Cesium carbonate → HCID 66855068, compound

Participants

Reaction Conditions

Reaction Steps

Dissolve (S)-pyrrolidin-3-yl-carbamic acid tert-butyl ester (1.49 g, 8 mmol) in toluene (20 mL). Heat to 110° C. and add 5-bromo-2-fluoropyridine (824 μL, 8 mmol), cesium carbonate (3.9 g, 12 mmol), rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (748 mg, 1.2 mmol) and tris(dibenzylidineacetone)dipalladium(0) (733 mg, 0.8 mmol). Place a nitrogen inlet and condenser on the flask and heat at reflux overnight. Cool and filter the reaction mixture through a pad of Celite® and wash the pad with dichloromethane. Concentrate and chromatograph twice on silica gel, eluting with 0:100 to 25:75 ethyl acetate:dichloromethane, then 10:90 to 40:60 ethylacetate:hexanes, to give (S)-[1-(6-fluoropyridin-3-yl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester as a brown solid (1.54 g, 68%).

Provenance & Evidence