3-Bromopyridine → tert-butyl (3R)-3-methyl-4-pyridin-3-ylpiperazine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

diacetoxypalladium (9.34 mg, 0.04 mmol) and RuPhos (0.039 g, 0.08 mmol) were suspended in 1,4 dioxane (5 mL), degassed and stirred at 50 °C for 10 minutes. Then (R)-tert-butyl 3-methylpiperazine-1-carboxylate (0.100 g, 0.50 mmol), 3-bromopyridine (0.040 mL, 0.42 mmol) and cesium carbonate (0.203 g, 0.62 mmol) were added and the reaction mixture was stirred at 100 °C for 16 h. LCMS showed only 5% conversion to desired product. This was part of a screen and Ruphos, sodium tert-butoxide in toluene gave far better conversion so this was abandoned.

Provenance & Evidence