2-Bromopyridine → Methyl 2,4-dichloro-5-(pyridin-2-yl)benzoate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 2,4-dichloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (Preparation 45, 5 g, 15 mmol) in dioxane (30 mL) and water (10 mL) was added 2-bromopyridine (1.73 mL, 18 mmol), tetrakis(triphenylphosphine)palladium (0) (1.75 g, 1.51 mmol) and potassium carbonate (4.18 g, 30 mmol). The reaction was heated to 110° C. The reaction was cooled, extracted into EtOAc and separated. The organic layer was washed with brine, dried over magnesium sulphate and concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with 10-50% EtOAc in heptanes followed by trituration with TBME to afford the title compound (3.96 g, 93%).

Provenance & Evidence