3-Chloro-4-hydroxyphenylboronic Acid → [6-(3-Chloro-4-hydroxyphenyl)-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 (25 mg, 0.060 mmol) was reacted with 3-chloro-4-hydroxyphenylboronic acid (21 mg, 0.120 mmol) to afford the desired product (16.3 mg, 59%) as an off-white solid: 1H NMR (500 MHz, CD3OD) δ 8.74 (s, 1H), 8.28 (s, 1H), 8.05-7.98 (m, 2H), 7.70 (d, J=2.3 Hz, 1H), 7.53 (dd, J=8.4, 2.3 Hz, 1H), 7.06 (d, J=8.4 Hz, 1H), 3.53 (d, J=12.7 Hz, 2H), 3.21 (t, J=11.5 Hz, 2H), 2.60-2.51 (m, 1H), 2.43 (d, J=6.8 Hz, 2H), 2.35 (s, 6H), 2.00-1.84 (m, 3H), 1.65-1.53 (m, 2H), 1.34-1.28 (m, 2H), 1.28-1.17 (m, 2H); ESI MS m/z 464 [C27H30ClN3O2+H]+; HPLC>99% (AUC), tR=10.38 min.

Provenance & Evidence