2-Chloro-3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine → (S)-6'-Chloro-5'-fluoro-2-(3-(hydroxymethyl)pyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)-[3,3'-bipyridine]-5-carboxamide

Participants

Reaction Steps

The title compound was prepared in an analogous fashion to that described in Example 53 using (S)-5-bromo-6-(3-(hydroxymethyl)pyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 78.1) and 2-chloro-3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine to afford an off-white solid. HPLC (Condition 4) tR=5.69 min, UPLC-MS (Condition 7) m/z=511.1 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.48-1.65 (m, 1H) 1.84 (m, J=5.90 Hz, 1H) 2.15-2.28 (m, 1H) 2.98 (dd, J=10.95, 7.04 Hz, 1H) 3.11-3.41 (m, 5H) 4.61 (t, J=5.28 Hz, 1H) 7.34 (d, J=9.38 Hz, 2H) 7.83 (d, J=9.38 Hz, 2H) 7.99-8.09 (m, 2H) 8.35 (d, J=1.00 Hz, 1H) 8.76 (d, J=2.35 Hz, 1H) 10.16 (s, 1H).

Provenance & Evidence