Sodium Iodide → 3-(5-Chloro-2-methoxy-phenyl)-3-fluoro-2-oxo-6-trifluoromethyl-2,3-dihydro-indole-1-carboxylic acid iodomethyl ester

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Reaction Steps

To a 25 mL flask containing (S)-3-(5-chloro-2-methoxy-phenyl)-3-fluoro-2-oxo-6-trifluoromethyl-2,3-dihydro-indole-1-carboxylic acid chloromethyl ester ((S)-XII) (0.633 g, 1.40 mmol) was added 6 mL anhydrous acetone, and sodium iodide (0.314 g, 2.10 mmol). The reaction was heated to reflux and stirred for 4 hours, then the reaction was cooled to room temperature, and the solvent was evaporated in vacuo. The crude oil was dissolved in dichloromethane and washed with a 1% aq. sodium thiosulfate solution. The organic layer was separated, dried (Na2SO4) and evaporated in vacuo producing the title compound (0.640 g, 84%) which was used in subsequent reactions without purification. 1H NMR (CDCl3 400 MHz): δ=8.38 (s, 1H), 7.78 (s, 1H), 7.48 (d, 1H, J=7 Hz), 7.36 (d, 1H, J=7 Hz), 7.31 (d, 1H, J=7 Hz), 6.77 (d, 1H, J=7 Hz), 6.28 (d, 1H, J=6.4 Hz), 6.18 (d, 1H, J=6.4 Hz), 3.56 (s, 3H).

Provenance & Evidence