Toluene → HCID 178455458, compound

Participants

Reaction Conditions

Reaction Steps

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+).

Provenance & Evidence