Author: tianli

Adding some certain compound to certain chemical reactions, such as: 14192-26-8, name is Methyl 2-oxoindoline-6-carboxylate, 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 14192-26-8. 14192-26-8

2-oxo-2,3-dihydro-1H-indole-6-carboxylic acid methyl ester (3.17 g, 16.6 mmol) and orthobenzoic acid triethyl ester (11.1 g, 49.8 mmol) was suspended in acetic anhydride (15 mL) and toluene (15 mL). the mixture was stirred at 110 C. overnight. After that time, the solvent was removed by evaporation. The residue was triturated with 10 ml petroleum ether, filtered off, and dried at 50 C. under vacuum to give 6 g product. LCMS: m/z=366 (MH)+

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 Methyl 2-oxoindoline-6-carboxylate.

Reference:
Patent; Auspex Pharmaceuticals, Inc.; Rao, Tadimeti; Zhang, Chengzhi; US2015/284327; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

A common compound: 1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide, belongs to indolines-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 1074-82-4

8.7ml (6 ¡¤ 5 X 102 moles) 1,5-dibromopentane with6 g (3. 2 X 10 2 moles) Phthalimide potassium salt dissolved in 100ml of N, N- dimethylformamide andunder room temperatureit was stirred for 15hours.The solvent was distilled off under reduced pressure, The residue usingn-hexane: ethyl acetate with a volumeratio of 10: 1 eluent to carry out column chromatography, gradually increasingthe polarity to hexane: ethyl acetate with a volume ratio of 5: 1 to give a product of 6.9g(2.3X102 mol) a bromogroup substituted by Phthalimide. The product with 5. 9g (4. 7X 102 mol) of sodium sulfite, 140ml water and 85ml95% ethanol mixed reactionwas heated to 95 C for18h, the remainingsolvent was drained, and the resulting residue was mixed with 73ml ofconcentrated hydrochloric acidthen was heated to 110 C thefor 18H, it was drained, with water – 95% ethanol on the residue to carry out recrystallization to give 5-amino-1-pentylSulfonic acid 2. 7g (total yield 50%).

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, 1074-82-4, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Institute of Chemistry Chinese Academy of Sciences; zhao, jingquan; DENG, HONG; XEI, JIE; (16 pag.)CN101948412; (2016); B;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 15362-40-0, name is 1-(2,6-Dichlorophenyl)-2-indolinone, molecular formula is C14H9Cl2NO, 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. 15362-40-0

A finely ground mixture of chromone-3-carboxaldehyde(1 mmol) and oxindole/indolinone (1-(2,6-dichlorophenyl)-2-indolinone)/1-(3-chlorophenyl)-3-methyl-2-pyrazolin-5-one (1.2 mmol) was irradiated in microwave oven for 1 min and completion of the reaction was monitored with TLC. Reaction mixture was washed with diethyl ether to get pure compounds 5-10.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 15362-40-0, its application will become more common.

Reference:
Article; Shaveta; Singh, Amrinder; Kaur, Matinder; Sharma, Surbhi; Bhatti, Rajbir; Singh, Palwinder; European Journal of Medicinal Chemistry; vol. 77; (2014); p. 185 – 192;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

A common heterocyclic compound, 324-03-8, name is 6-Fluoroindoline-2,3-dione, molecular formula is C8H4FNO2, 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. 324-03-8.

General procedure: The typical process for preparation of isatin-DHEAconjugates 4a-e is shown as following: To a solution of dehydroepiandrosterone-17hydrazone 3 (0.3 g, 1 mmol) inethanol (15 mL) was added the equal amounts of substituted isatin (1 mmol), which werestirred at ambient temperature or 50 oC and detected by thin-layerchromatography. Then the solution was concentrated, and the condensation product 4a-eseparated out on cooling (0-4 oC) and was recrystallized from ethanol. All the compounds were characterized by ESI-MS, 1HNMR spectroscopic data

The synthetic route of 6-Fluoroindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ke, Shaoyong; Shi, Liqiao; Yang, Ziwen; Bioorganic and Medicinal Chemistry Letters; vol. 25; 20; (2015); p. 4628 – 4631;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

2058-72-2, A common compound: 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, belongs to indolines-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

General procedure: A two-necked round-bottom flask with a magnetic stirring bar was flushed with nitrogen at r.t. MgBr2 (225 mg, 1.2 mmol), an N-substituted isatin 1 (1.0 mmol), ethyl propiolate (2; 1.3 equiv) and freshly distilled CH2Cl2 (5.0 mL) were added to the flask. The suspension mixture was stirred at r.t. for 5 h before turning into a pale yellow, homogeneous solution. The reaction was quenched by the dropwise addition of 10 % aqueous NaHCO3 (3 mL). The resulting two phases were separated, and the aqueous phase was extracted with EtOAc (30 mL). The combined organic layer was then washed with brine, dried over anhydrous MgSO4 and concentrated. The obtained crude product was purified by silica gel column chromatography (EtOAc/hexane, 20:80) to afford the corresponding ester 3.

