Sodium Carbonate → 2-(benzyloxy)-5-(2-fluoropyridin-4-yl)-N-(pyridin-3-yl)benzamide

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Reaction Steps

(2-Fluoro-4-pyridinyl)boronic acid (425 mg, 3.02 mmol), bis(triphenylphosphine)palladium(II) chloride (70.6 mg, 0.10 mmol) and sodium carbonate (1066 mg, 10.06 mmol) as a solution in 2 ml of water was added to a solution of 5-bromo-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide (may be prepared as described in example 2; 771 mg, 2.01 mmol) in 1,2-dimethoxyethane (20 ml). The mixture was heated to reflux for 2 hours. The mixture was diluted with ethyl acetate (50 ml) and water (50 ml). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (2×50 ml). The organics were combined and evaporated. The residue was purified by chromatography on silica eluting with 0-10% methanol/dichloromethane 1% ammonia to yield the title compound as an off-white solid. 500 mg.

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