[NH2:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=[CH:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-].[CH2:24]([O:27][CH2:28][CH2:29]Cl)[CH2:25]Cl>CN(C=O)C.O>[O:27]1[CH2:28][CH2:29][N:1]([C:2]2[CH:3]=[C:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH:5]=[CH:6][CH:7]=2)[CH2:25][CH2:24]1
To a suspension of tert-butyl (3-aminophenyl)carbamate (7.59 g, 36.40 mmol), K2CO3 (10.06 g, 72.80 mmol) and NaI (16.37 g, 109.20 mmol) in DMF (300 mL) was added 2,2′-dichlorodiethyl ether (5.73 g, 40.1 mmol) slowly at 150° C. under N2. The reaction mixture was stirred at 150° C. overnight, then cooled to rt, poured into water (700 mL) and extracted with CH2Cl2 (200 mL×3). The combined organic phases were washed with water (200 mL×3) 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 (5.91 g, 58%).
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