Multi-step reaction with 12 steps
1.1: sulfuric acid; nitric acid / water / 7 h / 25 - 33 °C / Large scale
2.1: tert.-butylnitrite; sulfuric acid / 9.5 h / 20 - 43 °C / Large scale
3.1: N,N-dimethyl-formamide / 80 - 100 °C / Large scale
4.1: methanol; propanoic acid methyl ester; copper(l) iodide / tetrahydrofuran / 21 h / 30 - 72 °C / Large scale
5.1: 5%-palladium/activated carbon; hydrogen / ethyl acetate / 24 h / 25 - 35 °C / 1275.13 - 1500.15 Torr / Autoclave; Large scale
5.2: 10 - 30 °C / Large scale
6.1: trichlorophosphate / neat (no solvent) / 15 h / 40 - 102 °C / Large scale
7.1: methanol / toluene / 8 h / 45 - 55 °C / Large scale
8.1: Methyl isobutyl carbinol / 76 h / 130 - 145 °C / Large scale
9.1: isopropylmagnesium chloride; pyridine / 2-methyltetrahydrofuran / -25 - -10 °C / Large scale
9.2: 3 h / -25 - -10 °C / Large scale
10.1: N,N,N',N',N-pentamethylguanidine / 1-methyl-pyrrolidin-2-one
11.1: tetrabutoxytitanium / 2-methyltetrahydrofuran / Reflux
12.1: chlorine / dichloromethane / 3 h / -2 - 0 °C / Large scale
With
pyridine; tetrabutoxytitanium; methanol; Methyl isobutyl carbinol; copper(l) iodide; tert.-butylnitrite; propanoic acid methyl ester; sulfuric acid; 5%-palladium/activated carbon; hydrogen; isopropylmagnesium chloride; nitric acid; chlorine; trichlorophosphate; N,N,N',N',N-pentamethylguanidine;
In
tetrahydrofuran; 2-methyltetrahydrofuran; 1-methyl-pyrrolidin-2-one; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene;
2.1: |Sandmeyer Reaction / 3.1: |Leimgruber-Batcho Indole Synthesis / 5.1: |Leimgruber-Batcho Indole Synthesis;
DOI:10.1021/acs.oprd.7b00134