Ammonium Hydroxide → 5-(3,4-dimethoxyphenyl)-4-[(4-methyl-1H-indol-7-yl)amino]nicotinonitrile

Participants

Reaction Steps

A solution of 5-(3,4-dimethoxyphenyl)-4-chloronicotinonitrile (120 mg, 0.44 mmol) and 4-methyl-7-aminoindole (77.8 mg, 0.52 mmol) in ethanol (2.5 mL) was heated at the reflux temperature for 24 h and cooled to room temperature. The reaction mixture was treated with aqueous NH4OH and concentrated in vacuo, and the residue was purified by flash column chromatography (ethyl acetate/CH2Cl2 5% to 25%) to provide a 48 mg (29%) of 5-(3,4-dimethoxyphenyl)-4-[(4-methyl-1H-indol-7-yl)amino]nicotinonitrile 530 as an off white solid. HPLC retention time: 9.0 min.(g); MS: 385.3 (M+H); and HRMS: 385.1659.

Provenance & Evidence