4-Methoxybenzylamine → HCID 59631067, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-chloro-7-fluoro-3-methyl-2-(pyridin-2-yl)quinoline (2.0 g, 7.33 mmol), sodium tert-butoxide (1.41 g, 14.67 mmol), tris(dibenzylideneacetone)-dipalladium (0) (0.504 g, 0.550 mmol), XPhos (0.52 g, 1.100 mmol), 4-methoxybenzylamine (0.95 mL, 7.33 mmol), and toluene (15 mL) was stirred at 110° C. under nitrogen for 3 h. Upon completion, the reaction was cooled to 23° C. and concd. The resulting crude residue was taken up in EtOAc, filtered through Celite, and washed with water and brine. The organic phase was dried over magnesium sulfate and concd, affording a crude material that was purified by column chromatography (silica; 0-50% EtOAc in hexanes) to yield 7-fluoro-N-(4-methoxybenzyl)-3-methyl-2-(pyridin-2-yl)quinolin-4-amine as an orange oil. Mass Spectrum (ESI) m/e=374.2 (M+1).

Provenance & Evidence