3-Pyridinemethanamine → N2-(2-Methoxy-benzyl)-N5-pyridin-3-ylmethyl-quinoline-2,5-diamine

Participants

Reaction Conditions

Reaction Steps

(5-Bromo-quinolin-2-yl)-(2-methoxy-benzyl)-amine (200 mg, 0.583 mmol) was dissolved in 3 mL dioxane. Argon was bubbled through the solution for 2 minutes to remove oxygen. 3-Picolylamine (127 mg, 1.18 mmol), sodium tert.-butylate (144 mg, 1.50 mmol), 1,1′-bis(diphenylphosphin)ferrocen (50 mg, 0.09 mmol) and 1,1′-bis(diphenylphosphin)ferrocen-palladium(II)chloride (24 mg, 0.03 mmol) were added. The reaction mixture was stirred in a sealed tube at 100° C. for 2.5 h. The solvent was evaporated and the residue purified by flash chromatography on silica gel (dichloromethane/methanol 100:0->90:10 gradient). The title compound was obtained as a light brown solid (183 mg, 85%), MS: m/e=371.1 (M+H+).

Provenance & Evidence