potassium carbonate in acetone T=20°C;

1: 3-Methylpyridine / anhydrous xylene / 24 h / |Reflux 2: sodium carbonate; palladium on activated charcoal / ethylene glycol dimethyl ether; water / 1 h / 45 °C 3: toluene-4-sulfonic acid / methanol; tetrahydrofuran / 1 h / 60 °C 4: potassium carbonate / acetone / 20 °C View Scheme

1: pyridinium p-toluenesulfonate / dichloromethane / 4 h / 20 °C 2: pyridinium p-toluenesulfonate / 3 h / 95 °C 3: pyridine; iodine / chloroform / 20 °C 4: toluene-4-sulfonic acid / methanol; tetrahydrofuran / 1 h / 60 °C 5: 3-Methylpyridine / anhydrous xylene / 24 h / |Reflux 6: sodium carbonate; palladium on activated charcoal / ethylene glycol dimethyl ether; water / 1 h / 45 °C 7: toluene-4-sulfonic acid / methanol; tetrahydrofuran / 1 h / 60 °C 8: potassium carbonate / acetone / 20 °C View Scheme

1: pyridinium p-toluenesulfonate / 3 h / 95 °C 2: pyridine; iodine / chloroform / 20 °C 3: toluene-4-sulfonic acid / methanol; tetrahydrofuran / 1 h / 60 °C 4: 3-Methylpyridine / anhydrous xylene / 24 h / |Reflux 5: sodium carbonate; palladium on activated charcoal / ethylene glycol dimethyl ether; water / 1 h / 45 °C 6: toluene-4-sulfonic acid / methanol; tetrahydrofuran / 1 h / 60 °C 7: potassium carbonate / acetone / 20 °C View Scheme

1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C 1.2: 1 h / -78 °C 2.1: sodium carbonate; palladium on activated charcoal / ethylene glycol dimethyl ether; water / 1 h / 45 °C 3.1: toluene-4-sulfonic acid / methanol; tetrahydrofuran / 1 h / 60 °C 4.1: potassium carbonate / acetone / 20 °C View Scheme

1.1: bromine / dichloromethane / 0 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C 2.2: 1 h / -78 °C 3.1: sodium carbonate; palladium on activated charcoal / ethylene glycol dimethyl ether; water / 1 h / 45 °C 4.1: toluene-4-sulfonic acid / methanol; tetrahydrofuran / 1 h / 60 °C 5.1: potassium carbonate / acetone / 20 °C View Scheme

1: sodium carbonate; palladium on activated charcoal / ethylene glycol dimethyl ether; water / 1 h / 45 °C 2: toluene-4-sulfonic acid / methanol; tetrahydrofuran / 1 h / 60 °C 3: potassium carbonate / acetone / 20 °C View Scheme

1: pyridine; iodine / chloroform / 20 °C 2: toluene-4-sulfonic acid / methanol; tetrahydrofuran / 1 h / 60 °C 3: 3-Methylpyridine / anhydrous xylene / 24 h / |Reflux 4: sodium carbonate; palladium on activated charcoal / ethylene glycol dimethyl ether; water / 1 h / 45 °C 5: toluene-4-sulfonic acid / methanol; tetrahydrofuran / 1 h / 60 °C 6: potassium carbonate / acetone / 20 °C View Scheme

1: toluene-4-sulfonic acid / methanol; tetrahydrofuran / 1 h / 60 °C 2: 3-Methylpyridine / anhydrous xylene / 24 h / |Reflux 3: sodium carbonate; palladium on activated charcoal / ethylene glycol dimethyl ether; water / 1 h / 45 °C 4: toluene-4-sulfonic acid / methanol; tetrahydrofuran / 1 h / 60 °C 5: potassium carbonate / acetone / 20 °C View Scheme