2-Chloro-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → [6-(3-Chloro-5-fluoro-4-hydroxyphenyl)-4-{4-[1-(dimethylamino)ethyl]piperidin-1-yl}quinolin-3-yl](cyclopropyl)methanone

Participants

Reaction Steps

Following general procedure F, (6-bromo-4-{4-[1-(dimethylamino)ethyl]piperidin-1-yl}quinolin-3-yl)(cyclopropyl)methanone (39 mg, 0.090 mmol) was reacted with 2-chloro-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (30 mg, 0.108 mmol) to afford the desired product (27 mg, 60%) as a light brown solid: 1H NMR (500 MHz, CD3OD) δ 8.81 (s, 1H), 8.26 (d, J=1.6 Hz, 1H), 8.08-7.99 (m, 2H), 7.57-7.51 (m, 1H), 7.46 (dd, J=11.6, 2.2 Hz, 1H), 3.55 (d, J=11.5 Hz, 2-H), 3.27-3.13 (m, 3H), 2.78 (s, 5H), 2.63-2.51 (m, 1H), 2.02 (s, 1H), 1.95 (d, J=12.8 Hz, 2H), 1.82-1.67 (m, 2H), 1.41-1.19 (m, 8H), 0.90 (s, 1H); ESI MS m/z 496 [C28H31ClFN3O2+H]+; HPLC 98.4% (AUC), tR=10.58 min.

Provenance & Evidence