1: 2-hydroxymethyl-1-methyl-1H-indole With n-butyllithium in tetrahydrofuran; hexane T=-78°C; 0.0333333 h; 2: With methanesulfonyl chloride; lithium bromide in tetrahydrofuran; hexane T=0°C; 0.5 h; 3: NaCH(CO2Me)2 in tetrahydrofuran; hexane T=20°C; 2 h;

sodium hydride; 1,2-bis-(diphenylphosphino)ethane; bis(dibenzylideneacetone)-palladium(0) in N,N-dimethyl-formamide T=80°C; 48 h;

1: malonic acid dimethyl ester With sodium hydride in tetrahydrofuran; hexane; mineral oil T=0°C; Inert atmosphere; 2: C11H13NO3S in tetrahydrofuran; hexane; mineral oil T=20°C; 4 h; Inert atmosphere;

1: 2-hydroxymethyl-1-methyl-1H-indole With n-butyllithium; methanesulfonyl chloride; lithium bromide in tetrahydrofuran Inert atmosphere; 2: sodium salt of dimethylmalonate Inert atmosphere;

1: NaBH4 / methanol / 20 °C 2: DMAP; Et3N / diethyl ether / 20 °C 3: 57 percent / dppe; sodium hydride / Pd(dba)2 / dimethylformamide / 48 h / 80 °C View Scheme

1: DMAP; Et3N / diethyl ether / 20 °C 2: 57 percent / dppe; sodium hydride / Pd(dba)2 / dimethylformamide / 48 h / 80 °C View Scheme