(Diethylamino)sulfur trifluoride → HCID 23521698, compound

Participants

Reaction Steps

To a solution of N-(3-(α-hydroxybenzyl)phenyl)-N-(ethylsulfonyl)pyrid-3-ylmethylamine (0.106 g, 2.77 mmol) in DCM was added DAST (0.040 mL, 3.05 mmol). The reaction was stirred overnight and poured into saturated NaHCO3 solution and extracted with EtOAc, dried over MgSO4, filtered, and concentrated. The residue was chromatographed on silica gel with 2:1 DCM/EtOAc to give the title compound as a clear oil. 1H NMR: 8.47 (dd,J=4.9, 1.5 Hz, 1H), 8.33 (d,J=2.0 Hz, 1H), 7.63 (dt,J=7.8, 2.0 Hz, 1H), 7.38-7.28 (m,4H), 7.24-7.16 (m,6H), 4.89 (AofAB,d,J=14.8 Hz, 1H), 4.83 (BofABd,J=14.8 Hz, 1H), 3.07 (q,J=7.3 Hz, 2H), 1.40 (t,J=7.3 Hz, 3H). MS calcd. 384.1; MS (M+1) 385.1.

Provenance & Evidence