m-Chloroperbenzoic acid → Methyl 2-{[2-(4-fluorophenyl)-1-oxidoquinolin-6-yl]sulfonyl}benzoate

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Reaction Steps

3-Chloroperoxybenzoic acid (77%; 82 mg, 0.37 mmol) was added to a solution of methyl 2-{[2-(4-fluorophenyl)quinolin-6-yl]sulfonyl}benzoate [Example 30] (103 mg, 0.24 mmol) in dichloromethane (10 mL). The resulting mixture was stirred at room temperature under nitrogen for 2 days. Calcium hydroxide (308 mg, 4.16 mmol) was added and the resulting slurry stirred for 2 hours. The mixture was filtered and the filter cake washed thoroughly with dichloromethane. The filtrate was evaporated and the residue purified by flash chromatography, eluting with 10-25% diethyl ether/dichloromethane, followed by trituration with diethyl ether to give the title compound as a pale yellow solid (45 mg, 42%). 1H NMR (500 MHz, CDCl3) δ 8.94 (1H, d, J 9.2 Hz), 8.60 (1H, s), 8.28 (1H, m), 8.19 (1H, dd, J 1.6, 9.2 Hz), 8.02 (2H, dd, J 5.4, 8.7 Hz), 7.87 (1H, d, J 8.7 Hz), 7.71-7.61 (4H, m), 7.22 (2H, t, J 8.6 Hz), 3.95 (3H, s); m/z (ES+) 438 [MH+].

Provenance & Evidence