Multi-step reaction with 12 steps
1: hydrogenchloride; water; acetic acid / 8 h / 120 °C
2: methanol / 15 h / 20 °C
3: hydrogenchloride / ethyl acetate / 3 h / 20 °C
4: oxalyl dichloride; N,N-dimethyl-formamide / tetrahydrofuran / 2 h / 20 °C
5: sodium tetrahydroborate / tetrahydrofuran; 1,2-dimethoxyethane / 2 h / 0 °C
6: pyridine; thionyl chloride / tetrahydrofuran; toluene / 3 h / 20 °C
7: ammonia / tetrahydrofuran; ethanol / 5 h / 140 °C / Sealed tube
8: dmap / tetrahydrofuran / 1 h / 20 °C
9: 1,3-bis-(diphenylphosphino)propane; palladium diacetate; triethylamine / dimethyl sulfoxide / 15 h / 80 °C
10: sodium hydroxide / tetrahydrofuran; methanol / 2 h / 20 °C
11: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide
12: hydrogenchloride / tetrahydrofuran; 1,4-dioxane / 15 h / 20 °C
With
pyridine; hydrogenchloride; dmap; sodium tetrahydroborate; thionyl chloride; oxalyl dichloride; 1,3-bis-(diphenylphosphino)propane; ammonia; water; palladium diacetate; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N,N-dimethyl-formamide; sodium hydroxide;
In
tetrahydrofuran; 1,4-dioxane; methanol; 1,2-dimethoxyethane; ethanol; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.bmc.2011.06.059