4-Aminopyridine → 3-(1H-Indol-4-YL)-5-(pyridin-4-ylamino)-phenol

Participants

Reaction Conditions

Reaction Steps

[3-Bromo-5-(4-methoxy-benzyloxy)-phenyl]-pyridin-4-yl-amine. A solution of 4-aminopyridine (71 mg, 0.75 mmol), 1,3-dibromo-5-(4-methoxybenzyloxy)benzene (372.0 mg, 1.0 mmol), XantPhos (56 mg, 0.1 mmol), (dibenzylideneacetone)dipalladium (46 mg, 0.05 mmol), and sodium tert-butoxide (192 mg, 2.0 mmol) in dioxane (3 mL) was flushed with nitrogen and the reaction tube was sealed. The reaction mixture was heated to 110° C. for 16 h. After cooling, the reaction mixture was filtered through a short pad of Celite®, and the filtrate was concentrated. The residue was purified by silica gel column chromatography using 5% MeOH in methylene chloride to give a major fraction as a desired product which crystallized from a mixed solution of MeOH/methylene chloride. The crystals were filtered and washed with methanol to give 115 mg of pure 3-bromo-5-(4-methoxy-benzyloxy)-phenyl]-pyridin-4-yl-amine.

Provenance & Evidence