Tributylvinyltin → HCID 69099575, compound

Participants

Reaction Steps

A solution of ethyl 2-[4-(2-{(5-bromopyridin-2-yl)[4-(trifluoromethyl)benzyl]amino}ethyl)phenoxy]-2-methylpropanoate (150 mg; 0.27 mmol) in 2 ml of toluene was treated under nitrogen with tetrakis(triphenylphosphine)palladium (0) (61 mg; 0.053 mmol), vinyltributyltin (252 mg; 0.80 mmol), lithium chloride (34 mg; 0.80 mmol) and 2,6-di-tert-butyl-4-methyl-phenol (3 mg). The mixture was heated at 110C overnight. Upon cooling, the mixture was diluted with 10 ml each of ethyl acetate and water. A saturated solution of KF (10 ml) was added and the phases were separated. The organic phase was washed with brine, dried over sodium sulfate and concentrated. Purification by radial chromatography using an ethyl acetate-hexane gradient (5–50%) afforded ethyl 2-methyl-2-(4-{2-[[4-(trifluoromethyl)benzyl](5-vinylpyridin-2-yl)amino]ethyl}phenoxy)propanoate (71 mg; 52% yield).

Provenance & Evidence