Potassium Carbonate → N-(5-((2-(1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)-2-oxo-3-(tetrahydro-2H-pyran-4-yl)imidazolidine-1-carboxamide

Participants

Reaction Conditions

Reaction Steps

A mixture of Example C1 (0.15 g, 0.359 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.077 g, 0.395 mmol), and K2CO3 (0.198 g, 1.436 mmol) in 4:1 dioxane/water (5 mL) was sparged with Ar, treated with Pd(PPh3)4 (0.041 g, 0.036 mmol), sparged again with Ar and heated at 80° C. overnight. The mixture was cooled to RT, treated with brine, extracted with EtOAc (2×) and the combined organics were dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (MeOH/DCM). The material was treated with Et2O, allowed to stand at RT and the resulting solid collected via filtration to afford N-(5-((2-(1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)-2-oxo-3-(tetrahydro-2H-pyran-4-yl)imidazolidine-1-carboxamide (80 mg, 48%). 1H NMR (400 MHz, DMSO-d6): δ 13.04 (s, 1 H), 10.96 (s, 1 H), 8.37 (d, J=5.7 Hz, 1 H), 8.32 (s, 1 H), 8.23 (d, J=2.9 Hz, 1 H), 8.07 (d, J=9.0 Hz, 1 H), 8.02 (s, 1 H), 7.71 (dd, J=9.0, 2.9 Hz, 1 H), 7.32 (d, J=2.4 Hz, 1 H), 6.67 (dd, J=5.7, 2.4 Hz, 1 H), 3.91-3.80 (m, 5 H), 3.40 (m, 4 H), 1.71 (m, 2 H), 1.59 (m, 2 H); MS (ESI) m/z: 450.2 (M+H+).

Provenance & Evidence