[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13].C([O-])([O-])=O.[K+].[K+].[Na+].[I-].[CH2:25]([O:28][CH2:29][CH2:30]Cl)[CH2:26]Cl>CN(C=O)C.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:30][CH2:29][O:28][CH2:25][CH2:26]2)=[CH:4][C:3]=1[NH:9][C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:15])[CH3:14]
To a mixture of tert-butyl (2-fluoro-5-aminophenyl)carbamate (2.02 g, 8.93 mmol), K2CO3 (2.47 g, 17.86 mmoll) and NaI (4.02 g, 26.79 mmol) in DMF (60 mL) was added 2,2′-dichlorodiethyl ether (1.28 g, 8.93 mmol) slowly at 150° C. under N2. The reaction was heated at 150° C. overnight, then cooled to rt, poured into water (200 mL) and extracted with CH2Cl2 (200 mL×2). The combined organic phases were washed with water (200 mL×2) and brine (200 mL), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=4:1) to give the title compound as a yellow solid (0.93 g, 35%).
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