Multi-step reaction with 14 steps
1: acetic anhydride; hydrogen bromide; acetic acid / toluene / 1.5 h / 105 °C
2: acetic anhydride; acetic acid; sodium acetate; sodium dichromate / toluene / 60 °C
3: potassium hydroxide / toluene; ethanol / 0.5 h / 20 °C
4: pyridinium chlorochromate; silica gel / dichloromethane / 2 h / 20 °C
5: triethylamine / 20 °C
6: Dess-Martin periodane / dichloromethane / 1 h / 20 °C
7: acetic acid; sodium nitrite / dimethyl sulfoxide / 20 °C
8: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C
9: sodium tetrahydroborate; methanol / tetrahydrofuran / 0.5 h / 0 °C
10: sodium hydroxide; water / tetrahydrofuran; methanol / 20 °C
11: triethylamine; dmap / dichloromethane / 1 h / 0 °C
12: trifluoroacetic acid / dichloromethane / 3 h / 20 °C
13: acetic acid; silver benzoate / dichloromethane / 48 h / 20 °C
14: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C
With
methanol; dmap; sodium tetrahydroborate; sodium dichromate; water; hydrogen bromide; sodium acetate; silver benzoate; acetic anhydride; silica gel; Dess-Martin periodane; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; potassium hydroxide; sodium hydroxide; sodium nitrite;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;