Potassium Carbonate → HCID 90403630, compound

Participants

Reaction Conditions

Reaction Steps

A solution of Example A1 (0.525 g, 2.086 mmol) and 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (0.551 g, 2.504 mmol) in dioxane (16 mL) was sparged with Ar, treated with a solution of K2CO3 (0.577 g, 4.17 mmol) in water (4 mL) and heated at 90° C. for 1 h. The mixture was cooled to RT, treated with water and extracted with EtOAc (3×). The combined organics were washed with brine, dried over Na2SO4 and concentrated to dryness. The material was treated with 60% EtOAc/Hex, sonicated and the resulting solid collected via filtration to afford 4-((6-nitropyridin-3-yl)oxy)-[2,3′-bipyridin]-6′-amine (580 mg, 90%) as a dark orange solid. 1H NMR (400 MHz, DMSO-d6): δ 8.66 (d, J=2.5 Hz, 1H), 8.58 (d, J=2.8 Hz, 1H), 8.55 (d, J=5.6 Hz, 1H), 8.40 (dd, J=8.9, 0.5 Hz, 1H), 8.06 (dd, J=8.7, 2.5 Hz, 1H), 7.96 (dd, J=8.9, 2.8 Hz, 1H), 7.61 (d, J=2.3 Hz, 1H), 7.02 (dd, J=5.6, 2.3 Hz, 1H), 6.48 (dd, J=8.7, 0.7 Hz, 1H), 6.32 (s, 2H); MS (ESI) m/z: 310.1 (M+H+).

Provenance & Evidence