Triethylsilane → HCID 68182982, compound

Participants

Reaction Conditions

Reaction Steps

4-(4-chlorophenyl)-6-pyridin-4-yl-3,4-dihydro-2H-thieno[3,2-e][1,2]thiazin-4-ol 1,1-dioxide (25 mg, 0.064 mmol) was suspended in 1,2-Dichloroethane (1.0 mL) and triethylsilane (0.1016 mL, 0.6363 mmol) and Trifluoromethanesulfonic acid (0.02815 mL, 0.3182 mmol) were added to a pressure tube and the resulting yellowish solution was heated at 90° C. overnight. At that time, LCMS indicated mainly the product of elimination. Mixture was cooled to room temperature, solid NaHCO3 (20 mg) was added, mixture was filtered and the filtrate was absorbed on silica gel (1 g). The material was purified by ISCO using DCM to 10% MeOH in DCM over 10 minutes to afford the title compound (10 mg, 42%). LCMS: (FA) ES+ 375, 377. 1H NMR (400 MHz, d6-DMSO) δ: 8.63 (dd, J=4.60, 1.62 Hz, 2H), 7.79 (dd, J=4.58, 1.63 Hz, 2H), 7.64 (s, 1H), 7.51 (s, 4H), 7.06 (s, 1H).

Provenance & Evidence