3-Fluoro-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine → N-(4-(Chlorodifluoromethoxy)phenyl)-2-(ethyl(2-hydroxyethyl)amino)-5'-fluoro-[3,3'-bipyridine]-5-carboxamide

Participants

Reaction Steps

The title compound was prepared in an analogous fashion to that described in Example 169 using 5-bromo-N-(4-(chlorodifluoromethoxy)phenyl)-6-(ethyl(2-hydroxyethyl)amino)nicotinamide (Stage 182.1) and 3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine to afford an off-white foam. HPLC (Condition 4) tR=5.71 min, UPLC-MS (Condition 3) tR=1.11 min, m/z=481.3 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 0.88 (t, J=6.84 Hz, 3H) 3.15 (m, J=7.00 Hz, 2H) 3.32-3.41 (m, 2H) 3.42-3.52 (m, 2H) 4.61 (t, J=5.08 Hz, 1H) 7.33 (d, J=8.60 Hz, 2H) 7.83 (d, J=0.78 Hz, 2H) 7.95 (d, J=1.17 Hz, 1H) 8.06 (d, J=1.00 Hz, 1H) 8.52-8.66 (m, 2H) 8.75 (d, J=2.74 Hz, 1H) 10.25 (s, 1H).

Provenance & Evidence