Month: July 2021

Reference of 337536-15-9, 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. 337536-15-9, name is 4-Bromoisoindolin-1-one, This compound has unique chemical properties. The synthetic route is as follows.

Example 10 4-{5-[3-chloro-5-(trifluoromethoxy)phenyl]-1-(pyridine-3-yl)-1H-pyrazole-3-yl}-2,3-dihydro-1H-pyrrolo[3,4-c]pyridine-1-one Step 4 [0572] In four parallel procedures, four portions of 175 mg (0.42 mmol) of the product from step 3 are each dissolved in 5 ml dioxane and combined with 128 mg (0.50 mmol) of bis-pinakolato-diboron, 123 mg (1.26 mmol) potassium acetate and 21 mg (0.025 mmol) [1,1-bis-(diphenyl-phosphino)ferrocene]-dichloropalladium-dichloro-methane complex. Each reaction mixture is stirred in the microwave for 1 h at 120 C., cooled to RT, combined with 85 mg (0.50 mmol) of the compound from example 22A, 0.42 ml (2 N in water, 0.84 mmol) of a sodium carbonate solution and 17 mg (0.02 mmol) [1,1-bis-(diphenylphosphino)ferrocene]-dichloropalladium-dichloromethane complex and stirred for 2 h at 120 C. The reaction mixtures are combined. The suspension is diluted with acetonitrile, filtered through a Millipore filter and separated by preparative HPLC (solvent: acetonitrile/water gradient). Once the resulting solid has crystallized out of the acetonitrile, this produces 286 mg (36% of theoretical yield) of the title compound. Example 11 4-{5-[3-chloro-5-(trifluoromethoxy)phenyl]-1-(pyridine-3-yl)-1H-pyrazole-3-yl}-2,3-dihydro-1H-isoindole-1-one [0575] [0576] The synthesis of the title compound is performed starting from 100 mg (0.24 mmol) of the product from step 3 of the compound from example 10 in a manner analogous to step 4 of the synthesis of the compound from example 10. Instead of the compound from example 22A, 4-bromo-2,3-dihydroisoindole-1-on (61 mg, 0.29 mmol) is used. This produces 28 mg (24% of theoretical yield, 94% purity) of the title compound. [0577] 1H-NMR (400 MHz, DMSO-d6): delta=4.73 (s, 2H), 7.21 (s, 1H), 7.51-7.60 (m, 2H), 7.61-7.69 (m, 3H), 7.72 (d, 1H), 7.89 (d, 1H), 8.17 (d, 1H), 8.61-8.71 (m, 2H), 8.75 (s, 1H). [0578] LC-MS (Method 3): Rt=1.13 min; MS (ESIpos): m/z=471 [M+H]+.

The chemical industry reduces the impact on the environment during synthesis 4-Bromoisoindolin-1-one. I believe this compound will play a more active role in future production and life.

Reference:
Patent; AICURIS GMBH & CO. KG; Wildum, Steffen; Klenke, Burkhard; Wendt, Astrid; US2015/203500; (2015); A1;,
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Reference of 118289-55-7, A common heterocyclic compound, 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one, molecular formula is C10H9Cl2NO, 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.

EXAMPLE 3 2 moles of Piperazine Benzisothiazole hydrochloride, 1 mole of 5-(2-chloroethyl)-6-chlorooxindole in water (20 times based on benzisothiazole) and in the presence of dispersing agent. All the reactants are charged in to the flask and refluxed under nitrogen, under stirring for 12-16 hr. After the completion of the reaction, the reaction mass is cooled to room temperature and the resulting mass is filtered. It is slurried in IPA and then in water and isolated by filtration. The solid is dried at 95-100 C.Yield: 90-92%, Purity 98% (min).

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; ALKEM LABORATORIES LIMITED; US2011/3995; (2011); A1;,
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Application of 334952-09-9, 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. 334952-09-9, name is 2-Oxoindoline-6-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows.

2-carbonylindolone-6-carboxylic acid (40 g, 0.23 mol) was added to the reaction flask, 200 ml of methanol was added, and the mixture was slowly added dropwise, and the temperature was raised to 60 C by slowly dropping thionyl chloride (32 g, 0.27 mol). The reaction was carried out for 6 hours. After completion of the reaction, the reaction mixture was evaporated to dryness, ground with methanol, filtered and dried to obtain 40 g of 2-carbonylindolone-6-carboxylate in a yield of 93%.

The chemical industry reduces the impact on the environment during synthesis 2-Oxoindoline-6-carboxylic acid. I believe this compound will play a more active role in future production and life.

Reference:
Patent; (6 pag.)CN106854173; (2017); A;,
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400727-63-1, name is tert-Butyl 5-nitroisoindoline-2-carboxylate, 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: C13H16N2O4

To a solution of tert-butyl 5-nitroisoindoline-2-carboxylate (1.4) (3.8 g, 14.4 mmol) in MeOH (50 mL) was added 10% Pd/C (380 mg). The suspension was degassed under vacuum and purged with H2 several times. The mixture was stirred under H2 balloon at 50 C overnight. TLC showed the reaction was complete. The suspension was filtered through celite, which was washed three times with MeOH. The combined filtrate was concentrated and the residue was purified by column chromatography (eluted 50% EtOAc in hexanes) to afford tert-butyl 5- aminoisoindoline-2-carboxylate (1.5) (3.1 g, 92.2 %). [00327] LCMS: 235.3[M+1]+.

