反应详情

温度

60 °C

Dichloromethane (0.1 ml) was added to a suspension of zinc (2 g, 31.7 mmol) in N,N-dimethylformamide (5 ml), and the mixture warmed until gas evolution occurred. tert-Butyl 4-iodo-1-piperidinecarboxylate (EP 1078928) (4.9 g, 15.8 mmol), and hydroquinone (35 mg, 0.32 mmol) in N,N-dimethylformamide (5 ml) was added, and the mixture warmed until an exotherm was evident. 4-Bromopyridine (1 g, 6.33 mmol), tris(dibenzylideneacetone)dipalladium (0) (73 mg, 0.127 mmol) and tri(2-furyl)phosphine (59 mg, 0.25 mmol) in N,N-dimethylformamide (5 ml) were added, and the reaction stirred at 60° C. for 30 minutes. The cooled mixture was partitioned between water (100 ml) and diethyl ether (50 ml), and the layers separated. The aqueous phase was extracted with diethyl ether (2×50 ml), the combined organic solutions washed with brine (50 ml), dried (MgSO4) and evaporated under reduced pressure, to give a brown oil. This was purified by column chromatography on silica gel using ethyl acetate:pentane (50:50) as eluant to afford the title compound as a yellow oil, 1.1 g.

1. temperaturethe mixture warmed until gas evolution
2. temperaturethe mixture warmed until an exotherm
3. customThe cooled mixture was partitioned between water (100 ml) and diethyl ether (50 ml)
4. customthe layers separated
5. extractionThe aqueous phase was extracted with diethyl ether (2×50 ml)
6. washthe combined organic solutions washed with brine (50 ml)
7. dry with materialdried (MgSO4)
8. customevaporated under reduced pressure
9. customto give a brown oil
10. customThis was purified by column chromatography on silica gel