[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH:16](O)=[O:17].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:2]([NH:1][CH:16]=[O:17])[CH:7]=1A mixture of 1-amino-5-chloro-2-phenoxybenzene (1.00 g, 4.55 mmol), formic acid (0.34 mL, 9.10 mmol), TBTU (1.46 g, 4.55 mmol), DIEA (2.38 mL, 13.6 mmol) and DCM (20 mL) was stirred at rt for 2 h. The solution was transferred to a separatory funnel, 20 mL of sat. aq. NaHCO3 solution was added and the mixture was extracted DCM. The organics were combined and dried (Na2SO4). Solvent was removed under reduced pressure to give a crude residue which was purified via flash chromatography, eluting with 5% EtOAc in hexanes.
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