959235-95-1 Archives - Indolines-derivatives

September 29, 2021 News Brief introduction of 959235-95-1

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. 959235-95-1, name is 6-(Trifluoromethoxy)indoline, This compound has unique chemical properties. The synthetic route is as follows., Formula: C9H8F3NO

Under N2 flow at 5C, propylphosphonic anhydride (2.56 ml_, 4.26 mmol) was added dropwise to a mixture of 6-(thfluoromethoxy)indoline [CAS 953906-76-8] (577 mg, 2.84 mmol), 2-(4-chlorophenyl)-2-((3-(2-hydroxyethoxy)-5-methoxy- phenyl)amino)acetic acid 3f (1 .3 g, 3.70 mmol) and diisopropylethylamine (1 .03 ml_, 6.25 mmol) in 2-Me-THF (30 ml_). The mixture was stirred at room temperature for 4 h. Water was added and the mixture was extracted with EtOAc. The organic layer was washed with a 10% solution of K2CO3 in water and then with water, dried over MgSO4, filtered, and the solvent was evaporated under reduced pressure. Purification was carried out by flash chromatography on silica gel, (15-40 muiotatauiota, 40 g, Ch C /MeOH 99/1 ). The pure fractions were combined and evaporated to dryness, to give 2-(4-chlorophenyl)-2-((3-(2-hydroxyethoxy)-5- methoxyphenyl)amino)-1 -(6-(trifluoromethoxy)indolin-1 -yl)ethanone (Compound 3, 800 mg) as a racemic mixture. This fraction was combined with another batch (total amount: 1 .4 g) and crystallized from diisopropyl ether to give 1 .03 g of Compound 3. The enantiomers were separated via Preparative Chiral SFC (Stationary phase: Chiralpak IA 5 muetaeta 250 x 20 mm, Mobile phase: 55% CO2, 45% EtOH (+ 0.3% iPrNh )). The first eluted enantiomer was further purified via reverse phase chromatography (stationary phase: X-bridge-C-18 10 m 30 x 150 mm, mobile phase: 0.2% NH4HCO3/CH3CN gradient 60/40 to 0/100) to give Enantiomer 3A (312 mg). The second eluted Enantiomer 3B (436 mg) was not further purified.

You can get involved in discussing the latest developments in this exciting area about 6-(Trifluoromethoxy)indoline.

Reference:
Patent; JANSSEN PHARMACEUTICALS, INC.; KATHOLIEKE UNIVERSITEIT LEUVEN; BARDIOT, Dorothee Alice Marie-Eve; BONFANTI, Jean-Francois; KESTELEYN, Bart Rudolf Romanie; MARCHAND, Arnaud Didier M; RABOISSON, Pierre Jean-Marie Bernard; (76 pag.)WO2017/167953; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

S News Extended knowledge of 959235-95-1

With the volume and accessibility of scientific research increasing across the world, it has never been more important to continue building the reputation for quality and ethical publishing we’ve spent the past two centuries establishing., category: indolines-derivatives

A mixture of 6-(trifluoromethoxy)indoline [CAS 959235-95-1 ] (837 mg, 4.12 mmol), 2-(2-(2-((fe/t-butyldimethylsilyl)oxy)ethoxy)-4-chlorophenyl)-2-((3-methoxy-5-(1 /-/- 1 ,2,4-triazol-1 -yl)phenyl)amino)acetic acid 5d (2.196 g, 4.12 mmol), HATU (2.35 g, 6.18 mmol) and diisopropylethylamine (2 ml_, 12.36 mmol) in DMF (20 ml_) was stirred at room temperature for 2 h. The mixture was diluted with water. The resulting gummy material was taken up with EtOAc, washed with a solution of K2CO3 10% in water, water, dried over MgSO4, filtered and the solvent was concentrated under reduced pressure. The residue was purified by flashchromatography on silica gel (15-40 muiotatauiota, 80 g, heptane/EtOAc gradient 70/30 to 60/40). The pure fractions were combined and the solvent was concentrated under reduced pressure to give 2-(2-(2-((terf-butyldimethylsilyl)oxy)ethoxy)-4- chlorophenyl)-2-((3-methoxy-5-(1 H-1 ,2,4-triazol-1 -yl)phenyl)amino)-1 -(6- (trifluoromethoxy)indolin-1 -yl)ethanone 6a (1 .65 g).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; JANSSEN PHARMACEUTICALS, INC.; KATHOLIEKE UNIVERSITEIT LEUVEN; KESTELEYN, Bart Rudolf Romanie; BONFANTI, Jean-Francois; COESEMANS, Erwin; RABOISSON, Pierre Jean-Marie Bernard; MARCHAND, Arnaud Didier M; BARDIOT, Dorothee Alice Marie-Eve; (92 pag.)WO2018/178240; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 959235-95-1

