Multi-step reaction with 8 steps
1: imidazole / dimethylformamide / 3 h / 25 °C
2: azidotrimethylsilane, DDQ / CHCl3 / 3 h / 25 °C
3: H2 / 5percent Pd/BaSO4 / ethanol / 5 h / 25 °C / 760 Torr
4: 1.) LiClO4 / 1.) THF, 0 deg C, 10 min, 2.) THF, CH3CN, RT, 3 h
5: imidazole / dimethylformamide / 3 h / 25 °C
6: 67 percent / Et3N / CH2Cl2 / 24 h / Ambient temperature
7: 82 percent / n-Bu4NF / toluene; tetrahydrofuran / 0.08 h / 0 °C
8: 55 percent / Cs2CO3 / dioxane / 1 h / 80 °C
With
1H-imidazole; trimethylsilylazide; tetrabutyl ammonium fluoride; hydrogen; lithium perchlorate; caesium carbonate; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
Pd-BaSO4;
In
tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jm960092w