C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[CH:9]=[CH:10][C:11](F)=[N:12][CH:13]=1.[NH2:15][C:16]1[C:21]([C:22]2[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=2)=[CH:20][C:19]([Cl:29])=[CH:18][N:17]=1.O>CS(C)=O>[Cl:29][C:19]1[CH:20]=[C:21]([C:22]2[CH:23]=[CH:24][C:25]([O:28][C:11]3[CH:10]=[CH:9][C:8]([Cl:7])=[CH:13][N:12]=3)=[CH:26][CH:27]=2)[C:16]([NH2:15])=[N:17][CH:18]=1A mixture of potassium carbonate (376 mg), 5-chloro-2-fluoropyridine (215 mg) and 4-(2-amino-5-chloropyridin-3-yl)phenol (300 mg) in DMSO (10 mL) was stirred at 120° C. for 5 hr. The mixture was poured into water and extracted with EtOAc. The organic layer was separated, washed with 1N NaOH aq. and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography (NH silica gel, eluted with EtOAc in hexane) to give the title compound (450 mg) as a pale yellow solid.
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