Potassium Carbonate → HCID 67468806, compound

Participants

Reaction Conditions

Reaction Steps

To a degassed solution of 4-(2,5-difluoro-4-aminophenoxy)-3-iodo-2-[bis[(1,1-dimethylethoxy)carbonyl]amino]pyridine (0.7 g, 1.24 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.52 g, 2.48 mmol) in dioxane (15 mL) was added K2CO3 (0.51 g, 3.7 mmol) in water (3 mL). Tetrakis (triphenylphosphine)Palladium(0) (0.14 g, 0.12 mmol) was added and the reaction mixture was stirred at 100° C. for 3 h. The mixture was diluted with water (40 mL) and EtOAc (50 mL). The layers were separated, and the aq. layer was extracted with EtOAc (20 mL). The combined organics were washed with brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by silica gel chromatography (EtOAc-hexanes) to afford 4-(4-amino-2,5-difluorophenoxy)-3-(1-methyl-1H-pyrazol-4-yl)-2-[bis[(1,1-dimethylethoxy)carbonyl]amino]pyridine as a colorless foam (0.52 g, 81% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.17 (d, J=5.6 Hz, 1H), 7.84 (s, 1H), 7.48 (d, J=0.8 Hz, 1H), 7.21 (dd, J=11.2 Hz, 7.6 Hz, 1H), 6.70 (m, 2H), 5.50 (s, 2H), 3.86 (s, 3H), 1.25 (s, 18H); MS (ESI) m/z: 518.3 (M+H+).

Provenance & Evidence