(6-Bromo-4-{4-[(dimethylamino)methyl]piperidin-1-yl}quinolin-3-yl)(cyclopropyl)methanone → [6-(3-Chloro-4-hydroxy-5-methoxyphenyl)-4-{4-[(dimethylamino)methyl]piperidin-1-yl}quinolin-3-yl](cyclopropyl)methanone

Participants

Reaction Steps

Following general procedure D, (6-bromo-4-{4-[(dimethylamino)methyl]piperidin-1-yl}quinolin-3-yl)(cyclopropyl)methanone (35 mg, 0.084 mmol) was reacted with 2-chloro-6-methoxy-4-(3,3,4,4-tetramethylborolan-1-yl)phenol (42 mg, 0.150 mmol) to afford the desired product (29.1 mg, 70%) as an off-white solid: 1H NMR (500 MHz, CDCl3) δ 8.75 (s, 1H), 8.30 (s, 1H), 8.07-7.99 (m, 2H), 7.31 (d, J=2.0 Hz, 1H), 7.25 (d, J=1.9 Hz, 1H), 4.00 (s, 3H), 3.54 (d, J=12.4 Hz, 2H), 3.22 (t, J=12.2 Hz, 2H), 2.59-2.50 (m, 1H), 2.43 (d, J=6.2 Hz, 2H), 2.35 (s, 6H), 2.01-1.83 (m, 3H), 1.67-1.53 (m, 2H), 1.35-1.27 (m, 2H), 1.27-1.19 (m, 2H); ESI MS m/z 494 [C28H32ClN3O3+H]+; HPLC 98.9% (AUC), tR=10.51 min.

Provenance & Evidence