pyridine

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;

caesium carbonate in acetonitrile 24 h; Ambient temperature;

1: 85 percent / Cs2CO3 / acetonitrile / 24 h / Ambient temperature 2: 90 percent / 0.1 N methanolic HCl / 2 h / Ambient temperature View Scheme

1: 85 percent / Cs2CO3 / acetonitrile / 24 h / Ambient temperature 2: 60 percent / tetrabutylammonium fluoride trihydrate (Bu4NF) / tetrahydrofuran / 24 h / Ambient temperature 3: 83 percent / pyridine / 24 h / Ambient temperature 4: 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: 85 percent / Cs2CO3 / acetonitrile / 24 h / Ambient temperature 2: 60 percent / tetrabutylammonium fluoride trihydrate (Bu4NF) / tetrahydrofuran / 24 h / Ambient temperature 3: 83 percent / pyridine / 24 h / Ambient temperature View Scheme