Cesium carbonate → HCID 86622858, compound

Participants

Reaction Conditions

Reaction Steps

Place 7-chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethanesulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (5 g, 11.7 mmol) in toluene (100 mL) with 3-(2-phenyl-[1,3]dioxolan-2-yl)-propylamine (4.85 g, 23.4 mmol), tris(dibenzylideneacetone)dipalladium (0) (1.1 g, 1.17 mmol), racemic 2,2′-bis(diphenylphosphino)-1,1′-binapthyl (5.1 g, 8.19 mmol), palladium acetate (525 mg, 2.34 mmol) and cesium carbonate (5.34 g, 16.38 mmol). Heat for 16 h at 95° C. in a sealed tube. Cool the reaction to RT, dilute with EtOAc (600 mL) and filter. Concentrate the filtrate and chromatograph on silica gel, eluting with 10:90 to 25:75 EtOAc:hexanes to give the title compound contaminated with some colored impurities. Dissolve the residue in 20:80 EtOAc:hexanes (100 mL) and filter to remove solids. Chromatograph the filtrate on silica gel, eluting with 10:90 EtOAc:hexanes to give the title compound as an orange oil (4.32 g, 76%).

Provenance & Evidence