4-Bromoanisole → HCID 69099531, compound

Participants

Reaction Steps

A mixture of 1-(6-{allyl[4-(trifluoromethoxy)benzyl]amino}pyridin-3-yl)ethanone (10 g; 28.5 mmol), 4-bromo-anisole (5.6 g; 29.9 mmol), palladium (II) acetate (0.14 g; 0.63 mmol) and tri-o-tolylphosphine (0.57 g; 1.88 mol) in 11 ml of MeCN and 8 ml of DIEA was heated to reflux overnight. Upon cooling, the mixture was concentrated and the residue partitioned between ethyl acetate and 1N NaOH. The organic phase was dried over sodium sulfate and concentrated. Purification by flash chromatography eluting with dichloromethane afforded 1-(6-{[(2E)-3-(4-methoxyphenyl)prop-2-enyl][4-(trifluoromethoxy)benzyl]amino}pyridin-3-yl)ethanone (7.4 g; 54% yield).

Provenance & Evidence