatography (SiO2, ethyl acetate/n-hexane). Then, the obtained thiazolidinone (50 mmol) was dissolved/suspended in 50 mL of anhydrous acetone in the presence of anhydrous potassium carbonate (50 mmol), and reacted with equimolar amounts of 4-nitrobenzyl bromide, 1-(chloromethyl)naphthalene and N-(chloromethyl)phthalimide for 24-48 h. The product was poured on ice, filtered or extracted with chloroform (3 x 50 mL) and purified by column chromatography (SiO2, ethyl acetate/n-hexane) in order to obtain the title compoundsin high yields. 7.1.62 2-((2-(2-Cyclopentylidenehydrazono)-4-oxothiazolidin-3-yl)methyl)isoindoline-1,3-dione (10C) Pink powder, mp 169-175 C, 85% yield; 1H NMR (400 MHz, DMSO-d6): delta 1.62 (bs, 4H, cyclopentane), 2.15 (bs, 2H, cyclopentane), 2.29 (bs, 2H, cyclopentane), 3.98 (s, 2H, CH2, thiazolidinone), 5.51 (s, 2H, ArCH2), 7.84-7.93 (m, 4H, Ar).

According to the analysis of related databases, 17564-64-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; De Monte, Celeste; Carradori, Simone; Bizzarri, Bruna; Bolasco, Adriana; Caprara, Federica; Mollica, Adriano; Rivanera, Daniela; Mari, Emanuela; Zicari, Alessandra; Akdemir, Atilla; Secci, Daniela; European Journal of Medicinal Chemistry; vol. 107; (2016); p. 82 – 96;,
Indoline – Wikipedia,
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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. 334952-09-9, name is 2-Oxoindoline-6-carboxylic acid belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 2-Oxoindoline-6-carboxylic acid

8. 2-oxoindoline-6-carboxylic acid (1 equivalent), 3-((5-(formylfuran-2-yl)methylene)-N-acetyl-2-oxoindoline (1.2 equivalents) and piperidine (0.2 equivalent) were dissolved in ethanol such that 1 mL of ethanol was used per 1 mumol of the total amount of the compounds, and the resulting mixture was stirred at room temperature for 2 hours. After completion of the reaction, the resulting precipitate was collected by filtration, washed with cooled ethanol several times and dried, whereby (3E)-3-((5-((E)-(1-acetyl-2- oxoindolin-3-ylidene)methyl)furan-2-yl)methylene)-2-oxoindoline-6-carboxylic acid (6) was obtained. 1H-NMR (d6-DMSO, 400 Mz): 10.72 (s, br, 1H), 8.77 (s, 1H), 8.40 (d, J= 3.91 Hz, 1H), 8.25 (m, 1H), 8.03 (s, 1H), 8.17 (t, J= 7.81 Hz, 1H), 7.90 (s, 1H), 7.71 (s, 1H), 7.65 (d, J= 3.91 Hz, 1H), 7.63 (d, J= 7.80 Hz, 1H), 7.60 (d, J= 7.80 Hz, 1H), 7.11 (d, J= 7.80 Hz, 1H), 6.88 (t, J= 7.81 Hz, 1H), 2.66 (s, 3H), MS m/z: 440(M)+

The synthetic route of 334952-09-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Theravalues Corporation; EP2130829; (2009); 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. 446292-08-6, name is (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 446292-08-6

Methylamine (40% strength, 153.2 ml) was added to suspension of 2-({(5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)-1H-isoindole-1,3(2H)-dione (150 gm) in methanol (1500 ml) at 25 to 30 C. The reaction mass was refluxed for 6 hr, cooled to 25-30 C., followed by slow addition of acetic acid (300 ml) reaction mass. Thereaction mass was stirred for 30 min at 25-30 C. pH of the reaction mass was adjusted to 2-3 using conc. HCl. Reaction mass was stirred for 1 hr & filtered off the solid. The solid obtained was washed with methanol (50 ml) Obtained solid dissolved in mixture of methanol (500 ml) and methylene dichloride (750 ml) by adjusting pH of reaction mass to 7-8 using triethylamine at 25-30 C. and stirred till clear solution was obtained, then adjusted the pH of reaction mass to 4-5 by using acetic acid at 25-30 C. Reaction mass was stirred for 1 h at 25-30 C. and filtered off the solid. The solid obtained was washed with methanol (50 ml) and dried under vacuum at 50 to 55 C. for 5 hr to obtain 4-{4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one hydrochloride. [Yield=92.4 gm (80%); Purity (HPLC)=98.0%]

According to the analysis of related databases, 446292-08-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Mathad, Vijayavitthal Thippannachar; Patil, Nilesh Sudhir; Niphade, Navnath Chintaman; Mali, Anil Chaturlal; Bodake, Mahendra Bhagirath; Ippar, Sharad Subhash; Talla, Rajesh; US2015/11756; (2015); A1;,
Indoline – Wikipedia,
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