Ethyl isocyanate → HCID 59806015, compound

Participants

Reaction Steps

A solution of 161 (100 mg, 0.25 mmol) and ethyl isocyanate (29 μL, 28 mg, 0.375 mmol) in dichloromethane (5 mL) was treated with tin(II) 2-ethylhexanoate (44 μL, 55 mg, 0.135 mmol). The reaction mixture was stirred overnight at r.t. under nitrogen, concentrated and the residue was purified by flash chromatography using gradient 70 to 90% EtOAc in hexanes as an eluent. The material obtained was then dissolved in 2:1 mixture of dichloromethane and TFA (3 mL), stirred for 30 min and concentrated. The residue was then dissolved in EtOAc (5 mL) and washed with saturated NaHCO3 solution (5 mL), dried over Na2SO4, filtered and concentrated to afford title compound 162 (39 mg, 42% yield). 1H NMR: CDCl3 δ(ppm): 7.7 (d J=8.8 Hz, 2H), 7.6 (s, 1H), 7.2 (d, J=7.6 Hz, 1H), 7.0 (t, J=8.8 Hz, 1H), 6.8 (t, J=7.8 Hz, 2H), 6.5 (d, J=8.8 Hz, 2H), 5.3 (s, 1H), 4.6 (s, 1H), 3.9 (s, 2H), 3.6 (m, 1H), 3.4 (m, 3H), 3.1 (m, 2H), 2.2 (m, 2H), 1.2 (s, 1H), 1.1 (m, 3H). LRMS (ESI): (calc) 368.18 (found) 369.1 (MH+).

Provenance & Evidence