Potassium Carbonate → HCID 67468307, compound

Participants

Reaction Steps

To a degassed solution of 4-(4-amino-2,5-difluorophenoxy)-3-iodopyridin-2-amine (0.33 g, 0.91 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.28 g, 1.36 mmol) in dioxane (5 ml) was added a degassed solution of K2CO3 (0.37 g, 2.73 mmol) in water (2 mL) and tetrakis(triphenylphosphine)palladium(0) (0.105 g, 0.09 mmol). The resultant mixture was stirred for 16 h at 90° C. Sat. NaHCO3 solution (35 mL) was added. The resultant mixture was extracted with EtOAc (2×30 mL). The combined organics were washed with brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by silica gel chromatography (MeOH/CH2Cl2) to afford 4-(4-amino-2,5-difluorophenoxy)-3-(1-methyl-1H-pyrazol-4-yl)pyridin-2-amine (188 mg, 65.2%) as white solid (188 mg, 65.2% yield). 1H NMR (400 MHz, DMSO-d6): δ 7.85 (s, 1H), 7.70 (d, J=6.0 Hz, 1H), 7.57 (s, 1H), 7.06 (dd, J=11.2 Hz, 7.2 Hz, 1H), 6.66 (dd, J=12.0 Hz, 8.0 Hz, 1H), 5.86 (d, J=5.6 Hz, 1H), 5.60 (s, 2H), 5.39 (s, 2H), 3.85 (s, 3H); MS (ESI) m/z: 318.1 (M+H+).

Provenance & Evidence