[N+:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([O:14][C:15]2[CH:20]=[CH:19][N:18]=[C:17]([NH2:21])[CH:16]=2)=[CH:6][CH:5]=1)([O-])=O.C(Cl)Cl.C(O)(=O)C.[H][H]>CO.[Pt]>[NH2:1][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([O:14][C:15]2[CH:20]=[CH:19][N:18]=[C:17]([NH2:21])[CH:16]=2)=[CH:6][CH:5]=1A solution of 4-(4-nitronaphthalen-1-yloxy)pyridin-2-amine (2.00 g, 7.11 mmol) in a mixture of methanol (70 mL), DCM (70 mL) and acetic acid (5 mL) was subjected to hydrogenation by passage through a Thales H-cube (1.0 mL min−1, RT, 55 mm 10% Pt/C Cat-Cart, full hydrogen mode) and was then evaporated in vacuo. The residue was taken up into DCM (100 mL), and was washed with sat. NaHCO3 (100 mL) and brine (100 mL) and then dried (MgSO4) and evaporated in vacuo. The crude product was purified by flash column chromatography (SiO2, 80 g, EtOAc in isohexane, 20 to 80%, gradient elution) to afford the title compound, Intermediate E as a brown solid (1.70 g, 85%); Rt 1.04 min (Method 2); m/z 252 (M+H)+ (ES+).
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