反应详情

温度

99 °C

To a solution of 3-bromo-5-[[1-(tert-butoxycarbonyl)-2(R)-pyrrolidinyl]methoxy]pyridine (118 mg, 0.33 mmol) and 4-[2-(2-phenylethoxy)ethyl]piperidine (77 mg, 0.33 mmol) in anhydrous toluene (2 mL) were added successively sodium tert-butoxide (48 mg, 0.50 mmol, 1.5 equiv.), tris(dibenzylideneacetone)dipalladium(0) (6.1 mg, 6.6 μmol, 0.02 equiv.), and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos; 11.5 mg, 20 μmol, 0.06 equiv.). The mixture was degassed and purged with Ar (3 cycles), then warmed to 98-100° C. for 4 h. After cooling to room temperature, the mixture was diluted with EtOAc, and the solution was washed with brine, dried over Na2SO4, and evaporated. The residue was purified by CC on SiO2 with CH2Cl2/EtOAc 4:1, then 1:1. 3-[[1-(tert-Butoxycarbonyl)-2(S)-pyrrolidinyl]methoxy]-5-[4-[2-(2-phenylethoxy)ethyl]-1-piperidinyl]pyridine (96 mg, 57%) was obtained as a pale-yellow oil.

1. customThe mixture was degassed
2. custompurged with Ar (3 cycles)
3. temperatureAfter cooling to room temperature
4. additionthe mixture was diluted with EtOAc
5. washthe solution was washed with brine
6. dry with materialdried over Na2SO4
7. customevaporated
8. customThe residue was purified by CC on SiO2 with CH2Cl2/EtOAc 4:1