potassium carbonate in N,N-dimethyl-formamide T=23°C; 3 h;

hydrogen; palladium on activated charcoal in methanol 1.5 h;

hydrogen; triethylamine; palladium on activated charcoal in methanol 20 h; Ambient temperature;

1: 86 percent / HCl / tetrahydrofuran / 3 h / 70 - 80 °C 2: 96 percent / K2CO3 / dimethylformamide / 3 h / 23 °C View Scheme

1: pyridine / toluene / 6 h / Heating 2: 53 percent / 80percent H2SO4 / 0.5 h / 75 °C 3: 94 percent / POCl3 / dimethylformamide / 3 h / 90 °C 4: 77 percent / CAN / H2O; acetonitrile / 0.25 h / 0 °C 5: 1.) conc. HCl, 2.) K2CO3, TDA-1 / 1.) CHCl3, 35 deg C, 8 h; 5 min, RT; 2.) DMF, 25 deg C, 1 h 6: 13 percent / H2 / 10percent palladium on carbon / pyridine; methanol / 20 h View Scheme

1: 1.) conc. HCl, 2.) K2CO3, TDA-1 / 1.) CHCl3, 35 deg C, 8 h; 5 min, RT; 2.) DMF, 25 deg C, 1 h 2: 13 percent / H2 / 10percent palladium on carbon / pyridine; methanol / 20 h View Scheme

1: 77 percent / CAN / H2O; acetonitrile / 0.25 h / 0 °C 2: 1.) conc. HCl, 2.) K2CO3, TDA-1 / 1.) CHCl3, 35 deg C, 8 h; 5 min, RT; 2.) DMF, 25 deg C, 1 h 3: 13 percent / H2 / 10percent palladium on carbon / pyridine; methanol / 20 h View Scheme

1: 53 percent / 80percent H2SO4 / 0.5 h / 75 °C 2: 94 percent / POCl3 / dimethylformamide / 3 h / 90 °C 3: 77 percent / CAN / H2O; acetonitrile / 0.25 h / 0 °C 4: 1.) conc. HCl, 2.) K2CO3, TDA-1 / 1.) CHCl3, 35 deg C, 8 h; 5 min, RT; 2.) DMF, 25 deg C, 1 h 5: 13 percent / H2 / 10percent palladium on carbon / pyridine; methanol / 20 h View Scheme

1: pyridine / toluene / 6 h / Heating 2: 53 percent / 80percent H2SO4 / 0.5 h / 75 °C 3: 94 percent / POCl3 / dimethylformamide / 3 h / 90 °C 4: 77 percent / CAN / H2O; acetonitrile / 0.25 h / 0 °C 5: 1.) conc. HCl, 2.) K2CO3, TDA-1 / 1.) CHCl3, 35 deg C, 8 h; 5 min, RT; 2.) DMF, 25 deg C, 1 h 6: 13 percent / H2 / 10percent palladium on carbon / pyridine; methanol / 20 h View Scheme

1: 83 percent / Br2 / CCl4; CHCl3 / 1 h / Ambient temperature 2: 70 percent / CAN / H2O; acetonitrile / 0.25 h / 0 °C 3: 27.1 percent / CHCl3 / 1 h / 25 °C 4: 41 percent / H2 / 10percent palladium on carbon / methanol / 1.5 h View Scheme