3,5-Dibromopyridine → Tert-butyl 4-(5-bromopyridin-3-yl)piperazine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a suspension of 3,5-dibromopyridine (2 g, 8.44 mmol), 1,1-dimethylethyl 1-piperazinecarboxylate (1.572 g, 8.44 mmol), BINAP (0.210 g, 0.338 mmol) and sodium tert-butoxide (1.136 g, 11.82 mmol) in Toluene (50 mL) at RT, was added Pd2dba3 (0.42 g, 0.459 mmol). The reaction mixture was heated at 100° C. for 3 hours and was cooled to RT, followed by filtration through a short pad of celite (washed with ethyl acetate). The filtrate was concentrated in vacuo to give a residue, which was purified on silica gel, eluting with a gradient of 0-20% ethyl acetate in cyclohexane, to give the title compound (1.8 g). LCMS (A): m/z (M+H)+ 342/344, C14H20BrN3O2 requires 341/343 (acidic).

Provenance & Evidence