[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]([OH:14])=[O:13])[CH:8]=[CH:7]2.[C:15](=O)([O-])[O-].[Cs+].[Cs+].CI>CN(C=O)C.CCOC(C)=O>[CH3:15][O:13][C:12]([C:9]1[CH:8]=[CH:7][C:6]2[C:11](=[C:2]([Br:1])[CH:3]=[N:4][CH:5]=2)[N:10]=1)=[O:14]8-Bromo-[1,6]naphthyridine-2-carboxylic acid methyl ester (2) is prepared by combining compound 1 (1 equiv.), cesium carbonate (1.1 equiv.) and methyl iodide (1.1 equiv.) in DMF (10 mL) and stirring for 16 hrs. at room temperature. The reaction is concentrated in vacuo to give a brown solid, which is dissolved in EtOAc (50 mL) and washed with water (2×50 mL). The EtOAc layer is dried over sodium sulfate, filtered, and concentrated in vacuo to afford a purple solid. The crude product is purified via silica gel chromatography (EtOAc) to yield (2) as a yellow solid, 65%, LC/MS (M+H) 269.0.
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