Potassium Carbonate → HCID 59606547, compound

Participants

Reaction Steps

A mixture of 3-bromo-2-methylpyridine (0.13 mL; 1.16 mmol; 1 eq.), methyl 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (353 mg; 1.28 mmol; 1.1 eq.), potassium carbonate (803 mg; 5.81 mmol; 5 eq.) and tetrakis(triphenylphosphine)palladium(0) (134 mg; 0.12 mmol; 0.1 eq.) in toluene (1 mL) and water (1 mL) was refluxed for 2 hours. The reaction mixture was cooled down to room temperature and filtered through a pad of CELITE which was further washed with toluene (20 mL). The filtrate was concentrated in vacuo and the residue taken up in Ethyl acetate (10 mL). The organic layer was washed with a sat. aq. NaHCO3, water and brine, dried over MgSO4 and concentrated in vacuo. The residue (250 mg; 1.04 mmol; 1 eq.) was taken up in EtOH (7.5 mL) and sodium hydroxide (5M; 0.62 mL; 3.11 mmol; 3 eq.). The reaction mixture was stirred at 60° C. for 2 hours then concentrated in vacuo. The residue was taken up in water (50 mL) and the aqueous phase was washed with Ethyl acetate (2×20 mL) then acidified pH 2 with conc. HCl. The solution was concentrated in vacuo to ca. 15 mL, the precipitate filtered off and washed with ACN to afford the title compound (190 mg, 72%) as a beige solid.

Provenance & Evidence