2-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → Cyclopropyl(4-{4-[1-(dimethylamino)ethyl]piperidin-1-yl}-6-(4-hydroxy-3-methoxyphenyl)quinolin-3-yl)methanone

Participants

Reaction Steps

Following general procedure F, (6-bromo-4-{4-[1-(dimethylamino)ethyl]piperidin-1-yl}quinolin-3-yl)(cyclopropyl)methanone (42 mg, 0.097 mmol) was reacted with 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (36 mL, 0.146 mmol) to afford the desired product (26 mg, 56%) as a yellow solid: 1H NMR (300 MHz, CD3OD) δ 8.82 (s, 1H), 8.29 (d, J=1.6 Hz, 1H), 8.19-7.97 (m, 2H), 7.31 (d, J=2.1 Hz, 1H), 7.23 (dd, J=8.2, 2.1 Hz, 1H), 6.95 (d, J=8.2 Hz, 1H), 3.98 (s, 3H), 3.61 (t, J=12.8 Hz, 2H), 3.48-3.36 (m, 1H), 3.27-3.17 (m, 2H), 2.98-2.84 (m, 5H), 2.67-2.56 (m, 1H), 2.11-1.73 (m, 5H), 1.40 (d, J=6.8 Hz, 3H), 1.34-1.23 (m, 6H); ESI MS m/z 474 [C29H35N3O3+H]+; HPLC 98.6% (AUC), tR=9.95 min.

Provenance & Evidence