3-Bromopyridine → Tert-butyl 4-(pyridin-3-YL)piperazine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

diacetoxypalladium (0.072 g, 0.32 mmol) and RuPhos (0.301 g, 0.64 mmol) were stirred in 1,4-dioxane (11.36 ml) for 10 mins at 50 °C.tert-butyl piperazine-1-carboxylate (0.6 g, 3.22 mmol), 3-bromopyridine (0.310 ml, 3.22 mmol) and sodium tert-butoxide (0.464 g, 4.83 mmol) were added and the reaction mixture was stirred at 100 °C for 64 h. The reaction mixture was filtered through celite. The crude product was purified by flash silica chromatography, elution gradient 20 to 100% EtOAc in heptane. Pure fractions were evaporated to dryness to afford tert-butyl 4-(pyridin-3-yl)piperazine-1-carboxylate (0.322 g, 38.0 %) as a yellow oil which crystallised on standing. This was then combined with EN06111-39-01.

Provenance & Evidence