1: 1.) CCl4, -20 deg C, 20 min; 2.) DMF, 60 deg C, 20 h 2: 38 percent / NaH / dimethylsulfoxide / 15 h / 15 °C 3: 1.) 5percent aq. NaOH; 2.) ACAN, 6M nitric acid / 1.) EtOH, 5 h, room temperature; 2.) dioxane, water, 0 deg C, 1 h View Scheme

1: 67 percent / mCPBA / CH2Cl2 2: 91 percent / Al(O-i-Pr)3 / toluene / 110 °C 3: 98 percent / diethylaniline, pyridine / benzene 4: 84 percent / Pd(PPh3)4; diethylaniline, pyridine / tetrahydrofuran / 4 h 5: 95 percent / p-aminothiophenol, cesium carbonate / dimethylformamide / 1 h / 85 °C 6: 92 percent / Pd(dppp)Cl2, lithium triethylborohydride / tetrahydrofuran / 3 h / 0 °C 7: 78 percent / ceric ammoniumnitrate / acetonitrile; H2O; CH2Cl2 View Scheme

pyridine-2,6-dicarboxylic acid; ammonium cerium(IV) nitrate in water; acetonitrile a.) 20 min, 0 deg C b.) 10 min, RT;