Sodium Carbonate → HCID 86695028, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of [6-fluoro-3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-naphthalen-2-yl]-acetic acid methyl ester (0.130 g, 0.36 mmol), 2-bromo-5-methanesulfonylpyridine (0.086 g, 0.36 mmol), [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II) (0.005 g, 0.0068 mmol), and 1.0 M aqueous sodium carbonate (0.4 mL, 0.4 mmol) in 1:1 THF-toluene (4 mL) was heated at 80° C. for 20 hours. The reaction mixture was cooled to room temperature, and diluted with ethyl acetate. The resulting mixture was washed with water. The organic layer was dried (Na2SO4), filtered, and concentrated to give an oily yellow solid. Flash chromatography (40 g Analogix column, 5-60% ethyl acetate in hexanes) gave [6-fluoro-4-(5-methanesulfonyl-pyridin-2-yl)-3-methyl-naphthalen-2-yl]acetic acid methyl ester (0.014 g, 10%) as a solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.27 (d, J=3.00 Hz, 1 H), 8.49 (dd, J=8.00, 3.00 Hz, 1 H), 8.04 (dd, J=8.80, 6.60 Hz, 1 H), 7.97 (s, 1 H), 7.73 (d, J=9.00 Hz, 1 H), 7.41 (td, J=8.00, 3.20 Hz, 1 H), 6.72-6.78 (m, 1 H), 3.97-3.99 (m, 2 H), 3.65 (s, 3 H), 3.46 (s, 3 H), 2.05 (s, 3 H).

Provenance & Evidence