(Diethylamino)sulfur trifluoride → 3-(5-Bromopyridin-2-yl)-3-fluorothietane 1,1-dioxide

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Reaction Conditions

Reaction Steps

To a stirred solution of the product of step 2, Example 18 (0.3 g, 1.097 mmol, 1 eq) in methylene chloride (30 mL) is added diethylaminosulfur trifluoride (0.175 mL, 1.295 mmol, 1.1 eq) at −78° C. Resulting reaction mixture is stirred at −78° C. for 1 hour. The reaction mixture is quenched with aqueous bicarbonate solution (15 mL) and extracted with methylene chloride (3×20 mL). Combined organic layer dried over sodium sulphate and concentrated in vacuo. The crude compound is purified by column chromatography using (100-200 mesh silica). Desired compound is eluted in 10% ethyl acetate/hexane to afford title compound (0.15 g): 1H NMR (400 MHz, DMSO) δ: 4.77-4.86 (m, 2H), 4.94-5.05 (m, 2H), 7.62 (d, 1H, J=8.4 Hz), 8.21-8.24 (dd, 1H, J1=8.44 Hz, J2=2.12 Hz), 8.85 (s, 1H). LC-MS (m/z): [M+H] 281.9.

Provenance & Evidence