Sodium Iodide → Ethyl 1-methyl-3-[(1-methylethyl)thio]-5-(phenylmethoxy)-methoxy-1H-indole-2-carboxylate

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Reaction Conditions

Reaction Steps

A mixture of ethyl 1-methyl-3-[(1-methylethyl)sulfinyl]-5-(phenylmethoxy)-1H-indole-2-carboxylate (0.50 g, 1.3 mmol) and sodium iodide (0.69 g, 4.6 mmol) in 30 mL of tetrahydrofuran is cooled to 0° C. and treated dropwise with trifluoroacetic anhydride (1.0 mL, 1.5 g, 7.1 mmol). The mixture is stirred for 10 minutes, then quenched by pouring into 100 mL of cold 5% aqueous sodium bicarbonate solution. The mixture is extracted with ether, and the combined organic layers are washed with 5% aqueous sodium thiosulfate solution, followed by brine. The organic layer is dried (anhydrous magnesium sulfate) and evaporated to give 0.44 g (92%) of product; mp 94°-96° C.

Provenance & Evidence