Selectfluor → HCID 86656451, compound

Participants

Reaction Steps

1-Chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (1.0 equiv.) was added to a solution of (S)-tert-butyl 1-(6-chloro-1,7-naphthyridin-4-yl)piperidin-3-ylcarbamate (1.0 equiv.) in MeCN (0.14 M). After stirring for 18 hours, Na2CO3(sat.) was added to quench. The solution was partitioned between EtOAc and Na2CO3(sat.) washed further with NaCl(sat.), dried over MgSO4, concentrated and purified by silica gel chromatography (25-50-100% EtOAc/hexanes w/0.1% DIEA eluant) to yield (S)-tert-butyl 1-(6-chloro-3-fluoro-1,7-naphthyridin-4-yl)piperidin-3-ylcarbamate (15%), as well as recovered (S)-tert-butyl 1-(6-chloro-1,7-naphthyridin-4-yl)piperidin-3-ylcarbamate (55%). LCMS (m/z): 381.1/383.0 (MH+); LC Rt=4.20 min.

Provenance & Evidence