[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:4]=1[C:5]([OH:7])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Br:39][C:40]1[CH:46]=[CH:45][C:43]([NH2:44])=[CH:42][CH:41]=1>C1COCC1>[Br:39][C:40]1[CH:46]=[CH:45][C:43]([NH:44][C:5](=[O:7])[C:4]2[CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=[CH:11][C:3]=2[O:2][CH3:1])=[CH:42][CH:41]=1A mixture of 2-methoxy-5-nitro-benzoic acid (2.00 g, 10.1 mmol), HATU (3.86 g, 10.1 mmol), TEA (4.23 mL) and 100 mL THF was stirred for 30 min. Then 4-bromoaniline (1.75 g, 10.1 mmol) was added and the mixture was stirred for 3 days and concentrated. The crude material was dissolved in EtOAc and the organic phase was washed with satd. aq. NaHCO3. The precipitate was collected and again dissolved in EtOAc and washed with water and satd. NaHCO3. The organic phase was dried with Na2SO4, filtered and concentrated to furnish the subtitle compound. Yield: 930 mg (26%). MS [M+H]+=351 (Br-isotope pattern); TLC: Rf=0.94 (silica gel, DCM:EtOH 9:1).
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