Category: 959235-95-1

Electric Literature 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.

HATU (7.02 g, 18.46 mmol) was added to a mixture of 6-(trifluoromethoxy)indoline [CAS 959235-95-1 ] (2.5 g, 12.3 mmol), 2-(4-chloro-2-fluorophenyl)acetic acid [CAS 194240-75-0] (2.32 g, 12.3 mmol) and diisopropylethylamine (6.1 ml_, 36.9 mmol) in DMF (100 ml_). The resulting mixture was stirred at room temperature for 12 h. The mixture was diluted with water, the precipitate was filtered off, and washed with water. The residue was taken up with EtOAc and the organic solution was washed with a 10% aqueous solution of K2CO3, brine, dried over MgSO , filtered and the solvent was evaporated under reduced pressure. The residue product was crystallized from diisopropyl ether to give 2-(4-chloro-2- fluorophenyl)-1 -(6-(trifluoromethoxy)indolin-1 -yl)ethanone 10a (4 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-(Trifluoromethoxy)indoline, its application will become more common.

Electric Literature of 959235-95-1, 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. 959235-95-1, name is 6-(Trifluoromethoxy)indoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 2-((3-(4-(fe/t-butoxy)-4-oxobutoxy)-5-nnethoxyphenyl)annino)-2-(2- (2-((fe/t-butyldinnethylsilyl)oxy)ethoxy)-4-chlorophenyl)acetic acid 8d (675 mg, 1.08 mmol) in DMF (6 ml_) were added HATU (617 mg, 1.62 mmol),diisopropylethylamine (536 muIota_, 3.24 mmol) and 6-(trifluoromethoxy)indoline [CAS 959235-95-1] (220 mg, 1.08 mmol). The reaction mixture was stirred at room temperature for 7 days. 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 and water, dried over MgSO4, filtered and the solvent was concentrated under reduced pressure to give terf-butyl 4-(3-((1 -(2-(2-((fe/t-butyldimethylsilyl)oxy)ethoxy)-4-chlorophenyl)-2-oxo- 2-(6-(trifluoromethoxy)indolin-1 -yl)ethyl)amino)-5-methoxyphenoxy)butanoate 8e (385 mg). The compound was used without further purification in the next reaction step.

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.

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, Recommanded Product: 959235-95-1

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).

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959235-95-1, name is 6-(Trifluoromethoxy)indoline, 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. Application In Synthesis of 6-(Trifluoromethoxy)indoline

To a solution of 2-(2-(2-((tert-butyldimethylsilyl)oxy)ethoxy)-4-fluorophenyl)-2-((3- methoxy-5-(methylsulfonyl)phenyl)amino)acetic acid 2d (1 g, 1 .90 mmol) in DMF (10 mL) were added HATU (1 .08 g, 2.84 mmol), diisopropylethylamine (940 pL,5.69 mmol) and 6-(trifluoromethoxy)indoline [CAS 959235-95-1] (385 mg, 1.90 mmol). The reaction mixture was stirred at room temperature for 4 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 K2003 in water, a saturated solution of NaCI in water, water, dried over MgSO4,filtered and the solvent was concentrated under reduced pressure to give 2-(2-(2-((tert-butyld imethyl silyl )oxy)ethoxy)-4-fl uorophenyl )-2-((3-methoxy-5-(methylsulfonyl)phenyl)amino)-1 -(6-(trifluoromethoxy)indolin-1 -yl)ethanone 3a(1 .32 g). The crude compound was used without purification in the next reactionstep.

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

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

HATU (7.02 g, 18.5 mmol) was added to a mixture of 6-(trifluoromethoxy)indoline [CAS 953906-76-8] (2.5 g, 12.31 mmol), 2-(4-chloro-2-fluorophenyl)acetic acid [CAS 194240-75-0] (2.32 g, 12.3 mmol) and diisopropylethylamine (6.1 ml_, 36.9 mmol) in DMF (100 ml_). The resulting mixture was stirred at room temperaure for 12 h. The mixture was diluted with water and the precipitate was filtered off and washed with water. The residue was taken up with EtOAc and the organic layer was washed with a 10% solution of K2CO3 in water, washed with brine, dried over MgSO4, filtered, and the solvent was evaporated under reduced pressure. The crude product was crystallized from diisopropyl ether to give 2- (4-chloro-2-fluorophenyl)-1 -(6-(trifluoromethoxy)indolin-1 -yl)ethanone 6a (4 g).

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

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. 959235-95-1, name is 6-(Trifluoromethoxy)indoline, A new synthetic method of this compound is introduced below., COA of Formula: C9H8F3NO

A mixture of 6-(trifluoromethoxy)indoline [CAS 959235-95-1 ] (2.5 g, 12.3 mmol), 2-(4-chloro-2-methoxyphenyl)acetic acid [CAS 170737-95-8] (2.47 g, 12.3 mmol), HATU (7 g, 18.5 mmol) and diisopropylethylamine (6.1 mL, 36.9 mmol) in DMF (40-mL) was stirred at room temperature for 4 h. Water and EtOAc were added. The organic layer was separated, washed with water, 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 85/15). The pure fractions were combined and the solvent was concentrated under reduced pressure to give, after crystallization from CH3CN/heptane, 2-(4-chloro-2- methoxyphenyl)-1 -(6-(trifluoromethoxy)indolin-1 -yl)ethanone 8a (4.3 g).

