反应详情

温度

100 °C

A solution of 1-benzyloxycarbonyl-1,2,3,4-tetrahydropyridine (8.69 g) in dimethylsulfoxide (50 mL) was treated with 3-bromopyridine (6.32 g), triethylamine (5.6 mL) and palladium(II) acetate (0.499 g). The reaction mixture was heated to 100° C. for 16 hours, cooled to the room temperature, diluted with water, and extracted with ether. The organic layer was washed with water; the combined organic layers were dried and evaporated to produce the crude product. This material was distilled under reduced pressure and the volatile material distilling at 120° C. (66.7 Pa) was removed. The remaining residue was chromatographed, with hexane:ethyl acetate (1:1) as eluent, to afford the coupled product (0.714 g); NMR (CDCl3): 1.7 (broad s, 2), 2.16 (broad m, 1), 3.5-3.7 (m, 2), 4.9-5.1 (d of m, 2), 5.2 (m, 2), 7.0-7.5 (m, 8), 8.5 (m, 2); MS: m/z=295(M+1).

1. temperaturecooled to the room temperature
2. extractionextracted with ether
3. washThe organic layer was washed with water
4. customthe combined organic layers were dried
5. customevaporated
6. customto produce the crude product
7. distillationThis material was distilled under reduced pressure
8. distillationthe volatile material distilling at 120° C. (66.7 Pa)
9. customwas removed
10. customThe remaining residue was chromatographed, with hexane:ethyl acetate (1:1) as eluent