Month: March 2021

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. 496-12-8, name is Isoindoline, A new synthetic method of this compound is introduced below., Application In Synthesis of Isoindoline

Part B. To a solution of the isoindoline (5.40 g, 21.3 mmol) made above in EtOH (266 mL) under N2 was added 20% Pd(OH)2/C (3.00 g, 4.25 mmol). The reaction mixture was hydrogenated at 45 psi for 1 h. TLC analysis indicated that the nitro functionality was reduced and the Bn group was still intact. Therefore, concentrated HCl (1.6 mL, 19.1 mmol) was added to the reaction mixture and hydrogenation (50 psi) was continued overnight. The mixture was filtered through Celite, washed with MeOH, and the filtrate was concentrated to one fourth of the volume. The precipitate was filtered off to provide the 5-aminoisoindoline.HCl (1.32 g, 36% yield): 1H NMR (500 MHz, CDCl3) delta9.88 (s, br, 2H), 7.00 (d, 1H), 6.54 (m, 2H), 5.44 (s, br, 2H), 4.32 (s, 2H), 4.28 (s, 2H); ESI MS m/z 135 (M-HCl+H)+.

The synthetic route of 496-12-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pinto, Donald J.P.; Quan, Mimi L.; Orwat, Michael J.; Li, Yun-Long; Han, Wei; Qiao, Jennifer X.; Lam, Patrick Y.S.; Koch, Stephanie L.; US2003/191115; (2003); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 446292-08-6, The chemical industry reduces the impact on the environment during synthesis 446292-08-6, name is (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione, I believe this compound will play a more active role in future production and life.

Into a 100ml three-neck round bottom flask was added the compound (III) (3.0g, 7.1mmol), 25% aqueous methylamine solution (3.89 g of the) and ethanol (22.5ml), heated to 60 ~ 70 for 2 to 3 hours, cooling to room temperature, concentrated hydrochloric acid was added to adjust PH 1-2, filtered, Suntory rivaroxaban V intermediate compound hydrochloride salt 1.98g, yield 85%

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, (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Changzhou Nan Fang Pharmaceutical Co., Ltd.; Zhang, Xini; Zi, Chunpeng; Wang, Yingqi; (7 pag.)CN105777734; (2016); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

611-09-6, name is 5-Nitroindoline-2,3-dione, 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. SDS of cas: 611-09-6

General procedure: To a solution of isatins 4a-h (1 mmol) and TiO2 NPs (8 mg, 0.1 mmol, 10 mol%) in water (3 mL), indoles 5a-d (2 mmol) were added and stirred for the indicated time(Table 2) at room temperature. The progress of the reaction was monitored by TLC, however, the same can be inferred by visualizing the disappearance of isatin color and white solid formation. After the consumption of starting material, as indicated by theTLC, the reaction mixture was filtered and the white solid was dried. The obtained solid was then dissolved in ethyl acetate (5 mL) and centrifuged for 1 h at 15000 rpm to separate nanoparticles. Later organic layer was passed through celite pad to remove any particulate impurities from the product and concentrated under reduced pressure. The product was further purified by recrystallization using methanol to give analytically pure 3,3-di(indolyl)indolin-2-ones 6a-r as solid.

The synthetic route of 611-09-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Dwivedi, Kartikey Dhar; Marri, Sameer Reddy; Nandigama, Satish Kumar; Chowhan, L. Raju; Synthetic Communications; vol. 48; 20; (2018); p. 2695 – 2707;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 611-09-6,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.

General procedure: The suspension of isatin 1a-c in hydrazine hydrate was refluxed for 5h until clear solution formation. After reaction completion the mixture was cooled down to room temperature and poured into cold water. Then pH value of the mixture was adjusted to 1-2 via concentrated hydrochloride acid addition. The reaction mixture was left at room temperature for 2-3days, the precipitate formed was filtered, washed with water and dried on air and was used without additional purification. The following compounds were obtained according to this general procedure:

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Nitroindoline-2,3-dione, its application will become more common.

