1: ethyl 3-methyl-1H-indole-2-carboxylate With sodium hydride in N,N-dimethyl-formamide T=20°C; Metallation; 1 h; 2: methyl iodide in N,N-dimethyl-formamide T=20°C; Alkylation; 5 h;

1.1: 10 percent HCl / ethanol / 0.25 h / Heating 2.1: NaH / dimethylformamide / 1 h / 20 °C 2.2: 90.4 percent / dimethylformamide / 5 h / 20 °C View Scheme

1.1: NaNO2; 35 percent aq. HCl 1.2: 50 percent aq.KOH / ethanol / 0.5 h / 0 °C 2.1: 10 percent HCl / ethanol / 0.25 h / Heating 3.1: NaH / dimethylformamide / 1 h / 20 °C 3.2: 90.4 percent / dimethylformamide / 5 h / 20 °C View Scheme