hydrogen; potassium acetate; palladium dichloride in isopropyl alcohol P=3000.2 Torr; 5 h;

1: 5-bromo-2-methoxy-3,6-dimethylpyridine With n-butyllithium in tetrahydrofuran; hexane T=-78°C; 2.5 h; 2: methyl iodide in tetrahydrofuran; hexane T=-78 - 20°C; 0.833333 h; 3: With hydrogenchloride in 1,4-dioxane T=100°C; 1.5 h; Microwave irradiation;

1: 66 percent / phosphorus pentachloride / 1 h / 100 °C 2: 73 percent / palladium dichloride, potassium acetate, hydrogen / propan-2-ol / 5 h / 3000.2 Torr View Scheme

1.1: methanol / 1 h / 100 °C / |Microwave irradiation 2.1: n-butyllithium / tetrahydrofuran; hexane / 2.5 h / -78 °C 2.2: 0.83 h / -78 - 20 °C 2.3: 1.5 h / 100 °C / |Microwave irradiation View Scheme

1.1: TBCA; sulfuric acid / water / 2.5 h / 0 - 20 °C 2.1: methanol / 1 h / 100 °C / |Microwave irradiation 3.1: n-butyllithium / tetrahydrofuran; hexane / 2.5 h / -78 °C 3.2: 0.83 h / -78 - 20 °C 3.3: 1.5 h / 100 °C / |Microwave irradiation View Scheme