5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinonitrile → (S)-5'-Cyano-2-(3-(hydroxymethyl)pyrrolidin-1-yl)-N-(4-((trifluoromethyl)thio)phenyl)-[3,3'-bipyridine]-5-carboxamide

Participants

Reaction Steps

The title compound was prepared in an analogous fashion to that described in Example 151 using (S)-5-bromo-6-(3-(hydroxymethyl)pyrrolidin-1-yl)-N-(4-((trifluoromethyl)thio)phenyl)nicotinamide (Stage 189.1) and 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinonitrile to afford a yellow solid. UPLC-MS (Condition 3) tR=1.09 min, m/z=500.3 [M+H]+, m/z=498.3 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.49-1.69 (m, 1H) 1.77-1.96 (m, 1H) 2.16-2.30 (m, 1H) 2.97 (dd, J=11.00, 7.09 Hz, 1H) 3.10-3.22 (m, 2H) 3.22-3.27 (m, 1H) 3.34-3.45 (m, 2H) 4.60 (br. s, 1H) 7.70 (d, J=8.80 Hz, 2H) 7.87-7.99 (m, 2H) 8.09 (d, J=2.45 Hz, 1H) 8.41 (t, J=2.08 Hz, 1H) 8.80 (d, J=2.45 Hz, 1H) 8.91 (d, J=2.20 Hz, 1H) 9.02 (d, J=1.96 Hz, 1H) 10.27 (s, 1H).

Provenance & Evidence