4-(2,5-Difluoro-4-nitrophenoxy)-3-iodo-2-[bis[(1,1-dimethylethoxy)-carbonyl]amino]pyridine → 4-(2,5-Difluoro-4-aminophenoxy)-3-iodo-2-[bis[(1,1-dimethylethoxy)carbonyl]amino]pyridine

Participants

Reaction Steps

Palladium hydroxide on carbon (0.193 g, 0.275 mmol) (contains 60% water) was added to a solution of 4-(2,5-difluoro-4-nitrophenoxy)-3-iodo-2-[bis[(1,1-dimethylethoxy)-carbonyl]amino]pyridine (1.63 g, 2.75 mmol) in EtOAc (20 mL) and the mixture was hydrogenated (50) psi for 16 h. The completed reaction mixture was filtered through Celite® rinsing forward with EtOAc (2×10 mL). The combined filtrate was concentrated to afford 4-(2,5-difluoro-4-aminophenoxy)-3-iodo-2-[bis[(1,1-dimethylethoxy)carbonyl]amino]pyridine as colorless foam (1.5 g, 97% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.21 (dd, J=7.6 Hz, 5.6 Hz, 1H), 7.24 (dd, J=11.0 Hz, 7.4 Hz, 1H), 6.71 (m, 1H), 6.57 (d, J=5.6 Hz, 1H), 5.55 (s, 2H), 1.35 (s, 18H); MS (ESI) m/z: 564.1 (M+H+).

Provenance & Evidence