4-Amino-1-methylpiperidine → N2-(5-Methyl-furan-2-ylmethyl)-N5-(1-methyl-piperidin-4-yl)-quinoline-2,5-diamine

Participants

Reaction Conditions

Reaction Steps

(5-Bromo-quinolin-2-yl)-(5-methyl-furan-2-ylmethyl)-amine (150 mg, 0.47 mmol) was dissolved in 2 mL dioxane. Argon was bubbled through the solution for 2 minutes to remove oxygen. 4-Amino-1-methyl-piperidine (165 mg, 1.45 mmol), sodium tert.-butylate (117 mg, 1.22 mmol), 1,1′-bis(diphenylphosphin)ferrocen (41 mg, 0.074 mmol) and 1,1′-bis(diphenylphosphin)ferrocen-palladium(II)chloride (19 mg, 0.023 mmol) were added. The reaction mixture was stirred in a sealed tube at 120° C. overnight. The solvent was evaporated and the residue purified by flash chromatography on silica gel (dichloromethane/methanol/ammonia 100:0:0->90:10:1 gradient). The title compound was obtained as a brown solid (36 mg, 22%), MS: m/e=351.3 (M+H+).

Provenance & Evidence