[F:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][CH:29]=1)[O:5][CH2:6][C:7]1[CH:16]=[CH:15][C:14]2[C:13](=[O:17])[N:12](CC3C=CC(OC)=CC=3)[CH2:11][CH2:10][C:9]=2[N:8]=1.O.[N+]([O-])([O-])=O.[NH4+].[Ce].S(NN)(C1C=CC(C)=CC=1)(=O)=O>CC#N>[F:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][CH:29]=1)[O:5][CH2:6][C:7]1[CH:16]=[CH:15][C:14]2[C:13](=[O:17])[NH:12][CH2:11][CH2:10][C:9]=2[N:8]=1
2-((3-Fluorophenoxy)methyl)-6-(4-methoxybenzyl)-7,8-dihydro-1,6-naphthyridin-5(6H)-one (300 mg, 0.77 mmol) from above was dissolved in CH3CN (5 mL) and water (2 mL) added. Cerium ammonium nitrate (419 mg, 0.77 mmol) was added and after 15 min, the reaction was partitioned between EtOAc (10 mL) and brine (10 mL). The organic layers were concentrated and purified by RP-HPLC (0 to 90% CH3CN). Product containing fractions were treated with PS-TsNHNH2 (2 equiv) to give the compound as a solid (74 mg, 76%). 1H NMR (400 MHz, CDCl3) δ 8.38 (1H, d, J=8), 7.56 (1H, d, J=8), 7.27 (1H, dd, J=16, 7.6), 6.77 (1H, dd, J=13.2, 2.0), 6.71 (2H, m), 5.96 (1H, br s), 5.20 (2H, s), 3.67 (2H, t, J=6.2H), 5.96 (1H, br s), 5.20 (2H, s), 3.67 (2H, t, J=6.8 Hz), 3.24 (2H, t, J=6.8 Hz); LC-MS (M+H)=273.2.
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