[F:1][C:2]1[C:7]([C:8]2[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[C:10]([O:16][CH3:17])[CH:9]=2)=[CH:6][C:5]([CH:18]2[O:22][CH2:21][CH2:20][O:19]2)=[C:4]([N+:23]([O-])=O)[CH:3]=1.[BH4-].[Na+]>[Pd].C(O)C.O.C(OCC)(=O)C>[O:19]1[CH2:20][CH2:21][O:22][CH:18]1[C:5]1[C:4]([NH2:23])=[CH:3][C:2]([F:1])=[C:7]([C:8]2[CH:9]=[C:10]([O:16][CH3:17])[CH:11]=[C:12]([O:14][CH3:15])[CH:13]=2)[CH:6]=1A mixture of 2-(6-fluoro-3′,5′-dimethoxy-4-nitrobiphenyl-3-yl)-1,3-dioxolane (1.8 g, 5.2 mmol), sodium borohydride (587.9 mg, 15.5 mmol) and 10% palladium on carbon (0.2 g) in ethanol/water (33 mL, v/v=10/1) was heated at 90° C. for 1 hour. After that, the mixture was diluted with ethyl acetate (150 mL), and washed by water (50 mL) and brine (50 mL). The organic layer was dried over sodium, filtered and concentrated. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=5/1 to 4/1) to afford the title compound (1.4 g, 88%) as a yellow solid. MS (ES+) C17H18FNO4 requires: 319, found: 320 [M+H]+.
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