Sodium Bicarbonate → HCID 23521677, compound

Participants

Reaction Steps

To a suspension of methyltriphenylphosphonium bromide (0.269 g, 0.752) in 3 mL THF at 0° C. was added KHMDS (0.5 M in toluene, 1.5 mL, 0.752 mmol). The mixture was warmed to ambient temperature for 1 h and N-(3-benzoylphenyl)-N-(ethylsulfonyl)pyrid-3-ylmethylamine (0.143 g, 0.376 mmol) as a solution in 3 mL THF was added via cannula. After 3 h the mixture was poured into saturated NaHCO3 solution and Extracted with EtOAc, dried over MgSO4, filtered and concentrated. The residue was chromatographed with 10:1 to 5:1 DCM/EtOAc to give the title compound as a clear oil. 1H NMR: 8.50 (dd,J=4.9, 1.5 Hz, 1H), 8.35 (d,J=2.0 Hz, 1H), 7.70 (dt,J=7.8, 2.0 Hz, 1H), 7.37-7.19 (m,9H), 7.14 (m,1H), 5.48 (d,J=1.0 Hz, 1H), 5.39 (d,J=1.0 Hz, 1H), 4.85 (s,2H), 3.09 (q,J=7.3 Hz, 2H), 1.41 (t,J=7.3 Hz, 3H). MS calcd. 378.1; MS (M+1) 379.1.

Provenance & Evidence