Sodium Carbonate → 4-[6-Amino-5-(2,6-dichloro-benzyloxy)-pyridin-3-yl]-phenol

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Reaction Steps

A mixture of 5-bromo-3-(2,6-dichloro-benzyloxy)-pyridin-2-ylamine (example I(a), 100 mg, 0.29 mmol), 4-(4,4,5,5-tetramethyl-1,3-2-dioxabordan-2-yl) phenol (86 mg, 0.35 mmol), bis(triphenylphosphine) palladium(II) chloride (8 mg, 0.009 mmol) and sodium carbonate (91 mg, 0.87 mmol) in ethylene glycol dimethyl ether (10 mL) and water (0.5 mL) was heated to reflux under nitrogen for 18 hours. The reaction was cooled to ambient temperature and diluted with ethyl acetate. The mixture was washed with water, brine, dried over Na2SO4, and purified on silica column to afford 4-[6-amino-5-(2,6-dichloro-benzyloxy)-pyridin-3-yl]-phenol as light pine crystals (89 mg, 85% yield).

Provenance & Evidence