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
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.
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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