Sodium Carbonate → 1-{3-[7-(4-Fluoro-phenyl)-imidazo[1,2-a]pyridin-3-yl]-phenyl}-3-(2,2,2-trifluoro-ethyl)-urea

Temperature

80 °C

A mixture of 7-(4-fluoro-phenyl)-3-iodo-imidazo[1,2-a]pyridine (10.1 g, 29.8 mmol), 1-(3-bromo-phenyl)-3-(2,2,2-trifluoro-ethyl)-urea (12.3 g, 35.8 mmol) and 2M sodium carbonate (120 mL) in dimethoxyethane (595 mL) was deoxygenated by evacuation/refill with N2 (×3). Tetrakis(triphenylphosphine)palladium (1.72 g, 1.49 mmol) was added, the resulting mixture was deoxygenated again (×3) and then heated at 80° C. under N2 overnight. The reaction was allowed to cool to RT, and solvents were removed under reduced pressure. The crude mixture was diluted with water (100 mL), EtOAc (100 mL) and DCM (100 mL) with stirring. The resulting slurry was filtered, the solid was washed with EtOAc and dried under vacuum to give the title compound (9.8 g). 1H NMR (400 MHz, DMSO-d6) δ 8.98 (1H, s), 8.61 (1H, d), 7.99 (1H, s), 7.96-7.87 (2H, m), 7.79 (2H, s), 7.45 (2H, d), 7.41-7.30 (3H, m), 7.30-7.23 (1H, m), 6.87 (1H, bt), 4.00-3.89 (2H, m). MS: [M+H]+ 429

1. customwas deoxygenated by evacuation/refill with N2 (×3)
2. customthe resulting mixture was deoxygenated again (×3)
3. temperatureto cool to RT
4. customsolvents were removed under reduced pressure
5. additionThe crude mixture was diluted with water (100 mL), EtOAc (100 mL) and DCM (100 mL)
6. filtrationThe resulting slurry was filtered
7. washthe solid was washed with EtOAc
8. customdried under vacuum

ORD record

ord-6ca39044fa4d4fa8b185b2d127ad17e2

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08895745B2