[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=2[C:11]([OH:13])=O)=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:42][C:43]1[CH:48]=[CH:47][C:46]([OH:49])=[CH:45][CH:44]=1.C(N(C(C)C)C(C)C)C.C(Cl)Cl>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]2[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=2[C:11]([NH:42][C:43]2[CH:48]=[CH:47][C:46]([OH:49])=[CH:45][CH:44]=2)=[O:13])=[CH:6][CH:7]=1In a 100-mL RBF was combined 2-(4-fluorophenylamino)benzoic acid (2.5 g, 11 mmol), HATU (4.9 g, 13 mmol), 4-aminophenol (1.0 g, 9.2 mmol), N-ethyl-N-isopropylpropan-2-amine (3.2 mL, 18 mmol), and DCM (23 mL, 9.2 mmol). The reaction mixture was allowed to stir at RT overnight and was then absorbed onto a loading cartridge and passed through an 80 g silica gel column using hexanes: EtOAc as eluent. Fractions containing pure product were concentrated in vacuo to afford 2-(4-fluorophenylamino)-N-(4-hydroxyphenyl)benzamide as a brown oil. The oil was triturated with CH2Cl2 and hexanes, and the resulting solid was filtered through a 0.45 μM membrane filter and rinsed with hexanes. 2-(4-fluorophenylamino)-N-(4-hydroxyphenyl)benzamide was isolated as a off-white solid. Calcd for C19H15FN2O2: [M]+=322. Found: [M+H]+=323.
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