sodium carbonate; potassium iodide in N,N-dimethyl-formamide 22.5 h; Ambient temperature;

1: 1 h / Heating 2: Na2CO3 / butan-1-ol / 1.5 h / Heating 3: 93 percent / 2-hydroxypyridine / xylene / 19 h / Heating 4: lithium aluminum hydride, conc. H2SO4 / tetrahydrofuran / 24 h 5: 71 percent / tetrahydrofuran / 1.) 0 deg C, 10 min, 2.) RT, 1 h 6: 87 percent / H2 / 10percent Pd/C / acetic acid / 6 h / 42 °C / 3102.9 Torr 7: 72 percent / potassium iodide, sodium carbonate / dimethylformamide / 22.5 h / Ambient temperature View Scheme

1: thionyl chloride / toluene / 2 h / Heating 2: 1 h / Heating 3: Na2CO3 / butan-1-ol / 1.5 h / Heating 4: 93 percent / 2-hydroxypyridine / xylene / 19 h / Heating 5: lithium aluminum hydride, conc. H2SO4 / tetrahydrofuran / 24 h 6: 71 percent / tetrahydrofuran / 1.) 0 deg C, 10 min, 2.) RT, 1 h 7: 87 percent / H2 / 10percent Pd/C / acetic acid / 6 h / 42 °C / 3102.9 Torr 8: 72 percent / potassium iodide, sodium carbonate / dimethylformamide / 22.5 h / Ambient temperature View Scheme

1: Na2CO3 / butan-1-ol / 1.5 h / Heating 2: 93 percent / 2-hydroxypyridine / xylene / 19 h / Heating 3: lithium aluminum hydride, conc. H2SO4 / tetrahydrofuran / 24 h 4: 71 percent / tetrahydrofuran / 1.) 0 deg C, 10 min, 2.) RT, 1 h 5: 87 percent / H2 / 10percent Pd/C / acetic acid / 6 h / 42 °C / 3102.9 Torr 6: 72 percent / potassium iodide, sodium carbonate / dimethylformamide / 22.5 h / Ambient temperature View Scheme