反应详情

温度

200 °C

A mixture of 5-bromoisoindoline-1,3-dione (2.5 g, 11.06 mmol) and Pd(Ph3P)4 (1.406 g, 1.217 mmol) in DMF (50 ml) was accurately degassed with nitrogen, then Zn(CN)2 (1.299 g, 11.06 mmol) was added, and the solution, splitted in 5 vials, was heated under microwave irradiation at 200° C. for 1 hour. A 3% aqueous solution of NH4OH (200 ml) was added, and the organic phase was extracted with ethyl acetate (3×150 ml). The combined organic layers were washed with brine (150 ml), dried over sodium sulfate and concentrated to dryness. The crude was purified by silica gel flash chromatography (100% DCM to DCM:MeOH=99:1) to afford 1,3-dioxoisoindoline-5-carbonitrile as (0.522 g, 3.03 mmol, 27.4% yield, MS/ESI+ 172.9 [MH]+).

1. customwas accurately degassed with nitrogen
2. customthe solution, splitted in 5 vials
3. additionA 3% aqueous solution of NH4OH (200 ml) was added
4. extractionthe organic phase was extracted with ethyl acetate (3×150 ml)
5. washThe combined organic layers were washed with brine (150 ml)
6. dry with materialdried over sodium sulfate
7. concentrationconcentrated to dryness
8. customThe crude was purified by silica gel flash chromatography (100% DCM to DCM:MeOH=99:1)