3-Bromo-5-(trifluoromethyl)pyridine → HCID 178418192, compound

Participants

Reaction Conditions

Reaction Steps

A 50 ml round bottom equipped with stir bar was charged with BINAP (225 mg, 0.36 mmol) and Tris(dibenzylideneacetone)dipalladium(0) (138 mg, 0.15 mmol) dissolved in 1,4-dioxane (7.500 mL). This was degassed and purged with nitrogen and stirred at RT for 10 mins. 3-bromo-5-(trifluoromethyl)pyridine (340 mg, 1.50 mmol) followed by tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (597 mg, 3.01 mmol) and sodium tert-butoxide (578 mg, 6.02 mmol) were added, and the reaction was stirred at 80 °C for 2 hrs. The crude material was loaded on a Snap KP-SIL 100g column and purified on a Biotage Isolera One instrument, eluting with 10% to 35% ethyl acetate in heptane to provide tert-butyl 5-(5-(trifluoromethyl)pyridin-3-yl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (425 mg, 82 %) as an oil.

Provenance & Evidence