1: copper(II) oxide; potassium carbonate; potassium fluoride / palladium(II) bromide; 1,10-phenanthroline / quinoline / 24 h / 170 °C 2: 167.9 mg / aq. HCl / 2 h / 50 °C View Scheme

1: 88 percent / p-toluenesulfonic acid / toluene / 15 h / Heating 2: copper(II) oxide; potassium carbonate; potassium fluoride / palladium(II) bromide; 1,10-phenanthroline / quinoline / 24 h / 170 °C 3: 167.9 mg / aq. HCl / 2 h / 50 °C View Scheme

potassium carbonate in ethanol; water T=50°C; Suzuki coupling; 20 h;

1: 1.) NaOAc, 2.) 3 N HCl / 1.) DMF 2: 1.) (p-hydroxyphenyloxy)methyl polystyrene, Ph3P, DIAD, NMM, 2.) palladium compound, 3.) aq. CsF View Scheme

4-methyl-morpholine; di-isopropyl azodicarboxylate; (p-hydroxyphenyloxy)methyl polystyrene; palladium compound; triphenylphosphine; cesium fluoride Yield given. Multistep reaction;

hydrogenchloride T=50°C; 2 h;

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.55 h / -100 - -78 °C / |Inert atmosphere 1.2: 1 h / -100 - -78 °C / |Inert atmosphere 2.1: bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 0.05 h / 160 °C / |Microwave irradiation; |Inert atmosphere; |Sealed tube View Scheme

1: With 3 A molecular sieve in tetrahydrofuran T=20°C; 60 h; 2: With sodium cyanoborohydride in tetrahydrofuran; ethanol T=23°C; 24 h; Further stages.;

1.1: molecular sieves 3 Angstroem / tetrahydrofuran / 60 h / 20 °C 1.2: 90 percent / sodium cyanoborohydride / tetrahydrofuran; ethanol / 24 h / 23 °C 2.1: 98 percent / pyridine / CH2Cl2 / 2 h / 40 °C 3.1: sodium azide; tri-n-butyltin chloride; tetrabutylammonium bromide / toluene / 72 h / Heating 3.2: 55 percent / acetic acid / toluene; H2O 4.1: 99 percent / NaOH / diethyl ether; H2O / 20 °C View Scheme