m-Chloroperbenzoic acid → 6-Bromo-1-tosyl-1H-pyrrolo[3,2-b]pyridine 4-oxide

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Reaction Steps

To a stirred solution of 6-bromo-1-tosyl-1H-pyrrolo[3,2-b]pyridine (6.87 g, 19.56 mmol) in DCM (100 mL) at 0° C. was added 3-chloroperbenzoic acid (77 wt %, 5.26 g, 23.47 mmol). The reaction mixture was stirred at RT until the starting material was completely consumed, as monitored by HPLC. After 8 h, the solution was washed with saturated aqueous NaHCO3 (2×). The organic phase was dried over MgSO4, concentrated in vacuo, and purified by silica gel chromatography (2% to 4% MeOH/DCM) to give the title compound as a white solid (5.66 g, 79%). 1H NMR (500 MHz, CDCl3) δ ppm 8.30 (s, 1H), 8.06 (s, 1H), 7.78 (d, 2H, J=8.0 Hz), 7.65 (d, 1H, J=3.5 Hz), 7.33 (d, 2H, J=8.0 Hz), 7.06 (d, 1H, J=3.5 Hz), 2.41 (s, 3H); ESI-MS m/z [M+H]+ calc'd for C14H11BrN2O3S, 367, 369; found 367, 369.

Provenance & Evidence