sulfuric acid in acetonitrile Fischer indole reaction; 24 h; Heating;

1: 54 percent / tri-2-furylphosphine; CuI; Pd2(dba)3 / Bu4NCl / dimethylformamide / 2 h / 20 °C 2: TBAF; AcOH / tetrahydrofuran / 5 h / 20 °C 3: IBX / ethyl acetate / 2 h / 80 °C 4: 28.4 mg / 2-methyl-2-butene; NaH2PO4*H2O; NaClO2 / 2-methyl-propan-2-ol; tetrahydrofuran; H2O / 0.5 h / 20 °C View Scheme

1: 81 percent / pyridine / 1 h / 80 °C 2: 54 percent / tri-2-furylphosphine; CuI; Pd2(dba)3 / Bu4NCl / dimethylformamide / 2 h / 20 °C 3: TBAF; AcOH / tetrahydrofuran / 5 h / 20 °C 4: IBX / ethyl acetate / 2 h / 80 °C 5: 28.4 mg / 2-methyl-2-butene; NaH2PO4*H2O; NaClO2 / 2-methyl-propan-2-ol; tetrahydrofuran; H2O / 0.5 h / 20 °C View Scheme

formic acid in acetic acid 6 h; Heating;

1: TBAF; AcOH / tetrahydrofuran / 5 h / 20 °C 2: IBX / ethyl acetate / 2 h / 80 °C 3: 28.4 mg / 2-methyl-2-butene; NaH2PO4*H2O; NaClO2 / 2-methyl-propan-2-ol; tetrahydrofuran; H2O / 0.5 h / 20 °C View Scheme

1: IBX / ethyl acetate / 2 h / 80 °C 2: 28.4 mg / 2-methyl-2-butene; NaH2PO4*H2O; NaClO2 / 2-methyl-propan-2-ol; tetrahydrofuran; H2O / 0.5 h / 20 °C View Scheme

1.1: potassium hydroxide / ethanol / 12 h / 80 °C / |Schlenk technique; |Inert atmosphere 2.1: potassium tert-butylate / tetrahydrofuran / 0.33 h / 0 °C / |Schlenk technique; |Inert atmosphere 2.2: 10 h / 0 - 20 °C / |Schlenk technique; |Inert atmosphere 3.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / water; acetone / 12 h / 20 °C / |Schlenk technique 4.1: sodium periodate / water; methanol / 8 h / 20 °C / |Schlenk technique 5.1: sodium dihydrogenphosphate; sodium chlorite / water; tetrahydrofuran; tert-butyl alcohol / 0.5 h / 20 °C / |Schlenk technique View Scheme

1.1: potassium tert-butylate / tetrahydrofuran / 0.33 h / 0 °C / |Schlenk technique; |Inert atmosphere 1.2: 10 h / 0 - 20 °C / |Schlenk technique; |Inert atmosphere 2.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / water; acetone / 12 h / 20 °C / |Schlenk technique 3.1: sodium periodate / water; methanol / 8 h / 20 °C / |Schlenk technique 4.1: sodium dihydrogenphosphate; sodium chlorite / water; tetrahydrofuran; tert-butyl alcohol / 0.5 h / 20 °C / |Schlenk technique View Scheme

1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / water; acetone / 12 h / 20 °C / |Schlenk technique 2: sodium periodate / water; methanol / 8 h / 20 °C / |Schlenk technique 3: sodium dihydrogenphosphate; sodium chlorite / water; tetrahydrofuran; tert-butyl alcohol / 0.5 h / 20 °C / |Schlenk technique View Scheme

1.1: sodium iodide; indium / N,N-dimethyl-formamide / 0.25 h / 20 °C / |Schlenk technique; |Inert atmosphere 1.2: 12 h / 100 °C / |Schlenk technique; |Inert atmosphere 2.1: potassium hydroxide / ethanol / 12 h / 80 °C / |Schlenk technique; |Inert atmosphere 3.1: potassium tert-butylate / tetrahydrofuran / 0.33 h / 0 °C / |Schlenk technique; |Inert atmosphere 3.2: 10 h / 0 - 20 °C / |Schlenk technique; |Inert atmosphere 4.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / water; acetone / 12 h / 20 °C / |Schlenk technique 5.1: sodium periodate / water; methanol / 8 h / 20 °C / |Schlenk technique 6.1: sodium dihydrogenphosphate; sodium chlorite / water; tetrahydrofuran; tert-butyl alcohol / 0.5 h / 20 °C / |Schlenk technique View Scheme