Category: 19155-24-9

Application of 19155-24-9, A common heterocyclic compound, 19155-24-9, name is 3,3-Dimethylindolin-2-one, 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.

3,3-dimethyl-indol-2-one (0.65 g, 4.03 mmol) and sodium acetate (0.33 g, 4.07 mmol) were stirred in acetic acid (5 cm3) then bromine (0.66 g, 4.13 mmol) in acetic acid (5 cm3) was added drop-wise to the reaction mixture. The reaction was stirred for 50 min., then poured into water. The mixture was basified with sodium carbonate, extracted with ethyl acetate (.x.3), dried (MgSO4), filtered, and evaporated to give the subtitled compound (0.89 g, 92percent) 1H NMR (DMSO-d6) delta 1.21 (s, 6 H), 6.76 (d, 1 H, J=8.22 Hz), 7.29 (dd, 1 H, J=2.12 Hz, 8.23 Hz), 7.49 (d, 1 H, J=2.03 Hz), 10.4 (s, 1H).

The synthetic route of 19155-24-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; American Home Products Corporation; Ligand Pharmaceuticals, Inc.; US6355648; (2002); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 19155-24-9, 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. 19155-24-9, name is 3,3-Dimethylindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 3,3-dimethylindolin-2-one (31) (12.9 mg, 0.08 mmol), 4-bromo-2-methoxybenzonitrile (30) (17.0 mg, 0.08 mmol), COPPER (I) IODIDE (7.80 mg, 0.04 mmol), TRANS- (1R, 2R)- N, N’- DIMETHYL- CYCLOHEXANE- 1, 2- DIAMINE (11.7 mg, 0.08 mmol) and POTASSIUM PHOSPHATE (35.0 mg, 0.16 mmol) in DMSO (0.50 mL) was heated to 80C for 1.5 h, then heated to 100C for 21h. The reaction mixture was diluted with ethyl acetate, filtered through a plug of silica gel and concentrated by rotary evaporation. The resulting residue was purified by prep-HPLC to afford 4-(3,3-dimethyl-2-oxoindolin-1-yl)-2-methoxybenzonitrile (32) (8.75 mg, 37percent). 1H NMR (500 MHz, DMSO-d6) d ppm 1.41 (s, 6 H) 3.95 (s, 3 H) 6.95 (d, J=7.81 Hz, 1 H) 7.14 (t, J=7.32 Hz, 1 H) 7.20 (d, J=7.81 Hz, 1 H) 7.24 (t, J=7.81 Hz, 1 H) 7.36 (s, 1 H) 7.46 (d, J=6.83 Hz, 1 H) 7.90 (d, J=7.81 Hz, 1 H)

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

Reference:
Article; Guo, Chuangxing; Pairish, Mason; Linton, Angelica; Kephart, Susan; Ornelas, Martha; Nagata, Asako; Burke, Benjamin; Dong, Liming; Engebretsen, Jon; Fanjul, Andrea N.; Bioorganic and Medicinal Chemistry Letters; vol. 22; 7; (2012); p. 2572 – 2578;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 19155-24-9, 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 19155-24-9 as follows.

Preparation of l-(3-chloropropyl)-3,3-dimethylindolin-2-one; [0231] A solution of 3,3-dimethylindolin-2-one (1.843 g, 11.43 mmol, 1 equiv) in N,N- dimethylformamide was cooled to 0¡ãC. Sodium hydride (60percent dispersion) (503 mg, 12.58 mmol, 1.1 equiv) was slowly added and the reaction was stirred as such until all bubbling had stopped. 1 – bromo-3-chloropropane (3.37 ml, 34.3 mmol, 3 equiv) was added to the reaction mixture in one portion. The reaction was allowed to warm to ambient temperature and stirred as such for 16 h. The crude mixture was partitioned between ethyl acetate and water. The organic layer was dried over MgSO i, filtered, concentrated, and the residue was purified using the Biotage flash chromatography system (SNAP 50 g cartridge, R/= 0.5, gradient – 5percent>-30percent> ethyl acetate in hexanes) to afford the title compound as a light orange oil (2.38 g, 87percent); ‘i/NMR (400 MHz, DMSO-i/6): delta 1.26 (s, 6H); 1.98-2.14 (m, 2H); 3.65 (t, 2H, J= 6 and 6.8 Hz); 3.77-3.81 (m, 2H); 7.02-7.07 (m, 2H); 7.24-7.28 (m, 1H); 7.33-7.35 (m, 1H); MS for C13H16C1N0 m/z 237.99 (M+H)+.