The synthetic route of 400727-63-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CELGENE AVILOMICS RESEARCH, INC.; SCHWARTZ, C., Eric; SURAPANENI, Sekhar, S.; WORM, Karin Irmgard; (266 pag.)WO2016/90079; (2016); A1;,
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Some common heterocyclic compound, 20870-79-5, name is 5-Nitroindolin-2-one, molecular formula is C8H6N2O3, 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. category: indolines-derivatives

To a suspension of 5-nitroindolin-2-one (2) (4 g, 22.5 mmol) in MeOH (200 mL) was added 10% Pd/C (0.2 g) under H2, and the mixture was stirred at 25 C for 24 h. Then the reaction mixture was filtered, and the filtrate was concentrated to give 4.5 g as a white solid. 1H NMR (400 MHz, DMSO-d6) delta: 9.90 (s, 1H), 6.51 (d, J = 2.0 Hz, 1H), 6.50 (d, J = 8.1 Hz, 1H), 6.38 (dd, J = 8.2, 2.2 Hz, 1H), 4.68 (s, 2H), 3.31 (s, 2H). 13C NMR (100 MHz, DMSO-d6) delta: 176.2, 143.6, 134.0, 126.9, 112.8, 112.0, 109.7, 36.5.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 20870-79-5, its application will become more common.

Reference:
Article; Han, Weina; Huang, Jian; Jiang, Jin; Ruhan, A.; Wang, Jinhui; Yao, Dahong; Bioorganic and medicinal chemistry letters; vol. 30; 17; (2020);,
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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 3335-98-6 as follows. Quality Control of 1-Phenyloxindole

General procedure: A mixture of isatins (1, 1.0 mmol), indolin-2-ones (2, 1.0 mmol) and ZrCl4 (23 mg, 0.1 mmol) was heated in anhydrous ethanol (5 mL) under reflux. After the disappearance of the reactants (8-12 h, monitored by TLC), the mixture was slowly cooled to room temperature. The red solids precipitated and were collected by filtration, then washed by a small amount of anhydrous ethanol to deliver pure compounds 3.

According to the analysis of related databases, 3335-98-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Liu, Meilin; Qiu, Shaozhong; Ye, Yu; Yin, Guodong; Tetrahedron Letters; vol. 57; 52; (2016); p. 5856 – 5858;,
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 1074-82-4 as follows. Safety of Potassium 1,3-dioxoisoindolin-2-ide

General procedure: To a solution of potassium 1,3-dioxoisoindolin-2-ide (1.85 g, 10.0 mmol), potassium iodide (0.08 g, 0.5 mmol) in acetone (25.0 mL), 1,2-dibromoethane dissolved in acetone (5.0 mL) was added by dropping funnel (3.72 g, 20.0 mmol), refluxed for 10 h. Monitored by TLC, and then filtered, concentrated by vacuum. The crude compound was purified by column chromatography on silica gel to give the desired intermediate 4 2-(2-bromoethyl) isoindoline-1,3-dione (1.83 g, 72.5% yield) as a white solid.

According to the analysis of related databases, 1074-82-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Xie, Ruliang; Mei, Xiangdong; Ning, Jun; Chemical and Pharmaceutical Bulletin; vol. 67; 4; (2019); p. 345 – 350;,
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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. 17630-75-0, name is 5-Chloro-2-oxindole, A new synthetic method of this compound is introduced below., Recommanded Product: 17630-75-0

General procedure: An oven-dried flask was charged with stir bar, oxindole (0.5 mmol), PIDA (0.25 mmol) in dry acetonitrile (4.0 mL). Then to the reaction mixture TEMPO (0.5 mmol) was added in presence of air and the mixture was stirred at room temperature until complete conversion takes place as indicated by TLC analysis. The resulting reaction mixture was extracted with ethyl acetate (3 10 mL). The combined organics were dried with Na2SO4 and dried under vacuum to afford crude solid. Then the crude product was purified by column chromatography on silica gel.

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; Sai Prathima, Parvathaneni; Bikshapathi, Raktani; Rao, Vaidya Jayathirtha; Tetrahedron Letters; vol. 56; 46; (2015); p. 6385 – 6388;,
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Related Products of 129487-92-9, A common heterocyclic compound, 129487-92-9, name is tert-Butyl 5-aminoindoline-1-carboxylate, molecular formula is C13H18N2O2, 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.

Compound 5-aminodihydroindole-1-carboxylic acid tert-butyl ester (200 mg, 0.77 mmol) and 4,6-dichloropyridazine-3-carboxylic acid methyl ester 1a (200 mg, 0.97 mmol) were dissolved in ethanol ( 10mL),It was then heated to 90 C in a sealed tube and stirred for 12 hours.After cooling to room temperature, the solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (petroleum ether / ethyl acetate = 1/1).The target product 5-((6-chloro-3- (methoxycarbonyl) pyridazin-4-yl) amino) dihydroindole-1-carboxylic acid tert-butyl ester 35a (200 mg, white solid) was obtained,Yield: 58%.

The synthetic route of 129487-92-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Beijing Nuochengjianhua Pharmaceutical Technology Co., Ltd.; Chen Xiangyang; Pang Yucheng; (142 pag.)CN110818641; (2020); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 20870-79-5, name is 5-Nitroindolin-2-one, molecular formula is C8H6N2O3, 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. Quality Control of 5-Nitroindolin-2-one

356 mg of 5-nitro-1,3-dihydro-indol-2-one is hydrogenated in 30 ml of tetrahydrofuran_ethanol=1:1 with 400 mg palladium on carbon (10%) at room temperature and normal pressure for 1 hour. After catalyst is suctioned off on diatomaceous earth and after concentration by evaporation, 320 mg (100% of theory) of 5-amino-1,3-dihydro-indol-2-one is obtained.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 20870-79-5, its application will become more common.

Reference:
Patent; Schering AG; US2004/39019; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem