2,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → Cyclopropyl(6-(3,5-dichloro-4-hydroxyphenyl)-4-(6-(2-(dimethylamino)ethylamino)pyridin-3-ylamino)quinolin-3-yl)methanone

Participants

Reaction Steps

Following general procedure D, (6-bromo-4-(6-(2-(dimethylamino)ethylamino)pyridine-3-ylamino)quinolin-3-yl)(cyclopropyl)methanone (75 mg, 0.17 mmol) was reacted with 2,6-dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (73 mg, 0.25 mmol) to afford the desired product (24 mg, 26%) as an orange solid: 1H NMR (500 MHz, CD3OD+TFA-d) δ 9.38 (s, 1H), 8.32-8.18 (m, 3H), 8.07 (d, J=9.3 Hz, 1H), 7.86 (dd, J=9.3, 2.6 Hz, 1H), 7.48 (s, 2H), 7.15 (d, J=9.3 Hz, 1H), 3.91 (t, J=6.1 Hz, 2H), 3.49 (t, J=6.1 Hz, 2H), 2.99 (s, 6H), 2.87-2.78 (m, 1H), 1.24-1.18 (m, 4H); ESI MS m/z 536 [C28H27Cl2N5O2+H]+; HPLC 96.5% (AUC), tR=11.28 min.

Provenance & Evidence