1: 6-bromobenzo[b]thiophene With n-butyllithium; N,N,N',N,-tetramethylethylenediamine; diisopropylamine in tetrahydrofuran T=-78 - 0°C; 1 h; 2: methyl iodide in tetrahydrofuran; tert-butyl methyl ether T=-78 - 20°C;

1: LAB / tetrahydrofuran; hexane / 0.08 h 2: triethylamine / dichloromethane / 16 h / 20 °C / |Inert atmosphere 3: lithium triethylborohydride / tetrahydrofuran; hexane / 5 h / 0 - 20 °C View Scheme

1: triethylamine / dimethyl sulfoxide / 2 h / 80 - 90 °C 2: LAB / tetrahydrofuran; hexane / 0.08 h 3: triethylamine / dichloromethane / 16 h / 20 °C / |Inert atmosphere 4: lithium triethylborohydride / tetrahydrofuran; hexane / 5 h / 0 - 20 °C View Scheme

1: triethylamine / dichloromethane / 16 h / 20 °C / |Inert atmosphere 2: lithium triethylborohydride / tetrahydrofuran; hexane / 5 h / 0 - 20 °C View Scheme