Multi-step reaction with 13 steps
1: 100 percent / H2 / 10percent Pd/C / ethyl acetate / 3 h
2: 90 percent / NaOMe / methanol / 1 h / 0 °C
3: tetrahydrofuran
4: triethylamine / dimethylformamide / Ambient temperature
5: 30percent aqueous acetic acid / methanol / 0.5 h / Ambient temperature
6: 44 percent / chromium trioxide dipyridine complex / CH2Cl2 / 0.5 h / 0 °C
7: 85 percent / tetrahydrofuran; diethyl ether / Ambient temperature
8: 90 percent / triethylamine / dimethylformamide / 6 h
9: 70 percent / lithium diisopropylamide / tetrahydrofuran / -78 °C
10: 4-(N,N-dimethylamino)pyridine / CH2Cl2 / 1.5 h
11: 90 percent / 2.5N HCl / methanol
12: imidazole / dimethylformamide
13: 95 percent / benzene / 8 h / Heating; azeotropic removal of water
With
1H-imidazole; hydrogenchloride; dmap; 2,2'-bipyridine-chromium(VI) oxide; hydrogen; sodium methylate; acetic acid; triethylamine; lithium diisopropyl amide;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; benzene;
DOI:10.1016/S0040-4039(01)81132-1