反应详情

温度

85 °C

To a solution of (S)-2-((tert-butyldimethylsilyloxy)methyl)pyrrolidine (0.455 g, 2.11 mmol) in toluene (20 mL) were added tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3) (0.039 g, 0.042 mmol) and rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthalene (rac-BINAP) (0.066 g, 0.106 mmol). The solution was purged with Argon and heated to 85° C. for 10 min. After cooling to room temperature, sodium tert-butoxide (0.406 g, 4.22 mmol) and 3,5-dibromopyridine (0.5 g, 2.11 mmol) were added and the reaction mixture was then heated to 85° C. over night. The mixture was poured into sat. NH4Cl (20 mL) and the aqueous layer was extracted with DCM (2×25 mL). Combined organics were washed with brine, dried over Na2SO4, filtered and evaporated to dryness. The residue was purified by silica gel flash chromatography eluting with a 0 to 5% MeOH-DCM gradient to give the title compound (0.412 g, 53%) as a yellow oil. MS: 371.0, 372.9 (M+H+).

1. customThe solution was purged with Argon
2. temperatureAfter cooling to room temperature
3. temperaturethe reaction mixture was then heated to 85° C. over night
4. extractionthe aqueous layer was extracted with DCM (2×25 mL)
5. washCombined organics were washed with brine
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. customevaporated to dryness
9. customThe residue was purified by silica gel flash chromatography
10. washeluting with a 0 to 5% MeOH-DCM gradient