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0 °C

5-Methoxyisatin (2 g, 0.0113 mol) in anhydrous DMF (15 mL) was cooled in an ice-bath under a nitrogen atmosphere and treated with sodium hydride (0.54 g, 1.2 equivalents, 60% dispersion in mineral oil). The reaction was stirred at 0° C. for 0.5 hour and then 2-bromoanisole (1.4 mL, 1 equivalent) was added along with copper iodide (4.3 g, 2 equivalents). The reaction was heated in an oil-bath at 140° C. for 16 hours. The reaction was then cooled to room temperature and filtered. The filtrate was evaporated to dryness. The dark brown oily solid was used directly for the next reaction.

1. temperatureThe reaction was heated in an oil-bath at 140° C. for 16 hours
2. temperatureThe reaction was then cooled to room temperature
3. filtrationfiltered
4. customThe filtrate was evaporated to dryness
5. customThe dark brown oily solid was used directly for the next reaction