Cesium carbonate → 6-(3-(Trimethylsilyl)phenyl)picolinaldehyde

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-bromopicolinaldehyde (1.00 g, 5.38 mmol) in dioxane (25 mL) at ambient temperature was added 3-trimethylsilylphenylboronic acid (1.04 g, 5.38 mmol), cesium carbonate (2.7 mL, 5.4 mmol) and 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (0.088 g, 0.11 mmol). The solution was degassed (3× vacuum/purge N2) and heated to 80° C. overnight. The mixture was cooled to room temperature and partioned between water and CH2Cl2. The organic phase concentrated and purified by chromatography (10% EtOAc:hexanes) to provide 1.18 g (86%) of the title compound. MS (DCI30 ) m/z 256 (M+H).

Provenance & Evidence