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

Reference:
Article; Lingam, Kandapalam Arun Prasath; Amutha, Periyasamy; Yuvaraj, Paneerselvam; Selvakumar, Kodirajan; Synthesis; vol. 50; 3; (2018); p. 599 – 606;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

222036-66-0, 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. 222036-66-0, name is 5-Aminoisoindolin-1-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Step 4: 5-f(2-mS,2SV2-ri-(5-chloropyrimidin-2-vnpiperidin-4- yllcyclorhororhoyl}efoyl)amino1isoindolin- 1 -one2-{(lS,2R)-2-[l-(5-chloropyrimidin-2-yl)piperidin-4-yl]cycIopropyl}ethyl 4- methylbenzenesulfonate from step 1 of Example 5 (100 mg, 0.23 mmol) was dissolved in sulfolane and 5-aminoisoindolin-1-one (68 mg, 0.46 mmol) from step 3 of this example added. The mixture was at stirred 110 ¡ãC for 3 and at 120 ¡ãC for 2 hours.The mixture was cooled to RT, diluted with 4:1 water: saturated sodium bicarbonate (40 ml), extracted with EtOAc (3×30 ml), the organic fractions combined, washed with brine, dried over Na2SO4, filtered, the volatiles removed in vacuum. The product was purified by chromatography on SiO2 eluting with 80percent acetone : hexanes to give the titled compound. LRMS calc: 411.18; obs: 412.08 (M+l).

The synthetic route of 5-Aminoisoindolin-1-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WOOD, Harold, B.; ADAMS, Alan, D.; SZEWCZYK, Jason, W.; ZHANG, Yong; YANG, Meng; WO2011/19538; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 3416-57-7, name is 2-(2-Oxopropyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. 3416-57-7

To a refluxed mixture of 4.63 M sodium methoxide in methanol (55.0 mL, 254 mmol) and methanol (500 mL) was added solid N-acethonylphthalimide (25.00 g, 123.0 mmol, from TCI) in one portion. After addition, the reaction was heated at reflux for 2 hours, then cooled at 0 C and neutralized with 1 N HCl. The resulting suspension was stirred at 0 C for 30 minutes and then filtered under reduced pressure, washed with a small amount of water and air dried. The resulting solid was further dried under vacuum, over P2O5, to give the desired product (21.2 g, 85%). LCMS calculated for CnHi0NO3 (M+H)+: m/z = 204.1; Found: 204.0.

The synthetic route of 3416-57-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INCYTE CORPORATION; LI, Yun-Long; COMBS, Andrew, P.; YUE, Eddy, W.; LI, Hui-Yin; WO2011/75630; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

A common heterocyclic compound, 603-62-3, name is 3-Nitrophthalimide, molecular formula is C8H4N2O4, 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. 603-62-3.

Compound 25-2: A mixture of 4-nitroisoindoline-1,3-dione (25 g, 130.1 mmol), NaBH4 (11.13 g, 294.0 mmol) in MeOH (250 mL) was degassed and purged with N2 3 times. The mixture was stirred at 25 C. for 2 h under an N2 atmosphere. The solution was acidified with 20% HCl (100 mL) and the reaction mixture was concentrated under reduced pressure to give a residue. The dried residue was treated with acetone. The residue was purified by column chromatography (SiO2, petroleum ether:ethyl acetate=10:1 to 0:1). Compound 25-2, 3-hydroxy-4-nitroisoindolin-1-one (15 g, 59% yield) was obtained as a yellow solid.

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

Reference:
Patent; Cervello Therapeutics LLC; Lee, Matthew Randolph; Varano, JR., Anthony Joseph; (53 pag.)US2020/140412; (2020); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 99365-40-9 name is 6-Bromoindolin-2-one, 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. 99365-40-9

(293-1) 3,3-Dimethyl-6-bromoindolin-2-one A solution (50 ml) of 6-bromoindolin-2-one (3.18 g) in THF was cooled to -78 C. and 1.5 M lithium diisopropylamide (20 ml) was added dropwise thereinto followed by stirring for 15 min. After adding methyl iodide (0.92 ml), the reaction mixture was brought to room temperature and stirred for 1 hr. Then the reaction solution was cooled to -78 C. again and 1.5 M lithium diisopropylamide (10 ml) was added dropwise thereinto followed by stirring for 15 min. After adding methyl iodide (0.92 ml), the reaction solution was brought to room temperature with stirring. Then a saturated aqueous solution of ammonium chloride was added thereto and the resultant mixture was extracted with ethyl acetate. The residue was washed with hexane to give the title compound (3.35 g) as a white amorphous solid (yield: 93.0%). 1H-NMR (400 MHz, CDCl3): delta(ppm) 1.38(6H, s), 7.05(1H, d, J=8.0Hz), 7.096(1H, d, J=1.6Hz), 7.169(1H, d, J=1.6Hz), 8.41(1H, m).

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

Reference:
Patent; Eisai Co., Ltd.; US2002/19531; (2002); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

3416-57-7,Some common heterocyclic compound, 3416-57-7, name is 2-(2-Oxopropyl)isoindoline-1,3-dione, molecular formula is C11H9NO3, 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 1: (E&Z)-2-(4-(Dimethylamino)-2-oxobut-3-en-1-yl)isoindoline-1,3-dione A mixture of 2-(2-oxopropyl)isoindoline-1,3-dione (2.03 g, 10 mmol) and 1,1-dimethoxy-N,N-dimethyl-methanamine (1.3 ml, 10 mmol) was irradiated by microwave at 180 C. for 20 minutes. The resulting solid was recrystallized from ethanol to provide the title product as a mixture of cis- & trans-isomers 2.34 g (91% yield). ESMS(M+1)=259.10.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(2-Oxopropyl)isoindoline-1,3-dione, its application will become more common.

Reference:
Patent; Vertex Pharmaceuticals Incorporated; Lauffer, David J.; Bemis, Guy; Boyd, Michael; Deininger, David; Deng, Hongbo; Dorsch, Warren; Gu, Wenxin; Hoover, Russell R.; Johnson, JR., Mac Arthur; Ledeboer, Mark Willem; Ledford, Brian; Maltais, Francois; Penney, Marina; Takemoto, Darin; Waal, Nathan D.; Weng, Tiansheng; (667 pag.)US2019/322673; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem