Author: Jessica.F

Synthetic Route of 264916-06-5, 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. 264916-06-5, name is tert-Butyl 5-aminoisoindoline-2-carboxylate belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Step-1: tert-butyl 5-((2-ethyl-1-(6-(2-hydroxypropan-2-yl)pyridin-2-yl)-3-oxo-2,3-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)amino)isoindoline-2-carboxylate To a stirred solution of 2-ethyl-1-(6-(2-hydroxypropan-2-yl)pyridin-2-yl)-6-(methylthio)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one (0.2 g 0.5790 mmol, 1.0 eq) in (5.0 mL) of toluene was added m-CPBA (0.280 g, 1.158 mmol, 2 eq) and allowed to stir at rt for 30 min. followed by addition of tert-butyl 5-aminoisoindoline-2-carboxylate (0.176 g, 0.7527 mmol, 1.3 eq) and DIPEA (0.3 ml 1.737 mmol, 3.0 eq) and allowed to stir at rt for overnight. The reaction mixture was diluted with water (20 mL) and extracted with EtOAc (2*20 mL). The combined organic layers were washed with water (30 mL), brine (30 mL), dried over Na2SO4, concentrated and purified by combi flash [silica gel-100-200 mesh; elution 0-35% EtOAc in Hexane] to afford the desired compound, tert-butyl 5-((2-ethyl-1-(6-(2-hydroxypropan-2-yl)pyridin-2-yl)-3-oxo-2,3-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)amino)isoindoline-2-carboxylate (0.100 g, 49.52%) as white solid.

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, tert-Butyl 5-aminoisoindoline-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; giraFpharma LLC; Chakravarty, Sarvajit; PHAM, Son Minh; Kankanala, Jayakanth; AGARWAL, Anil Kumar; PUJALA, Brahmam; SONI, Sanjeev; ARYA, Satish K.; PALVE, Deepak; Gupta, Ashu; KUMAR, Varun; (498 pag.)US2019/106427; (2019); 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. 16800-68-3, name is 1-Acetylindolin-3-one, This compound has unique chemical properties. The synthetic route is as follows., Formula: C10H9NO2

General procedure: 1a (35.0 mg, 0.2 mmol, 1 equiv.), tert-BuOK (22.4 mg, 0.2 mmol, 1.0 equiv.) were added to a Schlenk tube. Then 2 ml THF was added using a syringe. The reaction mixture was stirred 15min,and then added iodonium salt 2 (0.2 mmol, 1.0 eq). The reaction was stirred at 30C for 10 hours.After cooling to room temperature, the solvent was removed in vacuo and the residue was purifiedby silica gel using a proper eluent (EtOAc/Hexane) to afford the desired products

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 16800-68-3.

Reference:
Article; Zhang, Yanxia; Han, Jianwei; Liu, Zhen-Jiang; Synlett; vol. 26; 18; (2015); p. 2593 – 2597;,
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. 446292-08-6, name is (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Recommanded Product: 446292-08-6

Purification of intermediate compound of formula III using DMF and acetone50g of crude compound of formula III and 125 ml DMF were charged into a clean and dry 4 neck R.B.flask and heated to about 90C, the clear solution obtained, carbon (5g) was charged. The reaction suspension was stirred for 5 mins and filtered under hot conditions. The filtrate was cooled to about 30C, 150 ml of acetone was added and the solid separated was filtered after 30-45 min and washed with acetone(50ml) to afford 42.5g of pure product as half white colored solid.

The synthetic route of 446292-08-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SYMED LABS LIMITED; MOHAN RAO, dodda; KRISHNA REDDY, pingili; ANNA REDDY, ambati; VENKAT REDDY, buthukuri; WO2012/32533; (2012); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 41663-84-7, 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. 41663-84-7, name is 2-Methyl-5-nitroisoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 3 To a reaction vessel containing dimethylacetamide (25 ml) were added 4-nitro-N-methylphthalimide (0.51 g, 0.00248 mol), biphenyl (0.21 g, 0.00139 mol), sodium hydrogen sulfide (0.14 g, 0.00125 mol) and triethylamine (0.2 ml, 0.0014 mol). The reaction was allowed to proceed at 70 C. for 24 hours. Samples of the reaction mixture were taken and examined by HPLC. A yield of 19.6% 4,4′-bis(N-methylphthalimide)sulfide was indicated. The isolated yield was 18% (0.08 g).

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, 2-Methyl-5-nitroisoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; General Electric Company; US4625037; (1986); A;,
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 552330-86-6 as follows. COA of Formula: C8H6BrNO

General procedure: 5-Bromo-2-methylisoindolin-1-one (520 mg, 2.30 mmol) and thiophene-2-boronic acid (442mg, 3.45 mmol) were dissolved in a mixure of toluene (12 mL) and EtOH (6 mL). A solutionof 2 M Na2CO3 (3 mL) and Pd(dppf)Cl2 (94 mg, 0.12 mmol) were added and the entiremixture heated at reflux under N2 for 2 h. Additional thiophene-2-boronic acid (294 mg, 2.30mmol) was added and reflux continued under N2 overnight. Upon cooling, the mixture wasdiluted with water (100 mL) and extracted with CH2Cl2 (6×50 mL). The combined organicfractions were dried (Na2SO4), filtered, and the solvent removed under reduced pressure togive a crude solid which was purified by flash column chromatography on silica gel (EtOAcas eluant). The title compound was isolated as a light-brown solid (510 mg, 97%).

