1: potassium hydroxide; iodine / N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide / 16 h / 90 °C / Inert atmosphere 3: hydrogen / platinum(IV) oxide / acetic acid / 16 h / Inert atmosphere View Scheme

1: With trichlorophosphate T=10 - 50°C; 2: With sodium hydrogencarbonate in water T=60°C; 0.25 h;

1: potassium carbonate / acetonitrile 2: trifluoroacetic acid; triethylsilane / dichloromethane / 0 - 20 °C 3: water; lithium hydroxide hydrate / tetrahydrofuran / 1 h / 20 °C View Scheme

1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 20 °C / Inert atmosphere 2: trifluoroacetic acid; triethylsilane / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 16 h / 85 °C / Inert atmosphere 4: water; lithium hydroxide hydrate / tetrahydrofuran; methanol / 2 h / 20 °C View Scheme

sodium cyanoborohydride; acetic acid T=20°C;

caesium carbonate in acetonitrile T=20 - 25°C; Large scale; Concentration;

1: 2-methyl-5-fluoro-1H-indole With sodium hydride in N,N-dimethyl-formamide; mineral oil T=20°C; 0.5 h; Inert atmosphere; 2: bromoacetic acid methyl ester in N,N-dimethyl-formamide; mineral oil