According to the analysis of related databases, 19155-24-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALTOS THERAPEUTICS, LLC; LUEHR, Gary, W.; SUNDARAM, Arathi; JAISHANKAR, Priyadarshini; PAYNE, Philip, W.; DRUZGALA, Pascal; WO2011/160084; (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. 19155-24-9, name is 3,3-Dimethylindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 3,3-Dimethylindolin-2-one

3,3-dimethyl-2,3-dihydro-1H-indol-2-one (500 mg, 3.10 mmol) was dissolved in dry CH2CI2 (25 mL). Tetrabutylammonium tribromide (3.74 g, 7.75 mmol) was added portion wise to the solution. The reaction mixture was stirred at rt overnight. Water was added to quench the reaction. After phases separation, the organic layer was dried over Mg504, filtered and the solutionwas concentrated under reduced pressure. The crude material was purified by silica gel column chromatography eluting with Cyclohexane/EtOAc (70:30). Product fractions were collected and evaporated to dryness to afford 5-bromo- 3,3-dimethyl-2,3-dihydro-1 H-indol-2-one Ex.85a (730 mg, 3.04 mmol) as yellow solid. 1H NMR (300 MHz, DMSO-d6, din ppm): 1.24 (s, 6H), 6.79 (d, 1H, J=8.2Hz), 7.32 (dd, 1H, J=8.OHz, J=2.lHz), 7.52 (d, 1H, J=2.lHz), 10.44 (s, 1 H).

The synthetic route of 19155-24-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENFIT; DELHOMEL, Jean-Francois; PERSPICACE, Enrico; MAJD, Zouher; PARROCHE, Peggy; WALCZAK, Robert; (284 pag.)WO2018/138362; (2018); 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. 19155-24-9, name is 3,3-Dimethylindolin-2-one, A new synthetic method of this compound is introduced below., Quality Control of 3,3-Dimethylindolin-2-one

2c. 3,3-dimethylindoline:; To a 1M of LAH (30 mL) in THF was added 2b (630 mg, 3.88 mmol) in portion. The reaction mixture was stirred at rt for 2 h, then refluxed for 1 h. The reaction mixture was quench with 1 part of H2O (10-mL), one part of 15percent NaOH (5 mL) and another part of H2O (5 mL). The aqueous layer was extracted with EtOAc. The EtOAc layer was dried over Na2SO4 and filtered. The solvent was evaporated under reduced pressure to afford 2c (320 mg, 56percent) as an oil. MS (ES) m/z 150 [M+H]+.

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; Bristol-Myers Squibb Company; US2006/293281; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 19155-24-9, A common heterocyclic compound, 19155-24-9, name is 3,3-Dimethylindolin-2-one, 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.

Example 1; 5-amino-1-ethyl-3,3-dimethylindolin-2-one; Compound a (38.4 g), prepared according to the procedures described in Robertson et. al. (J. Med. Chem. 29(10) 1832-1840 (1986)), was dissolved in 300 ml of conc. sulfuric acid using mechanical stirring and cooled using a -40¡ã C. bath until the reaction became very thick. A solution of 10.1 ml of fuming nitric acid and 50 ml of conc. sulfuric acid was added dropwiseover 30 min. The reaction was allowed to warm to ambient temperature with stirring for 12 hours. The reaction mixture was poured into ice water and compound b was collected by filtration and dried (yield: 31 g).

