(4-Methoxyphenyl)boronic acid → 4-amino-8-(4-methoxyphenyl)-N-propyl-cinnoline-3-carboxamide

Participants

Reaction Steps

Using method F, 4-amino-8-iodo-N-propyl-cinnoline-3-carboxamide (178 mg, 0.50 mmol) and 4-methoxyphenylboronic acid (303 mg, 2.00 mmol) were reacted (reflux 14 hours) to afford the title compound (118 mg, 70% yield) as a white solid. 1H NMR (300 MHz, CDCl3) δ8.58 (bm, 1H), 7.69-7.83 (m, 3H), 7.62 (d, J=8.9 Hz, 2H), 7.05 (d, J=8.9 Hz, 2H), 3.87 (s, 3 H), 3.45 (apparent q, J=6.6 Hz, 2H), 1.65 (apparent sextet, J=7.4 Hz, 2H), 1.00 (t, J=7.4 Hz, 3H). MS APCI, m/z=337 (M+H) HPLC 1.71 min.

Provenance & Evidence