(1-(tert-butoxycarbonyl)-5-cyano-1H-pyrrol-2-yl)boronic acid → 5-(5-Cyano-1H-pyrrol-2-yl)-6-((3 S,4S)-3,4-dihydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Participants

Reaction Steps

The title compound was prepared in an analogous fashion to that described in Example 29 using 5-bromo-6-((3S,4S)-3,4-dihydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 31.1) and (1-(tert-butoxycarbonyl)-5-cyano-1H-pyrrol-2-yl)boronic acid (Stage 29.1) to afford an off-white solid. UPLC-MS (Condition 3) tR=0.94 min, m/z=474.1 [M+H]+, m/z=472.1 [M−H]−; 1H NMR (400 MHz, DMSO-d6) δ ppm 3.02 (d, J=11.86 Hz, 2H) 3.46 (dd, J=11.86, 3.55 Hz, 2H) 3.89 (br. s, 2H) 5.09 (d, J=2.45 Hz, 2H) 6.29 (d, J=3.67 Hz, 1H) 7.03 (d, J=3.67 Hz, 1H) 7.35 (d, J=8.44 Hz, 2H) 7.82-7.90 (m, 2H) 8.07 (d, J=2.45 Hz, 1H) 8.75 (d, J=2.45 Hz, 1H) 10.18 (s, 1H) 12.65 (br. s, 1H).

Provenance & Evidence