Electric Literature of 959235-95-1, These common heterocyclic compound, 959235-95-1, name is 6-(Trifluoromethoxy)indoline, 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 2-(2-(2-((fe/t-butyldimethylsilyl)oxy)ethoxy)-4-fluorophenyl)-2-((3- methoxy-5-(1 H-1 ,2,4-triazol-1 -yl)phenyl)amino)acetic acid 1f (1 .02 g, 1 .974 mmol) in DMF (10 ml_) were added HATU (1 .13 g, 2.96 mmol), diisopropylethylamine (979 muIota_, 5.92 mmol) and 6-(trifluoromethoxy)indoline [CAS 959235-95-1 ] (401 mg, 1 .97 mmol). The reaction mixture was stirred at room temperature for 2 h. The reaction mixture was diluted with water. The precipitate was filtered off, washed with water and taken up with EtOAc. The organic layer was washed with a 10% solution of K2CO3 in water, water, dried over MgSO4, filtered and the solvent was concentrated under reduced pressure to give 2-(2-(2-((terf-butyldimethylsilyl)- oxy)ethoxy)-4-fluorophenyl)-2-((3-methoxy-5-(1 H-1 ,2,4-triazol-1 -yl)phenyl)amino)- 1 -(6-(trifluoromethoxy)indolin-1 -yl)ethanone 3a (1 .34 g). The crude compound was used directly in the next reaction step.

The synthetic route of 959235-95-1 has been constantly updated, and we look forward to future research findings.

New learning discoveries about 959235-95-1

Adding a certain compound to certain chemical reactions, such as: 959235-95-1, name is 6-(Trifluoromethoxy)indoline, 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 959235-95-1, Quality Control of 6-(Trifluoromethoxy)indoline

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, 6-(Trifluoromethoxy)indoline, other downstream synthetic routes, hurry up and to see.

New downstream synthetic route of 959235-95-1

A mixture of 6-(trifluoromethoxy)indoline [CAS 959235-95-1] (2 g, 9.84 mmol), 2-(4-chlorophenyl)acetic acid [CAS 1878-66-6] (1 .85 g, 10.8 mmol), HATU (5.6 g, 14.8 mmol) and diisopropylethylamine (4.9 ml_, 29.5 mmol) in DMF (40 ml_) was stirred at room temperature for 12 h. Water was added and the precipitate was filtered off. The residue was taken up with EtOAc. The organic solution was washed with a 10% aqueous solution of K2CO3, brine, dried over MgSO4, filtered and the solvent was evaporated under reduced pressure. The residue was purified by chromatography on silica gel (15-40 muiotatauiota, 80 g, heptane/EtOAc gradient 90/10 to 60/40). The pure fractions were combined and the solvent was concentrated under reduced pressure to give 2-(4-chlorophenyl)-1 -(6-(trifluoromethoxy)indolin-1 -yl)- ethanone 4a (3 g).

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 959235-95-1.

Reference:
Patent; JANSSEN PHARMACEUTICALS, INC.; KATHOLIEKE UNIVERSITEIT LEUVEN; KESTELEYN, Bart Rudolf Romanie; RABOISSON, Pierre Jean-Marie Bernard; BONFANTI, Jean-Francois; BARDIOT, Dorothee Alice Marie-Eve; MARCHAND, Arnaud Didier M; (74 pag.)WO2017/167951; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

The important role of C9H8F3NO

Synthetic Route of 959235-95-1,Some common heterocyclic compound, 959235-95-1, name is 6-(Trifluoromethoxy)indoline, molecular formula is C9H8F3NO, 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.

