5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo(2,3-b)pyridine → HCID 178467128, compound

Participants

Reaction Steps

Following general procedure II, 1-(6-chloro-4-{trans-4-[(dimethylamino)methyl]-cyclohexylamino}-1,5-naphthyridin-3-yl)ethanone (60 mg, 0.17 mmol) was reacted with 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (60 mg, 0.25 mmol) followed by formation of the trihydrochloride salt to afford the desired product (7.5 mg, 9%) as an off-white solid: 1H NMR (500 MHz, CD3OD) δ 9.19 (s, 1H), 9.08 (s, 2H), 8.65 (d, J=8.9 Hz, 1H), 8.44 (d, J=8.9 Hz, 1H), 7.72 (d, J=3.7 Hz, 1H), 6.91 (d, J=3.6 Hz, 1H), 5.69-5.59 (m, 1H), 3.18 (d, J=6.8 Hz, 2H), 2.94 (s, 6H), 2.77 (s, 3H), 2.55-2.45 (m, 2H), 2.08-1.98 (m, 3H), 1.76-1.64 (m, 2H), 1.48-1.36 (m, 2H). ESI MS m/z 443 [M+H]+; HPLC>99% (AUC), tR=9.25 min.

Provenance & Evidence