1: With tri-isopropoxy-borane; lithium diisopropyl amide in tetrahydrofuran T=0 - 5°C; Inert atmosphere; 2: With hydrogenchloride in tetrahydrofuran; water

lithium diisopropyl amide in tetrahydrofuran; hexane T=-10 - -5°C; 3.5 h;

1.1: sodium hydride / mineral oil; pentane; N,N-dimethyl-formamide / 2.5 h / 0 - 20 °C / |Inert atmosphere 1.2: 18 h / 0 - 20 °C / |Inert atmosphere 2.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 3.5 h / -10 - -5 °C View Scheme

1: N-((5-bromo-3-methoxy-2H-pyrrol-2-ylidene)methyl)-N-ethylethanamine With palladium diacetate; triphenylphosphine in 1,4-dioxane; toluene Suzuki Coupling; Inert atmosphere; 2: 1-(N-methoxycarbonyl)indole-2-boronic acid With sodium carbonate in 1,4-dioxane; water; toluene T=85°C; 5.5 h; Inert atmosphere;