Water → HCID 66591140, compound

Participants

Reaction Conditions

Reaction Steps

278 mg (1.20 mmol, 1.5 eq) of methyl 3-(5-bromofuran-2-yl)acrylate and 300 mg (0.80 mmol, 1.0 eq) of octanoylmethyl-[3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)benzyl]amide (prepared as in 1e) are dissolved in 5 ml of a 5/1 mixture of dimethylformamide and of 2M potassium phosphate solution. 46 mg (0.04 mmol, 5 mol %) of tetrakis(triphenylphosphine)palladium are added and the reaction mixture is then stirred for 2 hours at 80° 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 60/40 heptane/ethyl acetate). 250 mg of methyl 3-(5-{3-[(methyloctanoylamino)methyl]phenyl}furan-2-yl)acrylate are obtained. Yield=78%.

Provenance & Evidence