A mixture of 6-(trifluoromethoxy)indoline [CAS 959235-95-1 ] (590 mg, 2.9 mmol), 2-(2-(4-(fe/t-butoxy)-4-oxobutoxy)-4-chlorophenyl)-2-((3-methoxy-5-(1 /-/-1 ,2,4- triazol-1 -yl)phenyl)amino)acetic acid 11d (1 .5 g, 2.9 mmol), HATU (1 .65 g, 4.35 mmol) and diisopropylethylannine (1 .45 mL, 8.7 mmol) in DMF (60 mL) was stirred at room temperature for 12 h. The mixture was diluted with water. The precipitate was filtered off, washed with water and taken up with EtOAc. The organic layer was washed with water, dried over MgSO4, filtered and the solvent wasconcentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (15-40 muiotatauiota, 120 g, heptane/EtOAc 60/40). The pure fractions were combined and concentrated to dryness to give, after crystallization from ether/diisopropyl ether, terf-butyl 4-(5-chloro-2-(1 -((3-methoxy-5-(1 H-1 ,2,4- triazol-1 -yl)phenyl)amino)-2-oxo-2-(6-(trifluoromethoxy)indolin-1 -yl)ethyl)phenoxy)- butanoate 13a (1 .05 g).

The synthetic route of 959235-95-1 has been constantly updated, and we look forward to future research findings.

Application of 959235-95-1

These common heterocyclic compound, 959235-95-1, name is 6-(Trifluoromethoxy)indoline, 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. Safety of 6-(Trifluoromethoxy)indoline

HATU (2.10 g, 5.52 mmol) was added to a mixture of 6-(trifluoromethoxy)indoline [CAS 953906-76-8] (747 mg, 3.68 mmol), 2-((3-(2-(terf-butoxy)ethoxy)-5-methoxy- phenyl)amino)-2-(4-chlorophenyl)acetic acid 3c (1 .5 g, 3.68 mmol) and diisopropylethylamine (1 .82 mL, 1 1 .03 mmol) in DMF (30 mL). The resulting mixture was stirred at room temperature for 12 h. The mixture was diluted with water and extracted with EtOAc. The organic layer was separated, dried over MgSO4, filtered and the solvent was evaporated under reduced pressure. Purification was carried out by flash chromatography on silica gel (15-40 muiotatauiota, 40 g, heptane/EtOAc 85/15). The pure fractions were combined and evaporated to dryness to give 2-((3-(2-(fe/t-butoxy)ethoxy)-5-methoxyphenyl)amino)-2-(4-chloro- phenyl)-1 -(6-(trifluoromethoxy)indolin-1 -yl)ethanone 3d (1 .33 g).

The synthetic route of 6-(Trifluoromethoxy)indoline has been constantly updated, and we look forward to future research findings.

Introduction of a new synthetic route about 959235-95-1

Electric Literature of 959235-95-1, 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. 959235-95-1 name is 6-(Trifluoromethoxy)indoline, 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.

A mixture of 6-(trifluoromethoxy)indoline [CAS 959235-95-1 ] (5 g, 24.6 mmol), 2-(4-chlorophenyl)acetic acid [CAS 1878-66-6] (4.2 g, 24.6 mmol), HATU (14.3 g, 36.9 mmol) and diisopropylethylamine (12.2 mL, 73.8 mmol) in DMF (60 mL) was stirred at room temperature for 20 h. The mixture was poured out slowly into stirring H2O (275 mL) and the resulting suspension was stirred for 50 minutes. The solids were filtered off and washed (4x) with H2O. The solid residue was taken up in toluene (125 mL), filtered over a paper filter, and the filtrate was evaporated under reduced pressure. The solid residue was stirred up in Et2O/heptane 2/1 (30 mL), filtered off, washed (3x) with Et2O/heptane 1/1 , and dried under vacuum at 50C to provide 2-(4-chlorophenyl)-1 -(6-(trifluoromethoxy)indolin-1 -yl)ethanone 1 b (7.33 g).

