4-(N,N-dimethlyamino)pyridine; triethylamine in dichloromethane T=20°C; 3 h;

pyridine; 4-(N,N-dimethlyamino)pyridine in dichloromethane 6 h; Heating;

1: 72 percent / TMSOTf / HfCl4 2: 89 percent / t-BuOK / dimethylsulfoxide 3: 85 percent / NaH / dimethylformamide 4: 89 percent / BBr3 / CH2Cl2 5: 99 percent / pyridine 6: 86 percent / K2CO3 / methanol 7: 74 percent / NaH / dimethylformamide 8: 100 percent / KF; HBr / dimethylformamide 9: 46 percent / K2CO3 / acetone; H2O 10: 61 percent / MeLi / tetrahydrofuran View Scheme