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Oxidation of C3-substituted indole to 2-oxindole
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To a solution of C3-substituted indole (1.0 eq) and KBr (10 mol%) in t-BuOH/H2O (20/1, 0.1 M) at rt was added oxone (1.2 eq, MW = 307), and was stirred for 1–4 h. The reaction was quenched by addition of aq. sat. Na2SO3 and then diluted with EtOAc. The organic fractions were collected and the aqueous phase was extracted with EtOAc three times. The combined organic franctions were washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give the 2-oxindoles.
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