Author: tianli

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. 71294-03-6, name is 7-Fluoroindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 7-Fluoroindolin-2-one

7-Fluoro-1,3-dihydro-indol-2-one (7.3 g, 48 mmol) and lithium chloride (6.67 g, 158 mmol) were dissolved in tetrahydrofuran (200 mL). The solution was cooled to -78 C. and n-butyllithium (40 mL, 100 mmol) was added slowly over a 15 minute period. After 20 minutes at -78 C., methyl iodide (6 mL, 96 mmol) was added and the mixture allowed to warm to room temperature. After 24 hours, the mixture was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and concentrated in vacuo. The crude product was purified via Biotage chromatography (Flash40i, silica, 10% then 20% ethyl acetate/hexane) gave 4.1 g (48%) 7-fluoro-3,3-dimethyl-1,3-dihydro-2H-indol-2-one. MS (ESI) m/z 180, [M+H]+).

According to the analysis of related databases, 71294-03-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wyeth; US2007/72928; (2007); A1;,
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Some common heterocyclic compound, 7477-63-6, name is 7-Chloroisatin, 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 7-Chloroisatin

7-Chloroisatin 1a (0.5 mmol, 90.6 mg), CuI (10 molpercent, 9.5 mg) was added to a 15-mL thick-walled pressure tube, 1,10-phenanthroline(10 molpercent, 9.0 mg) and ethyl isocyanoacetate 2 (0.6 mmol, 67.2 mg) were added, and 2 mL of toluene was added as the solvent The oil bath was 110 ¡ã C and the reaction was followed by TLC until the reaction was complete. After the end of the reaction, stop heating, transfer to a single mouth bottle spin, with PE: EA = 4: 1 column chromatography gave the product as a yellow solid which was identified as 7-chloro-3-methyleneindolone 3a by NMR and HRMS. The yield was 75percent.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7477-63-6, its application will become more common.

Reference:
Patent; Qingdao University of Science and Technology; Li, Ming; Yu, Le; Wen, Lirong; (14 pag.)CN106083690; (2016); A;,
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Application of 2058-72-2,Some common heterocyclic compound, 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-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.

General procedure: To a stirred mixture of 1-benzyl-1H-indole-2,3-dione (1a, 0.25 g,1.05 mmol), CuI (0.01 g, 0.05 mmol, 0.05 equiv), and phenylacetylene (2a, 0.11 g, 1.11 mmol, 1.05 equiv) in anhyd toluene (2 mL), DBU (0.032 g, 0.21 mmol, 0.2 equiv) was added at 25 C under a N2 atmosphere. Stirring was continued at this temperature until the starting material was completely consumed (TLC monitoring). After completion, the mixture was quenched with sat. aq NH4Cl (2mL) and extracted with EtOAc (2 ¡Á 5 mL). The combined organic layers were dried (anhyd Na2SO4) and evaporated under reduced pressure to dryness. The crude product thus obtained was purified by column chromatography (activated silica gel, 60-120 mesh, hexane-EtOAc) to afford pure 3aa as a white solid; yield: 0.35 g (97%); mp 177-179 C.

The synthetic route of 2058-72-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chouhan, Mangilal; Senwar, Kishna Ram; Kumar, Kapil; Sharma, Ratnesh; Nair, Vipin A.; Synthesis; vol. 46; 2; (2014); p. 195 – 202;,
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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 99365-40-9 as follows. Formula: C8H6BrNO

Under an argon atmosphere NaH (60 % on mineral oil, 7.32 g) was suspended in dry THF (45 ml). A suspension of 6-bromoindolin-2-one (10.0 g) in dry THF (108 ml) was added in portions during 10 min keeping the temperature below 27 C. The reaction mixture was warmed to 25 C, Mel (11.4 ml) was added drop wise during 1 h while the internal temperature was carefully kept between 24 and 27 C and stirring was continued for 18 h. Saturated aqueous NH4C1 solution (20 ml) was carefully added at 10-15 C, the mixture was diluted with EtOAc and saturated aqueous NaHC03 solution, the organic layer was washed with saturated aqueous NaHC03 solution, dried and evaporated. The residue was purified by flash chromatography (siliga gel, gradient 0% to 30% EtOAc in n-heptane) to give the title compound (10.1 g, 84%) as a light red solid. MS (ESI, m/z): 254.1/256.2 [(M+H)+].

