Sodium Bicarbonate → 5-(3,4-dimethoxyphenyl)-4-(1H-indol-5-yl)nicotinonitrile

Participants

Reaction Steps

A mixture of 4-chloro-5-(3,4-dimethoxyphenyl)nicotinonitrile (120 mg, 0.44 mmol), indole-5-boronic acid (77 mg, 0.48 mmol), Pd(PPh3)4 (25 mg, 0.022 mmol) and aqueous saturated NaHCO3 (3 mL) in DME (4.0 mL) was heated at reflux for 5 h. The reaction mixture was partitioned between water and EtOAc. The combined organics were dried over Na2SO4 and concentrated to give a brown syrup, which was purified by preparative thin-layer chromatography eluting with 3% MeOH/CH2Cl2 to give 94 mg (61%) of 5-(3,4-dimethoxyphenyl)-4-(1H-indol-5-yl)nicotinonitrile 221 as an off-white solid. MS: 356.2 (M+H); melting range: 215-217° C.

Provenance & Evidence