HCID 59807144, compound → HCID 178452053, compound

Participants

Reaction Steps

A solution of compound 4 (0.6586 g, 1.906 mmol) in dry ethanol (20 mL) was treated with methyl thiophene-2-carbimidothioate hydroiodide (1.087 g, 3.812 mmol) at room temperature and was stirred for 3 hours. The mixture was diluted with saturated sodium bicarbonate solution (50 mL) and was extracted with CH2Cl2 (100 mL). The organic layer was washed with brine (20 mL) and dried (Na2SO4). The concentrated crude product was subject to flash chromatography on silica gel using 2.5-5% MeOH/CH2Cl2, which resulted in a brown foam, compound 5 (0.42 g, 48%). 1H NMR (CDCl3) δ 7.42-7.40 (m, 2H), 7.08-7.05 (t, J=9.0 Hz, 1H), 6.92 (d, J=8.1 Hz, 1H), 6.77-6.73 (m, 2H), 4.13-4.09 (m, 2H), 3.37 (tt, J=7.2, 21.9 Hz, 1H), 2.95-2.71 (m, 6H), 1.87 (d, J=12.9 Hz, 2H), 1.77-1.53 (m, 7H), 1.47 (s, 9H); MS-ESI (m/z, %): 457 (MH+, 14), 455 (M+, 100), 219 (18).

Provenance & Evidence