Cesium carbonate → HCID 86671316, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-bromopicolinaldehyde (4.07 g, 21.88 mmol) in dioxane (40 mL) at ambient temperature was added 4-butoxy-3-chlorophenylboronic acid (5.00 g, 21.9 mmol), 2M cesium carbonate (22.0 mL, 43.8 mmol) and 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (0.357 g, 0.438 mmol). The mixture was degassed (3× vacuum/purge N2) then heated at 80° C. overnight. The mixture was cooled to room temperature then partioned between water and CH2Cl2. The organic phase was concentrated and purified by chromatography (silica gel, 10% ethyl acetate:hexanes) to provide 5.20 g (82%) of the title compound. MS (DCI+) m/z 290 (M+H).

Provenance & Evidence