Month: January 2021

Adding a certain compound to certain chemical reactions, such as: 3676-85-5, name is 5-Aminoisoindoline-1,3-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 3676-85-5, category: indolines-derivatives

The synthesis of bromoacetal 6 from phthalimide (7) is shown in FIG. 11. Based on reactions described in the literature, these transformations were carried out on large scale, and some steps were improved. Nitration of 200 g of phthalimide (7) gives 146 g of 5-nitrophthalimide (8). Reduction of 8 by catalytic hydrogenation, according to the literature procedure, is a bottleneck in the synthesis because of the large volume of solvent needed. With a 2 L Parr hydrogenator pressure vessel, 30 g of 8 is converted to 25 g of amine 9. The next step is also a reduction; aminophthalide 10 is obtained quantitatively from 9 by copper-catalyzed reaction with zinc in aqueous base. Steps b and c could be combined by treating 8 with zinc dust and copper(II) sulfate in 2 M aq. sodium hydroxide. This variation, which is not shown in FIG. 11, removes the bottleneck, potentially allowing 100 g of 10 to be prepared in one step from 146 g of 9. The reaction conditions for the steps shown in FIG. 11 are as follows: a) HNO3, H2SO4, 0 C., 56% ; b) 5% Pd/C, H2, EtOAc, 97% ; c) Zn, CuSO4, 6 M NaOH, 5 C. then heated at 70-80 C. 16 h, 100% ; d) NaNO2, 4 M HBr, followed by CuBr at 0 C.; e) DIBAL, toluene, -42 C.; f) BF3 OEt2, MeOH, RT.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Aminoisoindoline-1,3-dione, and friends who are interested can also refer to it.

Reference:
Patent; Bell, Thomas W.; Cline, Joseph I.; Cremo, Christine R.; Gillett, Stephen L.; Frederick, John H.; US2011/77394; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 22190-33-6, A common heterocyclic compound, 22190-33-6, name is 5-Bromoindoline, molecular formula is C8H8BrN, 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 solution of 5-bromoindoline (3.3 g, 16.7 mmol) in DCM (33 mL) at room temperaturewas added 4-dimethylaminopyridine (0.21 g, 1.7 mmol), di-iso-propylethyl amine (4.3 g,33.4 mmol) and di-tert-butyldicarbonate (5.8 g, 26.7 mmol). The resulting mixture was stirred at room temperature for 16 h and then concentrated in vacuo. The crude residue was purified by silica gel chromatography (petroleum ether / EtOAc = 9: 1) to give the title compound (3.63 g, 73%) as a white solid.

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; 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;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 868066-91-5, name is 5-Bromo-2-methylisoindolin-1-one, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C9H8BrNO

Step B: 2-methyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)isoindolin-l-one [0236] 5-Bromo-2-methylisoindolin-l-one (0.112 g, 0.495 mmol), bis(pinacolato)diboron (0.189 g, 0.743 mmol), potassium acetate (0.146 g, 1.486 mmol), and PdCl2(dppf)CH2Cl2 adduct (0.020 g, 0.025 mmol) were suspended in DMA (1.0 mL). The mixture was degassed with N2 and heated in a sand bath at 100C overnight. The reaction mixture was subsequently cooled, diluted with EtOAc (10 mL), and passed through a syringe filter. The filtrate was diluted with water (10 mL) and the layers were separated. The aqueous layer was washed with EtOAc (2 x 5 mL). The organic layers were combined and concentrated in vacuo to give the title compound as a brown residue, which was used without further purification.

According to the analysis of related databases, 868066-91-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; LAWSON, John David; SABAT, Mark; SMITH, Christopher; WANG, Haixia; CHEN, Young K.; KANOUNI, Toufike; WO2013/148603; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 169037-23-4, A common heterocyclic compound, 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, molecular formula is C9H4F3NO3, 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: 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.

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; 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;,
Indoline – Wikipedia,
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. 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, A new synthetic method of this compound is introduced below., SDS of cas: 102359-00-2

To a solution of compound 1 (177 mg, 05 mmol) in Py (5 mL) was added EDCI (382 mg, 1 mmol) followed by amine tert-butyl 2-amino-4-(thiophen-2-yl)phenylcarbamate (260 mg, 0.9 eq). The mixture was stirred at rt overnight. The reaction was concentrated to get a residue, which was extracted with EA/water to get compound 2 (218 mg, 62%).

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; REGENACY PHARMACEUTICALS, LLC; VAN DUZER, John, H.; MAZITSCHEK, Ralph; BLUM, Charles; (70 pag.)WO2020/68950; (2020); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 19155-24-9, name is 3,3-Dimethylindolin-2-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. Formula: C10H11NO

Example 60; Preparation of Intermediate Compound 6OA; To a solution of compound 47C (0.30 g, 0.61 mmol) was added compound 5OA ( 98 mg, 0.61 mmol), CuI (58 mg, 0.31 mmol), K3PO4 (263 mg, 1.24 mmol), and 1 ,2-trans-diamino cyclohexane (73 muL, 0.61 mmol). The mixture was diluted with dioxane (4 mL) and degassed under house vacuum and filled with N2 six times. The reaction mixture was heated to 100 ¡ãC, stirred for 12 hours, cooled to rt, and concentrated under reduced pressure. The crude product was taken up in a 20:1 mixture of CH2CI2/MeOH (5 mL), filtered and concentrated under reduced pressure. The residue from the filtrate was purified using preparative thin-layer chromatography using a 3:1 mixture of hexanes/EtOAc as eluent to provide 125 mg EPO (36percent yield) of compound 6OA as an off-white solid. LC-MS [M+H] = 566.3; 98percent purity.

