Multi-step reaction with 9 steps
1.1: tetrafluoroboric acid; sodium nitrite / ethanol; water / 3 h / 0 °C / Inert atmosphere
1.2: 4 h / 100 °C / Inert atmosphere
2.1: hydrogenchloride / toluene / 2 h / Inert atmosphere; Sealed tube; Heating
3.1: sulfuric acid; nitric acid / 1 h / 20 - 80 °C / Inert atmosphere
4.1: tetrahydrofuran / 2.25 h / Inert atmosphere; Cooling
5.1: N,N-dimethyl-formamide / 1 h / 150 °C / Inert atmosphere; Sealed tube
6.1: sodium hydroxide / ethanol / 18 h / Inert atmosphere; Sealed tube; Heating
6.2: 20 °C / pH 2 / Inert atmosphere; Sealed tube
7.1: 4-methylmorpholine N-oxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran / 20 °C / Inert atmosphere
8.1: aluminum (III) chloride; 1-ethyl-3-methyl-1H-imidazol-3-ium chloride / 48 h / 20 °C / Inert atmosphere
8.2: Inert atmosphere; Cooling with ice
9.1: 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 8 h / 20 °C / Inert atmosphere
With
4-methyl-morpholine; hydrogenchloride; aluminum (III) chloride; tetrafluoroboric acid; sulfuric acid; nitric acid; 4-methylmorpholine N-oxide; 1-ethyl-3-methyl-1H-imidazol-3-ium chloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydroxide; sodium nitrite;
In
tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide; toluene;
4.1: |Bartoli Indole Synthesis;
DOI:10.1021/jm3016377