(2,3-Difluorophenyl)boronic acid → N-(5-((2S,5R,6R)-5-amino-6-fluorooxepan-2-yl)-1-methyl-1H-pyrazol-4-yl)-2-(2,3-difluorophenyl)thiazole-4-carboxamide

Participants

Reaction Steps

Following the procedure for Example 101 starting from tert-butyl ((3R,4R,7S)-7-(4-(2-bromothiazole-4-carboxamido)-1-methyl-1H-pyrazol-5-yl)-3-fluorooxepan-4-yl)carbamate (Intermediate 100), and replacing 3,6-dihydro-2H-pyran-4-boronic acid pinacol ester with (2,3-difluorophenyl)boronic acid gave 245. 1H NMR (400 MHz, DMSO-d6) δ 10.04 (s, 1H), 8.59 (s, 1H), 8.15-8.06 (m, 1H), 7.77 (s, 1H), 7.72-7.60 (m, 1H), 7.51-7.41 (m, 1H), 5.12-4.82 (m, 2H), 4.26-4.10 (m, 1H), 4.07-3.93 (m, 1H), 3.78 (s, 3H), 3.44-3.30 (m, 1H), 2.15 (ddd, J=11.7, 6.2, 3.5 Hz, 1H), 1.97-1.79 (m, 2H), 1.69 (d, J=13.1 Hz, 1H). LCMS (ES+) m/z 452 (M+1).

Provenance & Evidence