Dimethyl Sulfoxide → HCID 85789461, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of DMSO (0.190 mL, 2.68 mmol) in 4 mL DCM at −78° C. was added oxalyl chloride (0.146 mL, 1.67 mmol) dropwise. After 15 min a solution of N-(4-(hydoxymethyl)phenyl)-N-(ethanesulfonyl)pyrid-3-ylmethylamine (0.241 g, 0.669 mmol) was added via cannula. The reaction was stirred for 30 min and triethylamine (0.932 mL, 6.69 mmol) was added and warmed to 0° C. over 1 h. The mixture was poured into saturated NaHCO3 solution and diluted with ether. The organic layer was washed with H2O and brine, dried over MgSO4, filtered, and concentrated. The residue was chromatographed on silica gel with 5:1 DCM/EtOAc to give 173 mg of a clear oil (72%). 1H NMR: 9.97 (s,1H), 8.50 (dd,J=4.9, 1.5 Hz, 1H), 8.35 (d,J=2.0 Hz, 1H), 7.87 (m,2H), 7.66 (dt,J=7.8, 2.0 Hz, 1H), 7.44 (m,2H), 7.24 (ddd,J=7.8, 4.9, 1.0 Hz, 1H), 4.97 (s,2H), 3.84 (q,J=9.3 Hz, 2H).

Provenance & Evidence