Potassium Carbonate → HCID 86270219, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of Example C8 (0.200 g, 0.426 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.124 g, 0.639 mmol) and K2CO3 (0.177 g, 1.279 mmol) in dioxane (4 mL) and water (1 mL) was sparged with Ar, treated with Pd(PPh3)4 (0.025 g, 0.021 mmol), sparged again with Ar and heated at 80° C. overnight. The mixture was cooled to RT, treated with satd. NaHCO3, extracted with EtOAc (2×) and the combined organics were washed with brine, dried over MgSO4, concentrated to dryness and purified via silica gel chromatography (MeOH/DCM) to afford N-(4-((2-(1H-pyrazol-4-yl)pyridin-4-yl)oxy)-5-chloro-2-fluorophenyl)-2-oxo-3-(tetrahydro-2H-pyran-4-yl)imidazolidine-1-carboxamide (160 mg, 75%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 13.05 (s, 1H), 10.91 (d, J=2.7 Hz, 1 H), 8.40 (1H, d, J=8.1 Hz, 1 H), 8.36 (d, J=5.7 Hz, 1 H), 8.33 (s, 1 H), 8.04 (s, 1 H), 7.57 (d, J=11.2 Hz, 1 H), 7.30 (d, J=2.5 Hz, 1 H), 6.61 (dd, J=5.7, 2.5 Hz, 1 H), 3.94-3.77 (m, 5 H), 3.47 (t, J=8.2 Hz, 2 H), 3.37 (t, J=11.8 Hz, 2 H), 1.75-1.64 (m, 2 H), 1.59 (m, 2H); MS (ESI) m/z: 501.1 (M+H+).

Provenance & Evidence