Dichloromethane → HCID 66658923, compound

Participants

Reaction Steps

Stir a solution of (2R)-propane-2-sulfonic acid {2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-amide (50 g, 136.2 mmol), Ethyl 3-Cyano-4-trifluoromethanesulfonyloxy-benzoate (40 g, 123.8 mmol), PdCl2(dppf).DCM (3.03 g, 3.71 mmol) and KOAc (36.43 g, 371.4 mmol) in DME:EtOH:H2O (200 mL/200 mL/200 mL) under nitrogen at 80° C. for 50 minutes. Pour the reaction mixture into ice-water and extract it with EtOAc. Wash the organic layer with water and saturated aq. sodium chloride solution, dry over MgSO4, filter and concentrate it in vacuo. Subject residue to silica gel chromatography eluting with hexane/EtOAc 4:1 to 3:1. Triturate the product in hexane, filter and dry, to yield 37.95 g of 1-(S)-Ethyl 2-Cyano-4′-[1-methyl-2-(propane-2-sulfonylamino)-ethyl]-biphenyl-4-carboxylate (74%). MS(ES): m/z=413.1 [M-H].

Provenance & Evidence