[CH3:1][O:2][C:3](=[O:12])[C:4]1[C:9](Cl)=[CH:8][C:7]([CH3:11])=[N:6][CH:5]=1.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=1[OH:21].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O.[Cu]I.[Cu].C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:12])[C:4]1[C:9]([O:21][C:15]2[CH:16]=[C:17]([Cl:20])[CH:18]=[CH:19][C:14]=2[Cl:13])=[CH:8][C:7]([CH3:11])=[N:6][CH:5]=1
To a solution of 0.53 g (2.855 mmol) 4-chloro-6-methyl-nicotinic acid methyl ester (commercially available, CAS RN 886372-05-0) in 7.5 mL dry N,N-dimethylformamide was added 489 mg (2.998 mmol) 2,5-dichlorophenol, 789 mg (5.711 mmol) potassium carbonate, 54 mg (0.286 mmol) copper(I) iodide and 54 mg (0.857 mmol) copper nanopowder (avg. particle size 100 nm). The reaction mixture was stirred at 120° C. for 3 hours and then poured on 30 mL 1M aqueous hydrochloric acid and 30 mL ethyl acetate. The layers were separated and the aqueous layer was extracted with 30 mL ethyl acetate. The combined organic layers were washed with 30 mL brine, dried over magnesium sulfate, filtered and concentrated under vacuum. The residue was purified by silica gel chromatography using a MPLC system (20 g silica gel column, CombiFlash Companion, Isco Inc.) with a gradient of n-heptane:ethyl acetate (100:0 to 0:100), to give 432 mg (48%) of the compound as a light yellow solid. MS (ESI): m/z=312.019 [M+H]+.
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