According to the analysis of related databases, 99365-40-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HILPERT, Hans; KOLCZEWSKI, Sabine; LIMBERG, Anja; STOLL, Theodor; WO2015/177110; (2015); A1;,
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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 169037-23-4 as follows. Formula: C9H4F3NO3

General procedure: A mixture of indoline-2,3-dione 1 (1mmol), l-tryptophan (2a) or l-histidine 2b (1mmol) and (E)-(2-nitrovinyl)benzene 3 (1.1mmol) was heated while stirred in [bmim]Br as the reaction medium (3mL) for 1hat 100C. After completion of the reaction (TLC), EtOAc (5mL) was added and the reaction mixture was stirred for 10min. This treatment was repeated and the combined ethyl acetate layers were removed in vacuo. The crude product was purified by recrystallization of the residue from EtOH (compounds 4) or by column chromatography (compounds 5). After extraction of the product, the ionic liquid was dried under vacuum at 80C for 2h to eliminate any water and could be reused for subsequent runs of the reaction.

According to the analysis of related databases, 169037-23-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Arumugam, Natarajan; Almansour, Abdulrahman I.; Kumar, Raju Suresh; Periasamy, Vaiyapuri Subbarayan; Athinarayanan, Jegan; Alshatwi, Ali A.; Govindasami, Periyasami; Altaf, Mohammad; Menendez, J. Carlos; Tetrahedron; vol. 74; 38; (2018); p. 5358 – 5366;,
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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 20870-79-5 as follows. SDS of cas: 20870-79-5

5-Amino-2-oxindole 5-Nitro-2-oxindole (6.3 g) was hydrogenated in methanol over 10% palladium on carbon to give 3.0 g (60% yield) of the title compound as a white solid.

According to the analysis of related databases, 20870-79-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sugen, Inc.; US6486185; (2002); B1;; ; Patent; Sugen, Inc.; US6114371; (2000); A;,
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Reference of 356068-93-4,Some common heterocyclic compound, 356068-93-4, name is (Z)-5-((5-Fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid, molecular formula is C16H13FN2O3, 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 8d. (?)-Methyl 3-(4-(2-(5-((Z)-(5-fluoro-2-oxoindolin-3-ylidene)methyl)-2,4- dimethyl -lH-pyrrole-3-carboxamido)ethoxy)phenyl)acrylate (Compound 304) To a stirred solution of compound 109 (0.5 g, 1.67 mmol) in DMF( 40 mL) at00C was added etaOBt (0.34 g, 2.5 mmol), triethylamine (0.94 mL, 6.68 mmol), ECDI-HCl (0.48 g, 2.5 mmol) and compound 303 (0.44 g, 2.0 mmol) successively. The mixture was stirred overnight at room temperature, evaporated, diluted with water (50 mL), brine (50 mL) and saturated aqueous sodium bicarbonate(50 mL). The pH of solution was adjusted to 11-12 with 1OM NaOH. The mixture was filtered, washed with water, dried to obtain desired product 304 as a yellow solid (630 mg, 75%). LCMS: 504 [M+l]+, 1H NMR (DMSO-^6): delta 2.39 (s, 3H), 2.41 (s, 3H), 3.59 (m, 2H), 3.69 (s, 3H), 4.15 (t, J= 4.5 Hz, 2H), 6.45 (d, IH), 6.94 (m, 4H), 7.65 (m, 6H), 10.87 (s, IH), 13.66 (s, IH).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (Z)-5-((5-Fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid, its application will become more common.

