CC(C)(C)OC(=O)N1CCNCC1.FC(F)(F)c1cncc(Br)c1>C1COCCO1.CC(C)(C)[O-].O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Na+].[Pd].[Pd].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>CC(C)(C)OC(=O)N1CCN(c2cncc(C(F)(F)F)c2)CC1A 100 ml round bottom equipped with stir bar was charged with (S)-BINAP (331 mg, 0.53 mmol) and Tris(dibenzylideneacetone)dipalladium(0) (203 mg, 0.22 mmol) dissolved in 1,4-dioxane (10.700 mL). This was degassed and purged with nitrogen and stirred at RT for 10 mins. 3-bromo-5-(trifluoromethyl)pyridine (500 mg, 2.21 mmol) followed by tert-butyl piperazine-1-carboxylate (824 mg, 4.42 mmol) and sodium tert-butoxide (850 mg, 8.85 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 30% ethyl acetate in heptane to provide tert-butyl 4-(5-(trifluoromethyl)pyridin-3-yl)piperazine-1-carboxylate (630 mg, 86 %) as an oil.
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