N,N'-Dimethylethylenediamine → (S,E)-tert-butyl 4-(4-(5,6-dichloro-1-oxo-3,4-dihydroisoquinolin-2(1H)-yl)styryl)-2,2-dimethyloxazolidine-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

A stirred suspension of (S)-4-[(E)-2-(4-iodo-phenyl)-vinyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (300 mg, Example 3a), 5,6-dichloro-3,4-dihydro-2H-isoquinolin-1-one (204 mg), copper(I) iodide (13 mg), N,N′-dimethylethylenediamine (15 μl) and potassium phosphate (356 mg) in toluene (3 ml) in a sealed tube was heated at 120° C. overnight. The mixture was then cooled to room temperature and was purified by column chromatography (SiO2; gradient: heptane/EtOAc) to give (S,E)-tert-butyl 4-(4-(5,6-dichloro-1-oxo-3,4-dihydroisoquinolin-2(1H)-yl)styryl)-2,2-dimethyloxazolidine-3-carboxylate (221 mg, 61%) as a yellow amorphous solid. MS (ISP): 541.2 ([{37Cl35Cl}M+Na]+), 539.2 ([{35Cl}M+Na]+), 519.3 ([{37Cl35Cl}M+H]+), 517.2 ([{35Cl}M+H]+), 463.2 ([{37Cl35Cl}M+H—C4H8]+), 461.2 ([{35Cl}M+H—C4H8]+), 419.2 ([{37Cl35Cl}M+H—C4H8—CO2]+), 417.2 ([{35Cl}M+H—C4H8—CO2]+).

Provenance & Evidence