1: 1.) aq. NaHCO3, 2.) pyridine / 1.) Et2O, RT, 16 h, 2.) from 8 deg C to 10 deg C, 48 h 2: 85 percent / Cs2CO3 / acetonitrile / 24 h / Ambient temperature View Scheme

1: sodium bicarbonate / diethyl ether; H2O 2: 10 percent / pyridine View Scheme

pyridine; sodium hydrogencarbonate 1.) Et2O, RT, 16 h, 2.) from 8 deg C to 10 deg C, 48 h; Yield given. Multistep reaction. Yields of byproduct given;

1: 1.) aq. NaHCO3, 2.) pyridine / 1.) Et2O, RT, 16 h, 2.) from 8 deg C to 10 deg C, 48 h 2: 85 percent / Cs2CO3 / acetonitrile / 24 h / Ambient temperature 3: 90 percent / 0.1 N methanolic HCl / 2 h / Ambient temperature View Scheme

1: 1.) aq. NaHCO3, 2.) pyridine / 1.) Et2O, RT, 16 h, 2.) from 8 deg C to 10 deg C, 48 h 2: 85 percent / Cs2CO3 / acetonitrile / 24 h / Ambient temperature 3: 60 percent / tetrabutylammonium fluoride trihydrate (Bu4NF) / tetrahydrofuran / 24 h / Ambient temperature 4: 83 percent / pyridine / 24 h / Ambient temperature 5: 1.) N,N'-thiocarbonyldiimidazole, 2.) α,α'-azobis(isobutyronitrile), tributyltin hydride / 1.) toluene, MeCN, 80 deg C, 30 min, 2.) MeCN, 80 deg C, 3 h View Scheme

1: 1.) aq. NaHCO3, 2.) pyridine / 1.) Et2O, RT, 16 h, 2.) from 8 deg C to 10 deg C, 48 h 2: 85 percent / Cs2CO3 / acetonitrile / 24 h / Ambient temperature 3: 60 percent / tetrabutylammonium fluoride trihydrate (Bu4NF) / tetrahydrofuran / 24 h / Ambient temperature 4: 83 percent / pyridine / 24 h / Ambient temperature View Scheme

1: 1.) aq. NaHCO3, 2.) pyridine / 1.) Et2O, RT, 16 h, 2.) from 8 deg C to 10 deg C, 48 h 2: 87 percent / Cs2CO3 / acetonitrile / 6 h / Ambient temperature 3: 73 percent / tetrabutylammonium fluoride trihydrate (Bu4NF) / tetrahydrofuran / 24 h / Ambient temperature View Scheme

1: sodium bicarbonate / H2O; diethyl ether / 16 h / 15 °C 2: 4-dimethylaminopyridone / acetonitrile / 2 h / Ambient temperature 3: α,α'-azobisisobutyronitrile, tributyltin hydride / toluene / 4 h / 70 °C 4: 61 percent / tetrabutylammonium fluoride trihydrate / tetrahydrofuran / 1 h / Ambient temperature 5: 93 percent / pyridine / 24 h / 18 °C 6: pyridine / CH2Cl2 / 2 h / Ambient temperature 7: 60 percent / tributyltin hydride, α,α'-azobisisobutironitrile / toluene / 3 h / 70 °C 8: 1N NaOH / methanol / 5 h / Heating; pH = 9 View Scheme

1: sodium bicarbonate / H2O; diethyl ether / 16 h / 15 °C 2: 4-dimethylaminopyridone / acetonitrile / 2 h / Ambient temperature 3: α,α'-azobisisobutyronitrile, tributyltin hydride / toluene / 4 h / 70 °C 4: 61 percent / tetrabutylammonium fluoride trihydrate / tetrahydrofuran / 1 h / Ambient temperature 5: 93 percent / pyridine / 24 h / 18 °C 6: pyridine / CH2Cl2 / 2 h / Ambient temperature 7: 60 percent / tributyltin hydride, α,α'-azobisisobutironitrile / toluene / 3 h / 70 °C 8: 94 percent / 1N HCl / methanol / 0.5 h / Ambient temperature View Scheme