Reference:
Article; Lozinskaya, Natalia A.; Babkov, Denis A.; Zaryanova, Ekaterina V.; Bezsonova, Elena N.; Efremov, Alexander M.; Tsymlyakov, Michael D.; Anikina, Lada V.; Zakharyascheva, Olga Yu.; Borisov, Alexander V.; Perfilova, Valentina N.; Tyurenkov, Ivan N.; Proskurnina, Marina V.; Spasov, Alexander A.; Bioorganic and Medicinal Chemistry; vol. 27; 9; (2019); p. 1804 – 1817;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 18711-13-2, 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. 18711-13-2 name is 4,7-Dichloroindoline-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.

General procedure: A mixture of isatin (1a) (0.3 gm, 2.0 mmol) and enaminone (2a) (0.333 gm,2.4 mmol) in 10 mL of water was heated in an oil bath at 80C for 9 hours. Initially,orange-colored reaction mixture appeared to be homogeneous but with the progress ofthe reaction, yellow color solid precipitated out. After the TLC indicated the completeconsumption of starting materials, the precipitated solid was filtered off. The solid wasthen dried under vacuum and purified by silica gel column chromatography by using EA: hexane (8:2) as an eluent to provide the desired product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4,7-Dichloroindoline-2,3-dione, and friends who are interested can also refer to it.

Reference:
Article; Tiwari, Keshri Nath; Thakar, Snehal Rajendra; Kumar, Vaneet; Prabhakaran; Synthetic Communications; vol. 48; 23; (2018); p. 2965 – 2972;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 667463-64-1, These common heterocyclic compound, 667463-64-1, name is 6-Bromo-1-methylindoline-2,3-dione, 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 6-bromorsatin (CASNo. 6326-79-0, 4 52 g, 20 0 mmol) in acetonrtrile (150 mL) was added potassium carbonate (11 1 g, 80 mmol) followed by iodomethane (2 75 mL, 44 0 mmol) The reactron was then placed at 60 C and stirred for 40 minutes The reaction was then cooled to room temperature, tittered and concentrated to 10% of the original volume The reaction was then diluted with dichloromethane, water and brine The layers were separated and the aqueous layer was extracted two additional times with dichloromethane. The organic extracts were combined, dried over anhydrous sodium sulfate filtered and concentrated to provide 6-bromo-1-methyl-1 H-iotandole-2,3- dione as an orange solid without the need for further punfication The beta-bromo-1-methyl- 1 H-iotandole-2,3-diotaone (1 0 g, 4 2 mmol) was then treated with hydrazine hydrate (7 0 mL, 225 mmol) The reaction was heated to 130 C and stirred for 80 minutes, at which time the reaction was placed at room temperature and cooled by the addition of ice Once the reaction was cooled to room temperature it was diluted with dichloromethane and water and the layers were separated The aqueous layer was extracted an additional two times with dichloromethane, and the organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated The resulting residue was purified by silica gel flash chromatography (ethanol-dichloromethane 0 to 2%) to afford 6-bromo- 1-methyl-1 ,3-diotahydro-mdol-2-one, MS (ES+) m/z 225 9 (IvH-H)*

Statistics shows that 6-Bromo-1-methylindoline-2,3-dione is playing an increasingly important role. we look forward to future research findings about 667463-64-1.

Reference:
Patent; NOVARTIS AG; ADAMS, Christopher Michael; CHAMOIN, Sylvie; HU, Qi-Ying; ZHANG, Chun; WO2010/130794; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 3485-84-5, 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. 3485-84-5 name is N-Vinylphthalimide, 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.

To a degassed solution of 3-bromo-5-(trifluoromethyl)aniline (1.00 g, 4.17 mmol) and ACN (40 mL) was added Pd(OAc)2 (0.46 g, 0.20 mmol), bis(2-methylphenyl)(3-methylphenyl)phosphine (0.13 g, 0.40 mmol), and TEA (1.15 mL, 8.25 mmol). After stirring for 1 h, 2-vinyl-1H-isoindole-1,3(2H)-dione (0.72 g, 4.17 mmol) was added. The solution was heated at reflux for 20 h and then allowed to cool to rt and filtered through Celite. The filtrate was washed with water and brine. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to yield the title compound as a yellow solid (0.90 g, 62%). LCMS: (FA) ES+ 333.2 (M+1).

