(2-Fluoro-4-methoxyphenyl)boronic acid → N-(5-((2S,5R,6S)-5-amino-6-fluorooxepan-2-yl)-1-methyl-1H-pyrazol-4-yl)-5-fluoro-6-(2-fluoro-4-methoxyphenyl)picolinamide

Participants

Reaction Steps

Following the procedure for Example 101 starting from tert-butyl ((3S,4R,7S)-7-(4-(6-bromo-5-fluoropicolinamido)-1-methyl-1H-pyrazol-5-yl)-3-fluorooxepan-4-yl)carbamate (Intermediate 103), and replacing 3,6-dihydro-2H-pyran-4-boronic acid pinacol ester with (2-fluoro-4-methoxyphenyl)boronic acid gave 226. 1H NMR (400 MHz, DMSO-d6) δ 10.12 (s, 1H), 8.18 (dd, J=8.6, 3.8 Hz, 1H), 8.03 (dd, J=9.6, 8.6 Hz, 1H), 7.88 (s, 1H), 7.69 (t, J=8.8 Hz, 1H), 7.04-6.95 (m, 2H), 4.83 (dd, J=10.5, 3.7 Hz, 1H), 4.32 (ddt, J=48.7, 6.0, 2.6 Hz, 1H), 4.16-3.89 (m, 2H), 3.86 (s, 3H), 3.77 (s, 3H), 3.20-3.06 (m, 1H), 2.13-2.01 (m, 1H), 1.88-1.74 (m, 1H), 1.73-1.56 (m, 4H). LCMS (ES+) m/z 476 (M+1).

Provenance & Evidence