反应详情

温度

0 °C

To a mixture of sodium-tert-butoxide (0.18 g, 1.87 mmol) in toluene (2 mL) cooled to 0° C. was added tert-butyl 4-(3-(5-bromopyridin-2-yloxy)benzylidene)piperidine-1-carboxylate (0.6 g, 1.34 mmol). The mixture was degassed for 20 min. Palladium acetate (0.02 g, 0.089 mmol) and (2-biphenyl)di-tert-butylphosphine (0.06 g, 0.2 mmol) was added and the mixture was degassed for 10 min. Pyrrolidine (0.114 g, 1.6 mmol) was added and the mixture was heated at 85° C. for 15 h. The reaction was cooled and then partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over sodium sulfate and evaporated to dryness. The residue was purified by silica gel column chromatography (5% ethyl acetate/hexane) to give the title compound (0.21 g, 35.8%). 1H NMR (500 MHz, DMSO-d6): δ 7.61 (s, 1H), 7.28 (s, 1H), 6.99 (m, 1H), 6.91 (d, J=7.25 Hz, 1H), 6.83 (m, 3H), 6.31 (s, 1H), 3.48 (m, 2H), 3.38 (m, 2H), 3.28 (m, 4H), 2.44 (m, 2H), 2.29 (m, 2H), 2.04 (m, 4H), 1.47 (s, 9H); m/z (436.2, MH+).

1. customThe mixture was degassed for 20 min
2. customthe mixture was degassed for 10 min
3. temperaturethe mixture was heated at 85° C. for 15 h
4. temperatureThe reaction was cooled
5. custompartitioned between ethyl acetate and water
6. washThe organic layer was washed with brine
7. dry with materialdried over sodium sulfate
8. customevaporated to dryness
9. customThe residue was purified by silica gel column chromatography (5% ethyl acetate/hexane)