Sodium Iodide → HCID 86586104, compound

Participants

Reaction Steps

To a mixture of 2-tert-butoxycarbonyloxy-4-[3-(1-tert-butoxycarbonyl-3,4-dimethyl-1H-pyrrol-2-yl)-3-oxo-prop-1-ynyl]-5-fluoro-indole-1-carboxylic acid tert-butyl ester (from Example 47 above) (0.79 g, 1.33 mmol) and sodium iodide (Aldrich, 0.50 g, 3.33 mmol) was slowly added TFA (Aldrich, 15 mL) at room temperature. The reaction mixture was stirred at room temperature for 1.5 hours, and then diluted with ethyl acetate and saturated aqueous sodium bicarbonate solution. After separation, the aqueous layer was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The crude product was triturated with ethyl acetate, filtered, and dried to give 5-fluoro-4-[1-iodo-3-oxo-3-(3,4-dimethyl-1H-pyrrol-2-yl)-propenyl]-1,3-dihydro-indol-2-one as a brown solid which was used in the next step without further purification. (Yield 0.40 g, 71.4%).

Provenance & Evidence