Stannous Chloride → HCID 16718547, compound

Participants

Reaction Steps

To a solution of the alkyne 410 (200 mg, 0.64 mmol) in MeOH (10 ml) was added SnCl2×2H2O (574 mg, 4 eq, 2.54 mmol) and the reaction mixture was heated to reflux for 3 hours. It was then cooled to RT, concentrated and crude amine 411 was used directly in the next step with no additional purification (182 mg, 100%). To a solution of 411 (182 mg, 0.64 mmol) in EtOH (2 ml) and toluene (6 ml) was added 2-phenylacetyl isothiocyanate (227 mg, 2 eq, 1.28 mmol) and the reaction mixture was stirred at RT for 2 hrs, concentrated under reduced pressure and the residue was purified by column chromatography (1:3 EtOAc:hexane) to afford 406 as a white solid (25 mg, 9% yield). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 12.49 (s, 1H), 11.82 (s, 1H), 8.58 (d, J=5.48 Hz, 1H), 8.01 (m, 1H), 7.88 (s, 1H), 7.50 (m, 2H), 7.25 (m, 5H), 6.73 (d, J=5.48 Hz, 1H), 5.01 (s, 1H), 3.81 (s, 2H). LCMS: 462.2 (M+H).

Provenance & Evidence