2-Chloro-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → HCID 178467115, compound

Participants

Reaction Steps

Following general procedure II, 1-(6-chloro-4-{4-[(4-methylpiperazin-1-yl)methyl]-cyclohexyl amino}-1,5-naphthyridin-3-yl)ethanone (53 mg, 0.13 mmol) was reacted with 2-chloro-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (41 mg, 0.152 mmol) followed by formation of the trihydrochloride salt to afford the desired product (11 mg, 14%) as a yellow solid: 1H NMR (500 MHz, CD3OD) δ 9.14 (s, 1H), 8.45 (d, J=9.0 Hz, 1H), 8.32 (d, J=9.0 Hz, 1H), 8.02 (s, 1H), 7.88 (dd, J=11.4, 2.2 Hz, 1H), 5.75-5.65 (m, 1H), 3.70 (br s, 8H), 3.10 (br s, 2H), 3.01 (s, 3H), 2.75 (s, 3H), 2.46-2.42 (m, 2H), 2.16-2.13 (m, 2H), 2.05-2.02 (m, 1H), 1.73-1.61 (m, 2H), 1.46-1.35 (m, 2H); ESI MS m/z 526 [M+H]+; HPLC>99% (AUC), tR=9.14 min.

Provenance & Evidence