1-Boc-pyrrole-2-boronic acid, pinacol ester → (R)-N-(4-(Chlorodifluoromethoxy)phenyl)-6-(3-hydroxypyrrolidin-1-yl)-5-(1H-pyrrol-2-yl)nicotinamide

Participants

Reaction Steps

The title compound was prepared in an analogous fashion to that described in Example 6 using (R)-5-bromo-N-(4-(chlorodifluoromethoxy)phenyl)-6-(3-hydroxypyrrolidin-1-yl)nicotinamide (Stage 22.1) and tert-butyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-1-carboxylate to afford a grey solid. UPLC-MS (Condition 3) tR=1.06 min, m/z=449.2 [M+H]+, m/z=447.1 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.64-1.77 (m, 1H) 1.77-1.93 (m, 1H) 2.98 (d, J=12.23 Hz, 1H) 3.21-3.29 (m, 2H) 3.37-3.51 (m, 1H) 4.19 (d, J=2.20 Hz, 1H) 4.81 (d, J=3.42 Hz, 1H) 6.02-6.18 (m, 2H) 6.70-6.88 (m, 1H) 7.32 (d, J=9.05 Hz, 2H) 7.79-7.94 (m, 2H) 8.02 (d, J=2.45 Hz, 1H) 8.70 (d, J=2.45 Hz, 1H) 10.15 (s, 1H) 11.10 (d, J=1.47 Hz, 1H).

Provenance & Evidence