Cesium carbonate → HCID 86270409, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of Example C8 (0.200 g, 0.426 mmol), N,N-dimethyl urea (0.225 g, 2.56 mmol), Cs2CO3 (0.347 g, 1.065 mmol) and Xantphos (0.074 g, 0.128 mmol) in dioxane (3 mL) was sparged with Ar, treated Pd2(dba)3 (0.051 g, 0.055 mmol), sparged again with Ar and heated at 100° C. overnight. The mixture was cooled to RT, treated with brine, extracted with EtOAc (3×) and the combined organics were dried over Na2SO4, concentrated to dryness and purified twice via silica gel chromatography (MeOH/DCM, then MeOH/EtOAc). The material was suspended in 1:1 EtOAc/Et2O, sonicated and the resulting solid collected via filtration to afford N-(5-chloro-4-((2-(3,3-dimethylureido)pyridin-4-yl)oxy)-2-fluorophenyl)-2-oxo-3-(tetrahydro-2H-pyran-4-yl)imidazolidine-1-carboxamide (98 mg, 44%). 1H NMR (400 MHz, DMSO-d6): δ 10.92 (d, J=2.7 Hz, 1 H), 8.91 (s, 1 H), 8.39 (d, J=8.0 Hz, 1 H), 8.10 (d, J=5.7 Hz, 1 H), 7.56 (d, J=11.2 Hz, 1 H), 7.34 (d, J=2.4 Hz, 1 H), 6.56 (dd, J=5.7, 2.4 Hz, 1 H), 3.93-3.86 (m, 3 H), 3.83-3.81 (m, 2 H), 3.47 (m, 2H), 3.37 (m, 2 H), 2.87 (s, 6 H), 1.71 (m, 2 H), 1.59 (m, 2H); MS (ESI) m/z: 521.2 (M+H+).

Provenance & Evidence