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

Reference:
Patent; Millennium Pharmaceuticals, Inc.; US2006/160803; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 99365-40-9, A common heterocyclic compound, 99365-40-9, name is 6-Bromoindolin-2-one, molecular formula is C8H6BrNO, 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.

6-bromoindolin-2-one (25.2 mg, 0.119 mmol), N-(6-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)naphthalen-2-yl)thiophene-3-carboxamide (72.1 mg, 0.190 mmol), Fibercat palladium catalyst (Johnson-Matthey, 35.4 mg), and K2CO3 (2 M in water, 0.25 ml, 0.5 mmol) were combined in a microwave reaction vessel and 1 ,4-dioxane (1.1 ml) was added. The reaction tube was sealed and heated in the microwave (CEM microwave) at 60 Watts and 80 C, first for 10 minutes, and then for 20 minutes. The reaction was cooled to room temperature, diluted with water (5 ml), and extracted with dichloromethane (3 x 10 ml) and EtOAc (6 x 10 ml). The organic extracts were combined, dried over sodium sulfate, filtered, concentrated, and purified on HPLC (10% -> 95% MeCN / water with 0.1% EPO L <.) to arroralpha tiue compounalpha (7.1 mg, 16%). MS (ESI pos. ion) m/z: 385 (M+H). Calc'd Exact Mass for C23H16N2O2S: 384. The synthetic route of 99365-40-9 has been constantly updated, and we look forward to future research findings. Reference:
Patent; AMGEN INC.; WO2007/5668; (2007); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 2307-00-8, The chemical industry reduces the impact on the environment during synthesis 2307-00-8, name is 5-Amino-2-methylisoindoline-1,3-dione, I believe this compound will play a more active role in future production and life.

Example 110 2-METHYL-5-[(2-OXO-1-PHENYL-1,2-DIHYDRO-3H-INDOL-3-YLIDENE)AMINO]-2H-ISOINDOLE-1,3(2H)-DIONE: A mixture of 1-phenylisatin (50 mg, 0.22 mmol) and 4-amino-N-methylpthalimide (40 mg, 0.22 mmol) was heated neat at 215 C. for 2 h. The crude material was purified by preparative TLC using a mixture of 3:7 ethyl acetate and hexane as the eluent, giving the desired product as a yellow solid (8 mg, 0.02 mmol, 10%). 1H NMR (400 MHz): delta 7.88 (d, J=7.8, 1H), 7.83-7.80 (m, 1H), 7.51 (t, J=7.5, 1H), 7.47-7.18 (m, 6H), 7.02 (t, J=8.0, 1H), 6.91-6.79 (m, 2H), 6.58 (d, J=7.5, 1H), 3.22 (s, 3H); ESI-MS m/z found 382 (MH+).

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-Amino-2-methylisoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Konkel, Michael J.; Blackburn, Thomas P.; Wetzel, John M.; US2004/110821; (2004); 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. 480-91-1, name is Isoindolin-1-one, This compound has unique chemical properties. The synthetic route is as follows., Safety of Isoindolin-1-one

To a solution of isoindolin-1-one (120 mg 0.90 mmol) in MeCN (10 mL) was added Cs2CO3 (652 mg, 2.0 mmol) and ethyl 2-iodo-4-methylpentanoate (540 mg, 2.0 mmol). The mixture was stirred at 85 C. for 12 hours and filtered. The filtrate was concentrated under pressure, and the residue was purified by silica gel column (petroleum ether_EtOAc=3:1) to give the desired product ethyl 4-methyl-2-(1-oxoisoindolin-2-yl)pentanoate as a colorless oil (120 mg). Yield 50% (95% purity, UV=254 nm, ESI 276.1 (M+H)+).

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 480-91-1.

Reference:
Patent; Morphic Therapeutic, Inc.; Bursavich, Matthew G.; Troast, Dawn M.; Harrison, Bryce A.; Lippa, Blaise S.; Rogers, Bruce N.; Konze, Kyle D.; Gerasyuto, Aleksey I.; Day, Tyler; Lin, Fu-Yang; Hahn, Kristopher N.; Svensson, Mats A.; Kim, Byungchan; Zhong, Cheng; Lugovskoy, Alexey A.; Sosa, Brian; (263 pag.)US2019/315692; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem