2-Chloro-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → 1-(6-(3-Chloro-5-fluoro-4-hydroxyphenyl)-4-((4-((dimethylamino)methyl)phenyl)amino)quinolin-3-yl)propan-1-one

Participants

Reaction Steps

Following general procedure M, 1-(6-bromo-4-((4-((dimethylamino)methyl)phenyl)amino)quinolin-3-yl)propan-1-one (125 mg, 0.30 mmol) was reacted with 2-chloro-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (91 mg, 0.33 mmol) to afford the desired product (89 mg, 62%) as a yellow solid. 1H NMR (300 MHz, DMSO-d6) δ 11.00 (s, 1H), 9.02 (s, 1H), 8.09-7.88 (m, 3H), 7.35-7.18 (m, 4H), 7.16-7.09 (m, 2H), 3.42 (s, 2H), 3.09 (q, J=7.1 Hz, 2H), 2.14 (s, 6H), 0.98 (t, J=7.1 Hz, 3H). APCI MS m/z 478 [C27H25ClFN3O2+H]+; HPLC>99% (AUC), tR=8.10 min.

Provenance & Evidence