Water → HCID 73013037, compound

Participants

Reaction Conditions

Reaction Steps

5-Bromo-6-chloro-3-pyridinecarboxylic acid methyl ester (42.2 g, 0.169 mol, CA 78686-77-8) was dissolved in toluene (840 mL). To this solution was added with stirring [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) CH2Cl2 (6.9 g, 8.4 mmol), 4-chlorophenylboronic acid (27.2 g, 0.169 mol) and sodium carbonate solution (2M, 170 mL). This mixture was heated to 90° C. for 1 h and cooled to room temperature. Water (400 mL) was added, the phases were separated and the water mixture was extracted with ethylacetate. Organic phases were pooled, dried with MgSO4 and the volatiles removed in vacuo. The residue was purified by flash chromatography (SiO2, heptane/CH2Cl2) to give the title compound (30.9 g) as a white solid; MS (EI) 281.1, 283.0 (M)+.

Provenance & Evidence