A mixture of 5-(3-bromophenyl)-4-(1H-indol-5-ylamino)nicotinonitrile 113 (39 mg, 0.1 mmol), (Ph3P)4Pd (2.3 mg, 0.002 mmol) and 2M aq. Na2CO3 (0.1 mL) in DME (2 mL) was degassed by bubbling nitrogen for 5 min., then 3-aminophenylboronic acid (17 mg, 0.11 mmol) was added and the mixture was heated at reflux for 12 h. After cooling to r.t., the mixture was filtered and the filtrate was purified by preparative HPLC to give 5-(3′-aminobiphenyl-3-yl)-4-(1H-indol-5-ylamino)nicotinonitrile 117. MS: 402 (M+H), HPLC retention time: 1.72 min.(a).