Reference:
Patent; CURIS, INC.; WO2008/33743; (2008); A1;,
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Related Products of 52351-75-4, 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. 52351-75-4 name is 6-Methoxyindoline-2,3-dione, 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.

Intermediate- 136: 6-Methoxy-l-methylindoline-2, 3-dione:To a stirred suspension of commercially available 6-methoxyindoline-2,3-dione (0.2 g ,1.12 mmol) and sodium hydride (60% w/w dispersion in mineral oil, 0.067 g,2.79 mmol) in dry DMF ( 5 ml) was added methyl iodide (0.084 ml, 1.35 mmol) slowly at 0 C. The mixture was stirred at 0 C for 45 min and quenched with water (10 ml) at 0 C and added ethyl acetate. The two phases were separated and the aqueous phase was extracted with ethyl acetate (2x 25 ml). The combined organic layer was washed with water (2×20 ml), followed by brine (2×20 ml), dried over sodium sulfate and filtered. The filtrate was concentrated in vacuum to dryness to get a brown solid of 6-methoxy-l-methylindoline-2, 3-dione (0.140 g, 65%). 1H NMR (400 MHz, CDC13) delta 7.58 (d, J = 8 Hz, 1H), 6.57 (dd, J = 8 Hz, 4 Hz, 1H), 6.36 (d, J = 4 Hz, 1H), 3.93 (s, 3H), 3.22 (s, 3H); MS (ES+) m/z 191.9 (M+l), 213.9 (M+ Na)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Methoxyindoline-2,3-dione, and friends who are interested can also refer to it.

Reference:
Patent; LUPIN LIMITED; PADIYA, Kamlesh, Jyotindra; NAIR, Prathap, S.; PAL, Ravindra, Ramsurat; CHAURE, Ganesh, Shankar; GUDADE, Ganesh, Bhausaheb; PARKALE, Santosh, Sadashiv; MANOJKUMAR, Vishwanath, Lohar; SWAPNIL, Ramesh, Bajare; SMITA, Aditya, Bhoskar; SACHIN, Dilip, Survase; PALLE, Venkata, P.; KAMBOJ, Rajender, Kumar; WO2012/49555; (2012); A1;,
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Reference of 16078-34-5, A common heterocyclic compound, 16078-34-5, name is 1-(2,3-Dihydro-1H-indol-5-yl)-ethanone, molecular formula is C10H11NO, 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: RuCl3nH2O (0.5 mol %), HMTA-Bz (1 mol %), amine (0.25 ml)and dry toluene (1.0 ml) were placed in a Schlenk tube. The reactionmixture was stirred under open condition to nitrogen andrefluxed for 24 h. After completion of the reaction all toluene wereevaporated under vacuo, the oxidized products were isolated fromcrude mixture with the help of column chromatography using hexane/EtOAc as eluent. The formation of products was confirmed bycomparing the 1H NMR data with literature reports.

The synthetic route of 16078-34-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Barteja, Parul; Devi, Preeti; Kannan, Muthukumar; Muthaiah, Senthilkumar; Journal of Catalysis; vol. 386; (2020); p. 1 – 11;,
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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. 6326-79-0, name is 6-Bromoisatin, A new synthetic method of this compound is introduced below., Recommanded Product: 6326-79-0

Step 1: Synthesis of Intermediate 1-12.1 To R27 (25.0 g, 111 mmol) in acetonitrile (750 mL) is added Mel (15 niL, 241 mmol) and K2C03 (60.0 g, 434 mmol) and the reaction mixture is stirred at 60 C for 2 h. The reaction mixture is filtered and concentrated. Water and ethyl acetate are added to the residue. The organic layer is extracted twice with water, dried over MgS04 and concentrated. Yield 56%, m/z 240/242 [M+H]+, rt 0.48 min, LC-MS Method X001 004.

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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ANDERSKEWITZ, Ralf; GRAUERT, Matthias; GRUNDL, Marc; HAEBEL, Peter, Wilhelm; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; BINDER, Florian; VINTONYAK, Viktor; WO2014/140075; (2014); A1;,
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