(Pyrimidin-5-yl)boronic acid → (S)-N-(4-(Chlorodifluoromethoxy)phenyl)-6-(3-(hydroxymethyl)pyrrolidin-1-yl)-5-(pyrimidin-5-yl)nicotinamide

Participants

Reaction Steps

The title compound was prepared in an analogous fashion to that described in Example 169 using (S)-5-bromo-N-(4-(chlorodifluoromethoxy)phenyl)-6-(3-(hydroxymethyl)pyrrolidin-1-yl)nicotinamide (Stage 174.1) and pyrimidin-5-ylboronic acid to afford a white solid. HPLC (Condition 4) tR=4.93 min, UPLC-MS (Condition 3) tR=0.97 min, m/z=476.3 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.57 (m, J=12.10, 7.80 Hz, 1H) 1.84 (m, J=11.90, 6.10 Hz, 1H) 2.12-2.31 (m, 1H) 2.95 (dd, J=10.56, 7.04 Hz, 1H) 3.08-3.44 (m, 5H) 4.60 (t, J=5.08 Hz, 1H) 7.33 (d, J=8.21 Hz, 2H) 7.84 (d, J=9.38 Hz, 2H) 8.07 (d, J=2.35 Hz, 1H) 8.78 (d, J=2.35 Hz, 1H) 8.88 (s, 2H) 9.17 (s, 1H) 10.16 (s, 1H).

Provenance & Evidence