Water → HCID 66591177, compound

Participants

Reaction Conditions

Reaction Steps

1.25 g (4.13 mmol, 1.2 eq) of ethyl 3-[4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenyl]acrylate and 1.0 g (3.48 mmol, 1 eq) of tert-butyl (6-bromopyrid-2-yl)-methylcarbamate are dissolved in 15 ml of a 6/1 mixture of dimethylformamide and of 2M potassium phosphate solution. 200 mg (0.173 mmol, 5 mol %) of tetrakis(triphenylphosphine)palladium are added. The mixture is stirred for 3 hours at 90° C. The reaction is stopped by adding 30 mL of water and is then extracted with ethyl acetate. The organic phases are combined and dried over sodium sulfate. The solvents are evaporated off and the residue is then chromatographed on silica gel (80/20 to 70/30 heptane/ethyl acetate). 850 mg of ethyl 3-{4-[6-(tert-butoxycarbonylmethylamino)pyrid-2-yl]phenyl}acrylate are obtained. Yield=64%.

Provenance & Evidence