The synthetic route of 3,3-Dimethylindolin-2-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; WO2008/54749; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 2913-97-5, name is N-(2-Oxoethyl)phthalimide, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 2913-97-5

To a stirred solution of 9 (0.38mmol) in MeOH (2mL), NH4OAc (3.76mmol), 2-(1,3-dioxoisoindolin-2-yl)acetaldehyde (10) (0.56mmol), and MTBE (2mL) were added at room temperature. The mixture was heated at 50¡ãC for 10h and then cooled to room temperature. The pH of the reaction mixture was adjusted to 8 with saturated aqueous NaHCO3 solution. The reaction mixture was extracted with EtOAc (2¡Á35mL), and the combined organic layer was washed with water (10mL) and brine (10mL). The EtOAc solution was dried over anhydrous Na2SO4, filtered, and evaporated to dryness under reduced pressure. The residue was purified by MPLC on silica gel using MeOH/ CH2Cl2 (1:20) as eluent to give the titled compound as a yellow solid. Yield 67percent; mp 262?263¡ãC; IR (KBr) 3076, 2928, 1716, 1391cm?1; 1H NMR (400MHz, CDCl3/CD3OD) delta 2.51 (s, 3H), 5.00 (s, 2H), 7.00 (d, 1H, J=7.6Hz), 7.10 (d, 1H, J=8.0Hz), 7.42 (t, 1H, J=7.8Hz), 7.67 (d, 1H, J=9.2Hz), 7.69?7.72 (m, 2H), 7.74 (dd, 1H, J=9.2, 1.6Hz), 7.83?7.86 (m, 2H), 8.28 (s, 1H), 8.87 (br s, 1H); 13C NMR (100MHz, CDCl3) delta 24.6, 35.5, 116.3, 117.7, 122.2, 122.8, 123.9 (2C), 128.0, 128.9, 131.7, 132.1 (2C), 134.2, 134.6 (2C), 137.3, 143.3, 147.7, 150.0, 154.5, 159.1, 168.1 (2C); HRMS-ESI: m/z [M+H]+ calcd for C24H18N7O2: 436.1516, found 436.1530.

According to the analysis of related databases, 2913-97-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Jin, Cheng Hua; Krishnaiah, Maddeboina; Sreenu, Domalapally; Subrahmanyam, Vura Bala; Park, Hyun-Ju; Park, So-Jung; Sheen, Yhun Yhong; Kim, Dae-Kee; Bioorganic and Medicinal Chemistry; vol. 22; 9; (2014); p. 2724 – 2732;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 2058-74-4, name is 1-Methylisatin, 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 2058-74-4, Quality Control of 1-Methylisatin

General procedure: Sulfonated-b-cyclodextrin (b-CD-SO3H) (0.1 mmol) was dissolved in water(2 mL) at room temperature by stirring to get the clear solution. Then thereaction was shifted to reflux with addition of isatin (1 mmol) and indole(2 mmol) with constant stirring. The progress of the reaction was monitored byTLC. After completion of reaction, it was cooled to room temperature andfiltered, to get the solid. The crude product was recrystallized from aqueousethanol (60:40) giving pure 3,3-di(indolyl)indolin-2-ones.

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, 1-Methylisatin, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Tayade, Yogesh A.; Patil, Dipak R.; Wagh, Yogesh B.; Jangle, Asha D.; Dalal, Dipak S.; Tetrahedron Letters; vol. 56; 5; (2015); p. 666 – 673;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 611-09-6, name is 5-Nitroindoline-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 611-09-6, Safety of 5-Nitroindoline-2,3-dione

General procedure: A mixture of isatin derivatives (1a-1d, 1 mmol) oracenaphthoquinone (5, 1 mmol), methylene nitriles (2a,2b, 1 mmol), 1,3-dicarbonyl (3, 1 mmol), and 5 mg IG in3 cm3 H2O was stirred at 60 C for the mentioned timeshown in tables. Rapid conversion of reagents can beclearly confirmed by reaction color change. The progress ofthe reaction was monitored by TLC using EtOAc/n-hexane(1:3) as an eluent. Upon completion, the reaction mixturewas allowed to cool to room temperature and the precipitatewas obtained from the reaction mixture by filtration.The product 4a was dissolved in DMSO and the catalystwas separated by simple filtration. Pure products wereafforded by evaporation of the solvent under reduced pressure.

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-Nitroindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Javanshir, Shahrzad; Saghiran Pourshiri, Nassim; Dolatkhah, Zahra; Farhadnia, Mohammad; Monatshefte fur Chemie; vol. 148; 4; (2017); p. 703 – 710;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 193354-13-1, These common heterocyclic compound, 193354-13-1, name is 5-Iodoindolin-2-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-Methoxycarbonyl-2-oxindole 5-Iodo-2-oxindole (17 g) was refluxed with 2 g of palladium diacetate, 18.2 g of triethylamine, 150 mL of methanol, 15 mL of dimethylsulfoxide and 2.6 g of DPPP in an atmosphere saturated with carbon monoxide. After 24 hours, the reaction was filtered to remove the catalyst and the filtrate concentrated. The concentrate was chromatographed on silica gel (30% ethyl acetate in hexane). The fractions containing product were concentrated and allowed to stand. The precipitated product was collected by vacuum filtration to give 0.8 g (7%) of the title compound as an off-white solid.

Statistics shows that 5-Iodoindolin-2-one is playing an increasingly important role. we look forward to future research findings about 193354-13-1.

Reference:
Patent; Sugen, Inc.; US6486185; (2002); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem