Multi-step reaction with 9 steps
1: H2 / 10percent Pd/C / methanol
2: 100 percent / Na / 4 h / 100 °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
With
2-chloro-1-methyl-pyridinium iodide; hydrogen; sodium; acetic acid; triethylamine;
palladium on activated charcoal;
In
1,4-dioxane; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm00133a008