[CH2:1]([O:3][C:4]1[C:5]([N+:14]([O-])=O)=[CH:6][C:7]([F:13])=[C:8]([CH:12]=1)[C:9]([OH:11])=[O:10])[CH3:2].CN(C=O)C>C(O)C.[Pd]>[NH2:14][C:5]1[C:4]([O:3][CH2:1][CH3:2])=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[C:7]([F:13])[CH:6]=15-ethoxy-2-fluoro-4-nitrobenzoic acid (Intermediate 172; 1.24 g, 5.40 mmol) was stirred and dissolved in ethanol:DMF (50 mL:5 mL) over 5% Pd/C (125 mg) and hydrogenated at ambient temperature for 4 hours. The catalyst was filtered and washed with ethanol and the solvent evaporated. The resultant material was purified on a silica column, eluting with 0-5% MeOH/DCM. Product containing fractions were combined and evaporated to yield the title compound as a pale brown solid (433 mg, 40%)
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