C(=O)([O-])[O-].[Na+].[Na+].[N:7]1[CH:12]=[CH:11][C:10](B(O)O)=[CH:9][CH:8]=1.[CH2:16]([O:18][C:19]1[CH:24]=[CH:23][C:22](I)=[CH:21][CH:20]=1)[CH3:17].O>O1CCOCC1.CO>[CH2:16]([O:18][C:19]1[CH:24]=[CH:23][C:22]([C:10]2[CH:11]=[CH:12][N:7]=[CH:8][CH:9]=2)=[CH:21][CH:20]=1)[CH3:17]
Under inert gas atmosphere 88 mg (0.12 mmol) PdCl2(dppf)xCH2Cl2, 13.6 mL (27.2 mmol) 2N sodium carbonate solution and 1.64 g (13.3 mmol) pyridine-4-boronic acid are added to 3.00 g (12.1 mmol) 1-ethoxy-4-iodo-benzene in 18 mL 1,4-dioxane and 6 mL methanol. The mixture is stirred for 2 d at reflux. After that time, water is added. The precipitate is filtered off, taken up in DCM and extracted with water. The organic layer is dried over sodium sulphate and the solvent is evaporated. The residue is purified by column chromatography (silica gel; gradient DCM:MeOH 100:0->95:5) to yield the desired product which is directly used in the next reaction step.
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