[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:6]=1[CH3:12])[CH3:2].I[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1.CC(C)(C(=O)CC(=O)C(C)(C)C)C.C(=O)([O-])[O-].[Cs+].[Cs+]>CN1C(=O)CCC1.CCOC(C)=O.Cl[Cu]>[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8]([O:11][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)=[CH:7][C:6]=1[CH3:12])[CH3:2]A mixture of 4-hydroxy-2-methyl-benzoic acid ethyl ester (400 mg), 2-iodo-pyridine (0.29 mL), CuCl (110 mg), 2,2,6,6-tetramethyl-heptane-3,5-dione (TMHD, 0.087 mL), cesium carbonate (940 mg) in NMP (2 mL) was heated at 120° C. for 20 h. Then the reaction was cooled, diluted with EtOAc, solids were filtered off, filtrate was washed with water, diluted NaCl solution, dried over sodium sulfate, filtered off, concentrated, the residue was column purified to give the desired product (531 mg). LC MS ESI+: 258 (M+1)+.
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