1: 2-bromo-5-benzyloxypyridine With n-butyllithium in hexane; toluene T=-78°C; 0.95 h; 2: N,N-dimethyl-formamide in hexane; toluene T=-78°C; 1 h; 3: With water in hexane; toluene T=-10 - 20°C; 2 h;

pyridine in diethyl ether; dichloromethane

1: 85 percent / potassium carbonate / methanol / 0 - 20 °C 2: 95 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 20 °C View Scheme

1: 91 percent / NaH / dimethylformamide; various solvent(s) / 0 °C 2: m-chloroperbenzoic acid / CHCl3 / 0 - 20 °C 3: 95 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 20 °C View Scheme

1: 82 percent / NaH / tetrahydrofuran; dimethylformamide / 20 °C 2: 96 percent / meta-chloroperoxybenzoic acid / CHCl3 / 1 h / cooling 3: 77 percent / 0.5 h / 130 °C 4: 75 percent / NaOH / ethanol; H2O / 1.5 h / Heating 5: 77 percent / MnO2 / CHCl3 / 0.08 h / Heating View Scheme

1.1: potassium carbonate / N,N-dimethyl-formamide / 13 h / 20 °C / Cooling with ice 2.1: n-butyllithium / toluene; hexane / 0.95 h / -78 °C 2.2: 1 h / -78 °C 2.3: 2 h / -10 - 20 °C View Scheme

sodium chlorite; aminosulfonic acid; water in acetone T=0 - 20°C; 6 h;

1: 84 percent / N,N,N',N'-tetramethylguanidine / tetrahydrofuran 2: 49 percent / urea-H2O2 complex; TFAA / acetonitrile 3: H2 / (R,R)-[Rh(Et-DUPHOS)COD(COD)]BF4 / methanol / 48 °C / 2327.23 Torr 4: 92 percent / Zn; aq. NH4Cl / tetrahydrofuran / 20 °C 5: LiOH / tetrahydrofuran; H2O 6: H2; aq. HCl / Pd/C / methanol View Scheme