Hydrochloric Acid → HCID 117965908, compound

Participants

Reaction Steps

30.0 g (60.7 mmol) [(S)-6-((R)-4-bromo-7-fluoroindan-1-yloxy)-2,3-dihydrobenzo-furan-3-yl]-acetic acid morpholine salt is dissolved in 480 ml EtOH/water (1:1) and 6.30 ml conc. HCl (64.0 mmol, 37%) is added. The mixture is heated to reflux and stirred for 30 min. After cooling in an ice bath the suspension is filtered off, washed with cold water and dried to yield [(S)-6-((R)-4-bromo-7-fluoroindan-1-yloxy)-2,3-dihydrobenzo-furan-3-yl]-acetic acid. b) Under argon, 30.0 g (73.7 mmol) [(S)-6-((R)-4-bromo-7-fluoroindan-1-yloxy)-2,3-dihydrobenzo-furan-3-yl]-acetic acid, 20.6 g (81.0 mmol) bis(pinacolato)diboron and 16.3 g (166 mmol) potassium acetate are suspended in 150 ml 2-methyltetrahydrofuran. The mixture is degassed and 165 mg (0.74 mmol) palladium(II) acetate and 528 mg (1.47 mmol) di(1-adamantyl)-n-butylphosphine are added. The mixture is degassed again and heated to 80° C. until completion of the reaction. Then, 150 ml water is added at 70° C. The aqueous phase is separated and the organic phase is cooled to r.t. and stirred overnight. The resulting suspension is cooled to 0° C. and 75 ml MCH is added. The crude product is filtered off, washed with cold 2-methyltetrahydrofuran/methylcyclohexane (2:1) and cold methylcyclohexane and dried. Further purification is achieved by recrystallization from 2-methyltetrahydrofuran or suspending the product in methylcyclohexane. Yield: 24.4 g; Rf=0.69 (PE/EtOAc/AcOH=0.69); Mass spectrum (ESI): m/z=455 [M+H]+.

Provenance & Evidence