1: thien-3-yl bromide in diisopropylamine Sonogashira coupling; 0.5 h; Inert atmosphere; 2: trimethylsilylacetylene With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide in diisopropylamine T=60°C; Sonogashira coupling; 8 h; Inert atmosphere;

bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide in diethylamine

bis-triphenylphosphine-palladium(II) chloride 12 h; Heating;

piperidine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide 4 h; Heating;

bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide

potassium carbonate in methanol T=20°C;

1: 1.) DIBAL-H; 2.) NBS 2: 1.) tert-BuLi; 2.) (PhSO2)2S / 1.) ether, -80 deg C; 2.) ether 3: TBAF / tetrahydrofuran; H2O View Scheme