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0 °C

Isatin (3.2 g, 0.0218 mol) was dissolved in anhydrous DMF (75 mL) and cooled in an ice-bath under a nitrogen atmosphere. To this cold solution, sodium hydride (0.575 g, 0.0239 mol) was added and the reaction was stirred at 0° C. for 1.5 hours. This solution was then treated with 2-(3-bromophenyl)-1,3-dioxolane (5 g, 1 equivalent) followed by CuI (8.3 g, 2 equivalents). The resulting suspension was heated in an oil-bath under nitrogen at 130–140° C. for 16 hours. It was then cooled to room temperature and diluted with an equal volume of chloroform. This suspension was filtered and the filtrate was concentrated under reduced pressure. A viscous brown oil was recovered which was suspended in xylenes (150 mL) wand evaporated to dryness. The residue was used as such for the next reaction. TLC (5% methanol in chloroform) showed clean conversion; Rf (product)=0.86.

1. temperaturecooled in an ice-bath under a nitrogen atmosphere
2. temperatureThe resulting suspension was heated in an oil-bath under nitrogen at 130–140° C. for 16 hours
3. temperatureIt was then cooled to room temperature
4. filtrationThis suspension was filtered
5. concentrationthe filtrate was concentrated under reduced pressure
6. customA viscous brown oil was recovered which
7. customwand evaporated to dryness
8. customsuch for the next reaction