2,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → HCID 136266783, 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 2,6-dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (58 mg, 0.20 mmol) followed by formation of the trihydrochloride salt to afford the desired product (75 mg, 86%) as an orange solid: 1H NMR (300 MHz, CD3OD) δ 9.41 (s, 1H), 8.55-8.38 (m, 2H), 8.30 (d, J=2.4 Hz, 1H), 7.97 (dd, J=9.5, 2.4 Hz, 1H), 7.54 (s, 2H), 7.05 (d, J=9.5 Hz, 1H), 4.20-4.16 (m, 2H), 4.02-3.86 (m, 2H), 3.80-3.70 (m, 1H), 3.03 (s, 6H), 2.85 (s, 3H), 2.82-2.68 (m, 1H), 2.39-2.52 (m, 1H); ESI MS m/z 537 [M+H]+; HPLC>99% (AUC), tR=9.08 min.

Provenance & Evidence