According to the analysis of related databases, 552330-86-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Spicer, Julie A.; Miller, Christian K.; O’Connor, Patrick D.; Jose, Jiney; Huttunen, Kristiina M.; Jaiswal, Jagdish K.; Denny, William A.; Akhlaghi, Hedieh; Browne, Kylie A.; Trapani, Joseph A.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 4; (2017); p. 1050 – 1054;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 2058-74-4, 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 2058-74-4 as follows.

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.

According to the analysis of related databases, 2058-74-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Chouhan, Mangilal; Senwar, Kishna Ram; Kumar, Kapil; Sharma, Ratnesh; Nair, Vipin A.; Synthesis; vol. 46; 2; (2014); p. 195 – 202;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 20876-36-2, These common heterocyclic compound, 20876-36-2, name is 5-Aminoindolin-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.

To a solution of 5-amino oxindole (2 g, 13.5 mmol) in 80 ml of water/dioxane 3:1 was added sodium hydroxide 1N until obtaining pH 10 and then di-t-Butyl pyrocarbonate (3.5 g, 16.2 mmol). The reaction was stirred for 3 h maintaining pH 10. After extraction with 3*10 ml of ethyl acetate, the extracted were dried over sodium sulphate and evaporated obtaining 2.4 g of 5-t-Butoxycarbonylamino oxindole (71percent yield). 1 H-NMR (400 MHz, DMSO, T=45¡ã C.) 1.49 (s, 9H); 3.87 (s, 3H); 6.72 (d, J=8.4 Hz, 1H); 6.86 (dd, J=2.2 Hz, J=8.8 Hz, 1H); 7.12 (dd, J=1.8 Hz, J=8.4 Hz, 1H); 7.40 (d, J=8.8 Hz, 1H); 7.54 (d, J=2.2 Hz, 1H); 7.78 (d, J=1.8 Hz, 1H); 7.92 (s, 1H); 8.87 (bs, 1H); 9.38 (s, 1H); 10.25 (s, 1H); 11.8 (bs, 1H). FD-MS: 248 (100, [M]+); 191 (18, M-C4 H9!+); 147 (5, M-(CH3)3[COCO]+)

The synthetic route of 20876-36-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pharmacia & Upjohn S.p.A.; US5849710; (1998); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 3339-73-9,Some common heterocyclic compound, 3339-73-9, name is 3-(1,3-Dioxoisoindolin-2-yl)propanoic acid, molecular formula is C11H9NO4, 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 4 (0.3 g, 1.37 mmol) in CH2Cl2 (10 mL) was added thionyl chloride (0.12 mL, 1.6 mmol). The resulting mixture was stirred at reflux for 5 h. After cooling to rt, the solvent and excess thionyl chloride were removed by evaporation to give a white solid (0.22 g) in 67% yield; 1H NMR (400 MHz, CDCl3) delta 7.87 (m, 2H), 7.74 (m, 2H), 4.04 (m, 2H), 3.35 (m, 2H); 13C NMR (100 MHz, CDCl3) delta 168.0, 166.2, 134.2, 123.5, 33.9, 33.0; mp 148-150?C. The product was used in the next step without further purification.

The synthetic route of 3339-73-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Peng; Jorgensen, Trine Nygaard; Loland, Claus J.; Newman, Amy Hauck; Bioorganic and Medicinal Chemistry Letters; vol. 23; 1; (2013); p. 323 – 326;,
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. 181140-34-1, name is (R)-(-)-N-(2,3-Epoxypropyl)phthalimide, A new synthetic method of this compound is introduced below., Formula: C11H9NO3

A mixture of 2,3-dihydro-1H-inden-2-amine (5.0 g, 24.61 mmol) and (R)-2-(oxiran-2-ylmethyl)isoindoline-1,3-dione (4.91 g, 36.91 mmol) in EtOH (100 mL) was heated at reflux overnight. After cooling to room temperature, triethylamine (9.94 g, 98.44 mmol) and (Boc)2O(10.74 g, 49.22 mmol) were added and the reaction mixture was stirred at room temperature overnight. The mixture was concentrated and purified by column (EtOAc / petroleum ether = 1/4, v/v) to give the title compound (5.4 g, 50%) as an oil.

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; CTxT PTY LIMITED; STUPPLE, Paul Anthony; (66 pag.)WO2017/153521; (2017); A1;,
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. 1914-02-9, name is 3,3-Dimethylindoline, A new synthetic method of this compound is introduced below., category: indolines-derivatives

A mixture of 3,3-dimethylindoline (2.1 g, 14.26 mmol) and 2-bromoethanamine hydrobromide (3.215 g,15.69 mmol) was heated at 122 C for 15 h. The mixture was dissolved in 2M HCl and purified bypreparative HPLC to give the title compound (1.9 g). LCMS m/z = 191.4 [M+H]+; 1H NMR (400 MHz,CD3OD) delta ppm 1.31 (s, 6H), 3.14 (s, 2H), 3.19 (t, 2H, J = 6.1Hz), 3.33 (t, 2H, J = 6.1 Hz), 6.60 (d, 1H, J = 7.9Hz), 6.70-6.76 (m, 1H), 7.01-7.09 (m, 2H).

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; Dang, Huong; Feichtinger, Konrad; Frazer, John; Grottick, Andrew J.; Kasem, Michelle; Le, Minh; Lehman, Juerg; Morgan, Michael E.; Ren, Albert; Sage, Carleton R.; Schrader, Thomas O.; Semple, Graeme; Unett, David J.; Whelan, Kevin T.; Wong, Amy; Zhu, Xiuwen; Bioorganic and medicinal chemistry letters; (2020);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem