Multi-step reaction with 13 steps
1: 100 percent / NaH / 90 °C / 10 Torr
2: 75 percent / diphenylphosphoryl azide (DPPA), Et3N / acetonitrile / 1.5 h / 50 °C
3: 95 percent / CuCl / 5 h / 60 °C
4: H2 / 10percent Pd/C / dioxane / 12 h
5: Et3N, 2-chloro-1-methylpyridinium iodide / CH2Cl2 / 0.25 h / 0 °C
6: 70 percent / glacial AcOH / dimethylformamide / 1.) 20 deg C, 2 d, 2.) 40 deg C, overnight
7: 100 percent / H2 / 10percent Pd/C / dioxane; ethanol / 4 h / Heating
8: Et3N, 2-chloro-1-methylpyridinium iodide / CH2Cl2 / 0.25 h / 0 °C
9: 85 percent / glacial AcOH / dimethylformamide / 1.) 20 deg C, 48 h, 2.) 40 deg C, 24 h
10: 100 percent / H2 / 30percent Pd/C / dioxane; methanol / 2 h / Heating
11: Et3N, 2-chloro-1-methylpyridinium iodide / CH2Cl2 / 0.5 h / 0 °C
12: Et3N / dimethylformamide / 3 h / Ambient temperature
13: 100 percent / 2 h / Heating
With
diphenylphosphoranyl azide; 2-chloro-1-methyl-pyridinium iodide; hydrogen; sodium hydride; acetic acid; triethylamine; copper(l) chloride;
palladium on activated charcoal;
In
1,4-dioxane; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jm00133a008