4-(Hydroxymethyl)benzeneboronic acid → HCID 58345064, compound

Participants

Reaction Conditions

Reaction Steps

N-(4-(2-(2-aminopyridin-3-yl)-6-bromo-3H-imidazo[4,5-b]pyridin-3-yl)benzyl)benzamide (62.4 mg, 0.125 mmol), CsCO3 (40.6 mg, 0.125 mmol), Pd(PPh3)4 (14.4 mg, 0.013 mmol) and 4-(hydroxymethyl)phenylboronic acid (33.5 mg, 0.25 mmol) were dissolved in DMF (3 mL). The reaction mixture was heated to 150° C. for 15 min and after cooling to room temperature filtered through a Bakerbond filtration column. The reaction mixture was directly purified by reversed phase HPLC to give the desired product as the mono-TFA salt (21 mg, 25% yield). Mp. 171-174° C.; 400 M Hz 1H NMR (DMSO-d6) δ: 9.15 (t, J=6 Hz, 1H), 8.68-8.64 (m, 1H), 8.5-8.47 (m, 1H), 8.08-8.03 (m, 1H), 7.96-7.9 (m, 3H), 7.77-7.72 (m, 3H), 7.6-7.42 (m, 8H), 4.63-4.53 (m, 4H); LCMS [M+H]: 527.

Provenance & Evidence