The synthetic route of 19155-24-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Rawson, Thomas E.; Safina, Brian; Dotson, Jennafer; Zhou, Aihe; Aliagas-Martin, Ignacio; Halladay, Jason; Liang, Jun; Rueth, Matthias; Zhu, Bing-Yan; US2007/37791; (2007); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 19155-24-9, 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. 19155-24-9 name is 3,3-Dimethylindolin-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.

Example 1 5-amino-l-ethyl-3,3-dimethylindolin-2-one; Compound a (38.4 g), prepared according to the procedures described in Robertson et.al. (J. Med. Chem. 29(10) 1832-1840 (1986)), was dissolved in 300 ml of cone, sulfuric acid using mechanical stirring and cooled using a -40 C cooling bath until stirring became difficult. A solution of 10.1 ml of fuming nitric acid and 50 ml of cone, sulfuric acid was added dropwise and the reaction allowed to warm to ambient temperature with stirring for 12 hours. The reaction mixture was poured into ice water and compound b was collected by filtration and dried (yield: 3Ig).

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

Reference:
Patent; GENENTECH, INC.; WO2007/120339; (2007); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 19155-24-9, 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. 19155-24-9 name is 3,3-Dimethylindolin-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.

22c. 3,3-dimethylindoline To a solution of 22b (1.0 g, 6.2 mmol) in THF at 0¡ã C. was added LiAlH4 (1M THF solution, 13.6 mL, 2.2 eq) under nitrogen. The resulting slurry was heated at reflux for 4 h. While cooling in an ice bath, sat’d Na2SO4 was added carefully to quench the extra un-reacted LiAlH4. The solids were filtered out, and were rinsed with EtOAc. The organic was washed with H2O, brine, dried over MgSO4, filtered, and concentrated to dryness to give almost pure 22c (0.82 g, yield: 89percent). LC-MS ESI 148 (M+H).

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

Reference:
Patent; Tuerdi, Huji; Chao, Hannguang J.; Qiao, Jennifer X.; Wang, Tammy C.; Gungor, Timur; US2005/261244; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 19155-24-9, name is 3,3-Dimethylindolin-2-one, 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 19155-24-9, Computed Properties of C10H11NO

Step 4: 3,3-dimethyl-2,3-dihydro-1H-indole Under a nitrogen atmosphere a solution of 6.20 mL (6.20 mmol) of a 1M solution lithium aluminium hydride in THF and 10 mL THF was slowly added dropwise to 1.00 g (6.20 mmol) 3,3-dimethyl-1,3-dihydro-indol-2-one in 50 mL THF. Then the reaction mixture was heated to 60 C. for 1 h. After cooling to 0 C., 3 mL ice water were slowly added dropwise. 20 g sodium sulphate were added and the mixture was suction filtered. The solution was evaporated down i. vac. Yield: 0.80 g (88% of theory) ESI-MS: m/z=148 (M+H)+

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, 3,3-Dimethylindolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/195954; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 19155-24-9, name is 3,3-Dimethylindolin-2-one, molecular formula is C10H11NO, 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. Recommanded Product: 19155-24-9

A solution of 3,3-dimethylindolin-2-one (1.5 g, 9.31 mmol)Was dissolved in tetrahydrofuran (90 mL)The solution was cooled to 0 C,To this was added borane-tetrahydrofuran (37.3 mL, 37.22 mmol).The reaction solution was refluxed at 87 C overnight,Cooled to room temperature and quenched with methanol (10 mL).The mixture was further refluxed at 85 C for 2 hours, after which it was concentrated under reduced pressure.The residue was purified by silica gel column chromatography (petroleum ether / ethyl acetate (v / v) = 20/1)The title compound was obtained as a yellow oil (0.87 g, 63.5%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 19155-24-9, its application will become more common.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jiatuo Sciences Corporation; Xi Ning; Wang Ruyong; Wang Liang; (112 pag.)CN104016979; (2017); B;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem