Triethylsilane → HCID 71558621, compound

Participants

Reaction Steps

To a solution of bis(tert-butyl (5-(2-(4-(N-benzyl-N-(pyrimidin-2-yl)sulfamoyl)-2,5-difluorophenoxy)-5-chlorophenyl)benzo[d]isoxazol-3-yl))carbamate (2.03 g, 2.47 mmol) in trifluoroacetic acid (50 mL) were added triethylsilane (2.0 mL, 13 mmol) and trifluoromethanesulfonic acid (0.5 mL). This mixture was heated at reflux for 5 h and allowed to cool to ambient temperature. The mixture was concentrated in vacuo to afford a brown residue that was triturated in diethyl ether (40 mL) to afford 4-(2-(3-aminobenzo[d]isoxazol-5-yl)-4-chlorophenoxy)-2,5-difluoro-N-(pyrimidin-2-yl)benzenesulfonamide as an off-white solid in 72% yield (0.95 g): 1H NMR (300 MHz, 5% D2O in DMSO-d6) δ 8.35 (d, J=4.9 Hz, 2H), 7.90 (s, 1H), 7.72 (dd, J=9.9, 6.6 Hz, 1H), 7.58-7.55 (m, 2H), 7.47 (dd, J=8.7, 2.3, 1H), 7.37 (d, J=8.7 Hz, 1H), 7.25 (d, J=8.7 Hz, 1H), 6.96 (t, J=4.8 Hz, 1H), 6.90 (dd, J=10.3, 6.6 Hz, 1H) (NH not observed); MS (ES+) m/z 529.6 (M+1), 531.5 (M+1).

Provenance & Evidence