2-Chloro-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → HCID 137231116, compound

Participants

Reaction Steps

Following general procedure II, 1-(6-chloro-4-{6-[3-(dimethylamino)pyrrolidin-1-yl]pyridin-3-ylamino}-1,5-naphthyridin-3-yl)ethanone (55 mg, 0.134 mmol) was reacted with 2-chloro-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (55 mg, 0.20 mmol) followed by formation of the trihydrochloride salt to afford the desired product (85 mg, 99%) as a yellow solid: 1H NMR (300 MHz, CD3OD) δ 9.41 (s, 1H), 8.54-8.37 (m, 2H), 8.29 (d, J=2.3 Hz, 1H), 7.99 (dd, J=9.5, 2.3 Hz, 1H), 7.39-7.35 (m, 2H), 7.10 (d, J=9.5 Hz, 1H), 4.29-4.11 (m, 2H), 4.03-3.85 (m, 2H), 3.75-3.71 (m, 1H), 3.03 (s, 6H), 2.85 (s, 3H), 2.71-2.82 (s, 1H); ESI MS m/z 521 [M+H]+; HPLC>99% (AUC), tR=8.90 min.

Provenance & Evidence