(Diethylamino)sulfur trifluoride → HCID 68181728, compound

Participants

Reaction Steps

To a solution of 2-[1-(2-aminopyrimidin-4-yl)-6-bromo-1H-indazol-3-yl]propan-2-ol (200 mg, 0.57 mmol) in dry DCM (2 mL) at 0° C. under an atmosphere of nitrogen was introduced (diethylamino)sulphur trifluoride (0.14 mL, 1.15 mmol). The reaction was left to warm to RT for 1 hr. Following addition of sodium bicarbonate (5 mL of a saturated aqueous solution), the reaction mixture was washed with DCM (2×5 mL), and the combined organic extracts dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by flash chromatography (Biotage, eluent heptane:EtOAc [0-100%] gradient) to furnish the title compound as a yellow solid: 1H NMR (500 MHz, CDCl3) delta 1.81-1.97 (6H, m), 5.18 (2H, br. s.), 7.28 (1H, s), 7.40-7.50 (1H, m), 7.78-7.92 (1H, m), 8.32 (1H, d, J=5.67 Hz), 9.01 (1H, d, J=1.10 Hz); LC-MS: m/z=+349.95/351.80 (M+H)+.

Provenance & Evidence