Dichloromethane → HCID 178445723, compound

Participants

Reaction Steps

(R)-4-[5-Bromo-6-(4-tert-butyl-cyclohexyloxy)-naphthalen-2-yl]-4-methyl-oxazolidin-2-one (0.2047 g, 0.0004446 mol), cyclopropyl trifluoroborate potassium salt (0.0658 g, 0.000445 mol), [1,1′Bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (1:1) (0.03 g, 0.00004 mol) and cesium carbonate (0.434 g, 0.00133 mol) were added to a capped 40 mL vial equipped with a magnetic stir bar. The vial was degassed and purged with nitrogen. tetrahydrofuran (5.00 mL, 0.0616 mol) and water (0.50 mL, 0.028 mol) were added and the reaction mixture was stirred at reflux for 24 h under a nitrogen atmosphere. HPLC analysis showed that the reaction was complete. The reaction mixture was cooled to room temperature, diluted with water (10 mL) and extracted with ethylacetate. The combined organic extracts were washed with 1N HCl (20 mL) and brine (20 mL) and then dried over magnesium sulfate. The solvent was removed under vacuum and the crude product was purified by silica gel chromatography (0-50% EtOAc in hexanes) to give 109.3 mg of the title compound (58% yield).

Provenance & Evidence