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; 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

Reference 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 ] (2.5 g, 12.3 mmol), 2- (4-chloro-2-methoxyphenyl)acetic acid [CAS 170737-95-8] (2.47 g, 12.3 mmol), HATU (7 g, 18.5 mmol) and diisopropylethylamine (6.1 mL, 36.9 mmol) in DMF (40 mL) was stirred at room temperature for 4 h. Water and EtOAc were added. The organic layer was separated, washed with water, 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 85/15). The pure fractions were combined and the solvent was concentrated under reduced pressure to give, after crystallization from CHsCN/heptane, 2-(4-chloro-2- methoxyphenyl)-1 -(6-(trifluoromethoxy)indolin-1 -yl)ethanone 17c (4.3 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-(Trifluoromethoxy)indoline, its application will become more common.

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

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.

To a stirring solution of 2-(4-chloro-2-(4-methoxy-3,3-dimethyl-4- oxobutoxy)phenyl)acetic acid 14b (576 mg, 1 .83 mmol), 6- (trifluoromethoxy)indoline [CAS 959235-95-1 ] (409 mg, 2.01 mmol) anddiisopropylethylamine (907 muIota_, 5.49 mmol) in DMF (7.5 ml_) under N2-atm was added HATU (1 .07 g, 2.75 mmol), and the reaction mixture was stirred at room temperature for 5 h. Water (30 ml_) was added, and the product was extracted (2x) with Et2O. The combined organic layers were washed with brine, dried overMgSO4, filtered, and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (40 g) using a gradient of heptane/EtOAc 100/0 to 0/100. The desired fractions were combined and evaporated under reduced pressure, and co-evaporated with toluene. The residue was dried under vacuum at 45C to provide methyl 4-(5-chloro-2-(2-oxo-2-(6- (trifluoromethoxy)indolin-1 -yl)ethyl)phenoxy)-2,2-dimethylbutanoate 14c (790 mg) as a powder.

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

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

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., HPLC of Formula: C9H8F3NO

A mixture of 6-(trifluoromethoxy)indoline [CAS 959235-95-1] (1.85 g, 9.12 mmol),2-(2-(2-(benzyloxy)ethoxy)-4-ch lorophenyl )-2-((3-methoxy-5-(methylsulfonyl)phenyl)amino)acetic acid 6d (5.69 g, 10.9 mmol), HATU (5.2 g,13.7 mmol) and diisopropylethylamine (4.52 mL, 27.4 mmol) in DMF (40 mL) wasstirred at room temperature for 2 h. The mixture was diluted with water. The precipitate was filtered off and washed with water. The precipitate was taken up with EtOAc, washed with a 10% solution of K2003 in water, water, dried over MgSO4, filtered and the solvent was evaporated under reduced pressure. Purification was performed by flash chromatography on silica gel (15-40 pm, 220 g, heptane/EtOAc 70/30). The pure fractions were combined and concentrated to dryness to give 2-(2-(2-(benzyloxy)ethoxy)-4-ch lorophenyl )-2-((3-methoxy-5- (methylsulfonyl )phenyl)am ino)-1 -(6-(trifluoromethoxy)indol in-i -yl)ethanone 6e (5.6 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; 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

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., Safety of 6-(Trifluoromethoxy)indoline

HATU (1 .54 g, 4.06 mmol) was added to a mixture of 6-(trifluoromethoxy)indoline [CAS 953906-76-8] (550 mg, 2.70 mmol), 2-(4-chloro-2-fluorophenyl)-2-((3- (2-hydroxyethoxy)-5-methoxyphenyl)amino)acetic acid 2e (1 g, 2.70 mmol) and diisopropylethylannine (1 .34 mL, 8.1 1 mmol) in DMF (30 mL). The resulting mixture was stirred at room temperature for 12 h. The mixture was diluted with water. The precipitate was filtered off, and washed with water. The solid was dissolved in EtOAc, washed with a 10% solution of K2CO3 in water and then with brine. The organic layer was dried over MgSO4, filtered, and the solvent was evaporated under reduced pressure. The crude residue was purified by flash chromatography on silica gel (15-40 muetaeta, 80 g, CH2CI2/MeOH 99.5/0.5) to afford 2-(4-chloro-2-fluorophenyl)-2-((3-(2-hydroxyethoxy)-5-methoxyphenyl)amino)-1 -(6-(trifluoro- methoxy)indolin-1 -yl)ethanone (Compound 6, 500 mg). An analytical sample of Compound 6 was obtained by crystallized from diisopropyl ether. Compound 6: 1H NMR (500 MHz, DMSO-cfe) delta ppm 3.14 – 3.22 (m, 2 H) 3.58 – 3.68 (m, 5 H) 3.80 – 3.90 (m, 2 H) 4.05 – 4.15 (m, 1 H) 4.38 – 4.47 (m, 1 H) 4.80 (t, J=5.5 Hz, 1 H) 5.70 (d, J=9.1 Hz, 1 H) 5.79 (t, J=1 .9 Hz, 1 H) 5.93 (d, J=1 .9 Hz, 2 H) 6.63 (d, J=9.1 Hz, 1 H) 7.03 (dd, J=8.2, 1 .6 Hz, 1 H) 7.31 – 7.37 (m, 2 H) 7.42 – 7.51 (m, 2 H) 8.02 (s, 1 H) LC/MS (method LC-A): Rt 3.39 min, MH+ 555 Melting point: 166C

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; 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