Nitrogen → HCID 57987541, compound

Participants

Reaction Steps

A mixture of methyl(2-chloropyridin-4-yl)acetate (1.0 g, 5.4 mmol), 4-(trifluoromethoxy)phenylboronic acid (1.67 g, 8.0 mmol) and potassium phosphate (1.7 g, 8.0 mmol) in toluene (15 ml) was degassed, evacuated and N2 filled (×3). [1,1′-bis(diphenylphosphino)ferrocene]dichloro palladium (H), complex with DCM (1:1) (330 mg, 0.4 mmol, 5 mol %) was added and following a further degassing, evacuation and N2 fill (×3), the mixture was heated at reflux for 16 hours. The reaction was cooled to room temperature and diluted with EtOAc (100 ml). The mixture was filtered through a Celite® pad, washing through with EtOAc and the filtrate was evaporated. The residue was purified by chromatography on silica, eluting with 15-20% EtOAc/isohexane to give the ester (1.25 g, 75%) as a pale gum. 1H NMR (400 MHz, CDCl3) δ: 3.70 (2H, s), 3.74 (3H, s), 7.20 (1H, dd, J 1.5, 5.0), 7.31 (2H, d, J 8.8), 7.64 (1H, s), 8.00-8.04 (2H, m), 8.64 (1H, d, J 5.0).

Provenance & Evidence