C([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[C:21]([NH2:22])=[CH:20][C:19]([F:23])=[CH:18][N:17]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.C(N1C=CN=C1)(N1[CH:30]=[CH:29]N=C1)=O.[C:36]([O-:39])([O-])=O.[Cs+].[Cs+].O>COCCOC>[CH2:29]([N:22]1[C:21]2[C:16](=[N:17][CH:18]=[C:19]([F:23])[CH:20]=2)[N:15]([C:12]2[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=2)[C:36]1=[O:39])[CH3:30]A mixture of N2-[4-(benzyloxy)phenyl]-5-fluoropyridine-2,3-diamine (0.85 g) and 1,1′-carbonylbis(1H-imidazole) (0.45 g) in DME (10 mL) was stirred at 100° C. for 4 h, and then Cs2CO3 (0.90 g) and 1,1′-carbonylbis(1H-imidazole) (0.892 g) were added successively. The mixture was stirred at 100° C. for 10 min, treated with water, and extracted with AcOEt. The organic layer was dried over MgSO4 and concentrated in vacuo. The residue was dissolved in DMF (10 mL), and then Cs2CO3 (3.58 g) and iodoethane (1.29 g) were added successively. The mixture was stirred at 100° C. for 2 h, treated with water, and extracted with AcOEt. The organic layer was dried over MgSO4 and concentrated in vacuo. The residue was dissolved in EtOH (30 mL), and Pd/C (1.5 g) was added. Under H2 atmosphere, the mixture was stirred at room temperature for 30 min, filtered and evaporated. The residue was chromatographed on silica gel eluting with AcOEt/Hexane to give the title compound (0.52 g).
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