Sodium Carbonate → HCID 178425199, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-((3-bromophenoxy)methyl)-N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)benzamide (80 mg, 0.18 mmol), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (40 mg, 0.43 mmol) and sodium carbonate (75 mg, 0.7 mmol), tetra(triphenylphosphine) palladium (23 mg, 0.02 mmol) in 1,4-dioxane (8 ml) and water (2 ml) was stirred for 15 hours at 90° C. under nitrogen atmosphere. After cooling to room temperature, the reaction mixture was concentrated to give a residue. The residue was purified by column chromatography (silica gel, dichloromethane/methanol=20:1) to give product 4-((3-(6-aminopyridin-3-yl)phenoxy)methyl)-N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)benzamide (30 mg, 37%) as a white solid. LRMS (M+H+) m/z: calcd 454.20. found 454. HPLC purity (214 nm): 97%. 1H NMR (300 MHz, d6-DMSO): δ 11.45 (s, 1H), 8.34 (t, J=4.5 Hz, 1H), 8.22 (s, 1H), 7.85-7.83 (m, 2H), 7.73-7.69 (m, 1H), 7.51-7.48 (m, 2H), 7.32-7.12 (m, 3H), 6.91-6.88 (m, 1H), 6.52 (d, J=8.7 Hz, 1H), 6.16 (s, 2H), 5.85 (s, 1H), 5.20 (s, 2H), 4.29 (d, J=4.5 Hz, 2H), 2.16 (s, 3H), 2.10 (s, 3H).

Provenance & Evidence