6-Chloro-2H-thieno[3,2-e][1,2]thiazin-4(3H)-one 1,1-dioxide → HCID 68182946, compound

Participants

Reaction Steps

6-chloro-2,3-dihydro-4H-thieno[3,2-e][1,2]thiazin-4-one 1,1-dioxide (0.800 g, 3.36 mmol) was dissolved in THF (30 mL) and 2-naphthylmagnesium bromide (0.5 M in THF, 33.6 mL, 16.8 mmol) was added. The solution was stirred at room temperature overnight. Reaction was quenched by addition of MeOH (20 mL) and evaporated. The residue was purified using column chromatography on silica gel (80 g Analogix column, gradient 10% EA in hexane to 40% EA in hexane over 20 minutes) to give the title compound (235 mg, 18%). LCMS (FA) ES−: 364, 366. 1H NMR (400 MHz, DMSO) δ 8.46-8.42 (m, 1H), 7.97-7.89 (m, 4H), 7.55-7.52 (m, 2H), 7.35-7.32 (m, 1H), 6.74 (s, 1H), 6.63 (s, 1H), 3.90-3.84 (m, 1H), 3.69-3.64 (m, 1H).

Provenance & Evidence