2,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → 2,6-Dichloro-4-(4-((4-((dimethylamino)methyl)phenyl)amino)-3-(methylsulfonyl)quinolin-6-yl)phenol

Participants

Reaction Steps

Following general procedure D, 6-bromo-N-(4-((dimethylamino)methyl)phenyl)-3-(methylsulfonyl)quinolin-4-amine (43 mg, 0.10 mmol) was reacted with 2,6-dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (53 mg, 0.183 mmol) to afford the desired product (31.7 mg, 61%) as a yellow solid. 1H NMR (500 MHz, MeOD) δ 9.00 (s, 1H), 8.06-7.97 (m, 2H), 7.74 (s, 3H), 7.46-7.38 (m, 2H), 7.21 (d, J=8.0 Hz, 2H), 7.13 (s, 2H), 3.86 (s, 2H), 3.27 (s, 3H), 2.45 (s, 6H). ESI MS m/z 516 [C25H23Cl2N3O2S+H]+; HPLC 94.5% (AUC), tR=11.57 min.

Provenance & Evidence