4-(N,N-dimethlyamino)pyridine; triethylamine in dichloromethane T=20°C; 50 h;

1.1: I2 / tetrahydrofuran / 4 h / -20 °C 1.2: 51 percent / tetrahydrofuran / 1.5 h / Heating 2.1: 88 percent / aq. KOH / 1 h / Heating 3.1: 90 percent / Et3N; DMAP / CH2Cl2 / 50 h / 20 °C View Scheme