Sodium Carbonate → 1-[2-(4-Hydroxymethyl-phenyl)-ethyl]-4-(5-methyl-pyridin-2-ylmethoxy)-1H-pyridin-2-one

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Reaction Steps

To 300 mg (0.72 mmol) 4-(5-bromo-pyridin-2-ylmethoxy)-1-[2-(4-hydroxymethyl-phenyl)-ethyl]-1H-pyridin-2-one (example 12.1a) is added 25 mg (0.04 mmol) bis(triphenylphosphan)palladium(II)-chloride, 1.08 mL (2.17 mmol) 2 M aqueous Na2CO3-solution and a solution of 65 mg (1.08 mmol) methyl-boronic acid in 10 mL 1,4-dioxane/5 mL MeOH. The reaction mixture is refluxed for 48 h. The solvent is evaporated and the residue is dissolved in water/DCM. The layers are separated and the aqueous phase is extracted with DCM. The combined organic phase is dried over MgSO4, filtered and the solvent is evaporated. The residue is purified via reverse HPLC chromatography (Waters symmetry, C18; water (0.15% formic acid)/acetonitrile 95:5 to 10:90).

Provenance & Evidence