Potassium Carbonate → HCID 90403329, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of Example C5 (0.12 g, 0.33 mmol), 1-ethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (80 mg, 0.36 mmol) and K2CO3 (0.14 g, 0.99 mmol) in dioxane (4 mL) and H2O (1 mL) was sparged with Ar, treated with Pd(PPh3)4 (0.040 g, 0.034 mmol), sparged again with Ar and heated at 90° C. overnight. The mixture was cooled to RT, treated with satd. NaHCO3, extracted with EtOAc (3×) and the combined organics were dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (MeOH/DCM) to obtain N-((5-((2-(1-ethyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)carbamoyl)-2-methoxy-2-methylpropanamide (40 mg, 28%). 1H NMR (400 MHz, DMSO-d6): δ 10.82 (s, 1H), 10.20 (br s, 1H), 8.38 (d, J=5.7 Hz, 1H), 8.31 (s, 1H), 8.27 (d, J=2.9 Hz, 1H), 8.02 (br s, 1H), 7.98 (s, 1H), 7.75 (dd, J=9.0, 2.9 Hz, 1H), 7.24 (d, J=2.4 Hz, 1H), 6.71 (dd, J=5.7, 2.4 Hz, 1H), 4.14 (q, J=7.3 Hz, 2H), 3.21 (s, 3H), 1.37 (t, J=7.3 Hz, 3H), 1.36 (s, 6H); MS (ESI) m/z: 425.2 (M+H+).

Provenance & Evidence