Potassium Carbonate → HCID 90403061, compound

Participants

Reaction Conditions

Reaction Steps

A solution of Example A1 (0.380 g, 1.510 mmol) and 6-(methylamino)-3-pyridinylboronic (0.252 g, 1.661 mmol) in dioxane (8 mL) was sparged with Ar, treated with a solution of K2CO3 (0.417 g, 3.02 mmol) in water (2 mL) and heated at 90° C. for 16 h. The mixture was cooled to RT, treated with water and extracted with EtOAc (2×). The combined organics were washed with brine, dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (MeOH/DCM) to afford N-methyl-4-((6-nitropyridin-3-yl)oxy)-[2,3′-bipyridin]-6′-amine (300 mg, 61%) as an orange amorphous solid. 1H NMR (400 MHz, DMSO-d6): δ 8.73 (d, J=2.5 Hz, 1H), 8.58 (d, J=2.8 Hz, 1H), 8.55 (d, J=5.6 Hz, 1H), 8.39 (d, J=8.9 Hz, 1H), 8.06 (dd, J=8.8, 2.5 Hz, 1H), 7.96 (dd, J=8.9, 2.9 Hz, 1H), 7.61 (d, J=2.3 Hz, 1H), 7.00 (dd, J=5.6, 2.3 Hz, 1H), 6.87 (q, J=5.2 Hz, 1H), 6.48 (d, J=8.8 Hz, 1H), 2.80 (d, J=4.7 Hz, 3H); MS (ESI) m/z: 324.1 (M+H+).

Provenance & Evidence