2-Fluoro-3-(trifluoromethyl)benzeneboronic acid → 5-amino-N-(5-((2S,5R,6S)-5-amino-6-fluorooxepan-2-yl)-1-methyl-1H-pyrazol-4-yl)-2-(2-fluoro-3-(trifluoromethyl)phenyl)thiazole-4-carboxamide

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Reaction Steps

Following the procedure for Example 101 starting from tert-butyl N-[2-bromo-4-[[5-[(2S,5R,6S)-5-(tert-butoxycarbonylamino)-6-fluoro-oxepan-2-yl]-1-methyl-pyrazol-4-yl]carbamoyl]thiazol-5-yl]carbamate (Intermediate 95), and replacing 3,6-dihydro-2H-pyran-4-boronic acid pinacol ester with (2-fluoro-3-(trifluoromethyl)phenyl)boronic acid gave 156. 1H NMR (400 MHz, DMSO-d6) δ 9.37 (s, 1H), 8.56 (t, J=7.7 Hz, 1H), 7.85 (s, 1H), 7.79 (t, J=7.3 Hz, 1H), 7.57 (s, 2H), 7.49 (t, J=7.9 Hz, 1H), 4.91-4.82 (m, 1H), 4.67-4.49 (m, 1H), 4.42-4.26 (m, 1H), 4.21-4.00 (m, 1H), 3.77 (s, 3H), 2.13-2.01 (m, 1H), 1.90-1.67 (m, 4H). LCMS (ES+) m/z 517 (M+1).

Provenance & Evidence