4-(N,N-dimethlyamino)pyridine; triethylamine

hydrogen; Lindlar's catalyst in tetrahydrofuran Catalytic hydrogenation; P=1500.12 Torr;

1: 83 percent / pyridine / 16 h / 70 °C 2: 96 percent / H2 / Pd on CaCO3 / tetrahydrofuran / 1500.12 Torr View Scheme

1: 83 percent / pyridine / 16 h / 70 °C 2: 96 percent / H2 / Pd on CaCO3 / tetrahydrofuran / 1500.12 Torr View Scheme

1: 96 percent / TFA / H2O; CHCl3 / 10 h / 70 °C 2: 84 percent / pyridine / 4 h / Ambient temperature 3: 1.) PPh3, DEAD, 2.) MeI / 1.) benzene, rt, 24 h, 2.) toluene, rt, 30 min, reflux, 24 h 4: 60 percent / H2 / Pd/C / ethanol / 12 h / Ambient temperature View Scheme

1: 1.) NaH 2: 93 percent / n-Bu3SnH, AIBN / toluene / Heating 3: 96 percent / TFA / H2O; CHCl3 / 10 h / 70 °C 4: 84 percent / pyridine / 4 h / Ambient temperature 5: 1.) PPh3, DEAD, 2.) MeI / 1.) benzene, rt, 24 h, 2.) toluene, rt, 30 min, reflux, 24 h 6: 60 percent / H2 / Pd/C / ethanol / 12 h / Ambient temperature View Scheme

1: 84 percent / pyridine / 4 h / Ambient temperature 2: 1.) PPh3, DEAD, 2.) MeI / 1.) benzene, rt, 24 h, 2.) toluene, rt, 30 min, reflux, 24 h 3: 60 percent / H2 / Pd/C / ethanol / 12 h / Ambient temperature View Scheme

1: 98 percent / aq. HCl / 7 h / Ambient temperature 2: 1.) NaH 3: 93 percent / n-Bu3SnH, AIBN / toluene / Heating 4: 96 percent / TFA / H2O; CHCl3 / 10 h / 70 °C 5: 84 percent / pyridine / 4 h / Ambient temperature 6: 1.) PPh3, DEAD, 2.) MeI / 1.) benzene, rt, 24 h, 2.) toluene, rt, 30 min, reflux, 24 h 7: 60 percent / H2 / Pd/C / ethanol / 12 h / Ambient temperature View Scheme

1: 1.) PPh3, DEAD, 2.) MeI / 1.) benzene, rt, 24 h, 2.) toluene, rt, 30 min, reflux, 24 h 2: 60 percent / H2 / Pd/C / ethanol / 12 h / Ambient temperature View Scheme

Multistep reaction;