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

Reference:
Patent; JANSSEN PHARMACEUTICALS, INC.; KATHOLIEKE UNIVERSITEIT LEUVEN; BONFANTI, Jean-Francois; KESTELEYN, Bart, Rudolf, Romanie; BARDIOT, Dorothee, Alice, Marie-Eve; MARCHAND, Arnaud, Didier, M; COESEMANS, Erwin; FORTIN, Jerome, Michel, Claude; MERCEY, Guillaume, Jean, Maurice; RABOISSON, Pierre, Jean-Marie, Bernard; (153 pag.)WO2018/215315; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Extended knowledge of 959235-95-1

Application of 959235-95-1, The chemical industry reduces the impact on the environment during synthesis 959235-95-1, name is 6-(Trifluoromethoxy)indoline, I believe this compound will play a more active role in future production and life.

A mixture of 6-(trifluoromethoxy)indoline [CAS 959235-95-1] (577 mg, 2.84 mmol),2-(2-(4-(tert-butoxy)-4-oxobutoxy)-4-ch lorophenyl )-2-((3-methoxy-5-(methylsulfonyl)phenyl)amino)acetic acid 7d (1 .5 g, 2.84 mmol), HATU (1 .62 g, 4.26 mmol) and diisopropylethylamine (1 .4 mL, 8.5 mmol) in DMF (60 mL) was stirred at room temperature for 12 h. The mixture was diluted with water. The precipitate was filtered off and washed with water. The precipitate was taken upwith EtOAc, washed with an aqueous solution of K2003 10%, water, dried over MgSO4, filtered and the solvent was concentrated under reduced pressure. Purification was performed by flash chromatography on silica gel (15-40 pm, 120 g, heptane/EtOAc 60/40) to give, after crystallization from petroleum ether/diisopropyl ether, tert-butyl 4-(5-chloro-2-(1 -((3-methoxy-5-(methylsulfonyl)phenyl)amino)-2-oxo-2-(6-(trifluoromethoxy)indolin-1 -yl)ethyl)phenoxy)butanoate 9a (1 .02 g).

Reference:
Patent; JANSSEN PHARMACEUTICALS, INC.; KATHOLIEKE UNIVERSITEIT LEUVEN; BARDIOT, Dorothee Alice Marie-Eve; KESTELEYN, Bart Rudolf Romanie; BONFANTI, Jean-Francois; RABOISSON, Pierre Jean-Marie Bernard; MARCHAND, Arnaud Didier M; (64 pag.)WO2018/178238; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Extended knowledge of C9H8F3NO

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

Reference of 959235-95-1, 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. 959235-95-1 name is 6-(Trifluoromethoxy)indoline, 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 solution of 2-(2-(2-((tert-butyldimethylsilyl)oxy)ethoxy)-4-chlorophenyl)-2-((3-methoxy-5-(methylsulfonyl)phenyl)amino)acetic acid 5d (1 .07 g, 1 .97 mmol) inDMF (10 mL) were added HATU (1 .12 g, 2.95 mmol), diisopropylethylamine (976 pL, 5.91 mmol) and 6-(trifluoromethoxy)indoline [CAS 959235-95-1] (400 mg, 1 .97 mmol). The reaction mixture was stirred at room temperature for 2 h. The reaction mixture was diluted with water. The precipitate was filtered off, washed with waterand taken up with EtOAc. The organic layer was washed with a 10% solution ofK2003, water, dried over MgSO4, filtered and the solvent was concentrated under reduced pressure to give 2-(2-(2-((tert-butyldimethylsilyl)oxy)ethoxy)-4-chlorophenyl)-2-((3-methoxy-5-(methylsulfonyl)phenyl)amino)-1 -(6-(trifluoromethoxy)indolin-1-yl)ethanone 6a (1.36 g). The crude compound wasused without purification in the next reaction step.

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