ammonia in tetrahydrofuran T=20°C; 0.25 h;

pyridine; acetic anhydride

1: 72 percent / acetic anhydride; pyridine 2: 71 percent / copper(II) oxide; potassium carbonate; potassium fluoride / palladium(II) bromide; 1,10-phenanthroline / quinoline / 24 h / 170 °C 3: 45 percent / N-bromosuccinimide; azobis(isobutyronitrile) / CCl4; cyclohexane / 18 h / 75 °C View Scheme

1.1: 72 percent / acetic anhydride; pyridine 2.1: 50 percent / basic copper(II) carbonate; potassium carbonate; triphenylphosphine / palladium(II) bromide; 1,10-phenanthroline / quinoline / 24 h / 170 °C 3.1: molecular sieves 3 Angstroem / tetrahydrofuran / 60 h / 20 °C 3.2: 90 percent / sodium cyanoborohydride / tetrahydrofuran; ethanol / 24 h / 23 °C View Scheme

1: 72 percent / acetic anhydride; pyridine 2: 50 percent / basic copper(II) carbonate; potassium carbonate; triphenylphosphine / palladium(II) bromide; 1,10-phenanthroline / quinoline / 24 h / 170 °C View Scheme

1.1: 72 percent / acetic anhydride; pyridine 2.1: 50 percent / basic copper(II) carbonate; potassium carbonate; triphenylphosphine / palladium(II) bromide; 1,10-phenanthroline / quinoline / 24 h / 170 °C 3.1: molecular sieves 3 Angstroem / tetrahydrofuran / 60 h / 20 °C 3.2: 90 percent / sodium cyanoborohydride / tetrahydrofuran; ethanol / 24 h / 23 °C 4.1: 98 percent / pyridine / CH2Cl2 / 2 h / 40 °C 5.1: sodium azide; tri-n-butyltin chloride; tetrabutylammonium bromide / toluene / 72 h / Heating 5.2: 55 percent / acetic acid / toluene; H2O 6.1: 99 percent / NaOH / diethyl ether; H2O / 20 °C View Scheme

1: 72 percent / acetic anhydride; pyridine 2: 71 percent / copper(II) oxide; potassium carbonate; potassium fluoride / palladium(II) bromide; 1,10-phenanthroline / quinoline / 24 h / 170 °C View Scheme

1: 72 percent / acetic anhydride; pyridine 2: 71 percent / copper(II) oxide; potassium carbonate; potassium fluoride / palladium(II) bromide; 1,10-phenanthroline / quinoline / 24 h / 170 °C 3: 17 percent / N-bromosuccinimide; azobis(isobutyronitrile) / CCl4; cyclohexane / 18 h / 75 °C View Scheme