phosphorus oxytribromide T=60 - 120°C;

1: 2,4-dibromoquinoline With n-butyllithium in tetrahydrofuran; diethyl ether T=-78°C; 2: methyl iodide in tetrahydrofuran; diethyl ether T=-78 - 20°C;

lithium in tetrahydrofuran 10 h; ultrasound (38 KHz, 125 watts);

potassium hydroxide; Lindlar's catalyst; hydrazine hydrate

1.1: n-BuLi / tetrahydrofuran; hexane / -78 °C 1.2: tetrahydrofuran; hexane / 0.5 h / -78 °C 2.1: 85 percent / NaBH4; acetic acid / tetrahydrofuran; hexane; methanol / -78 - 20 °C View Scheme

1.1: n-BuLi / tetrahydrofuran; hexane / -78 °C 1.2: tetrahydrofuran; hexane / 0.5 h / -78 °C 2.1: 85 percent / NaBH4; acetic acid / tetrahydrofuran; hexane; methanol / -78 - 20 °C 3.1: triethylamine / CH2Cl2 / 3 h / -30 °C 4.1: 85 percent / NaN3; 18-crown-6 / acetonitrile 5.1: triphenylphosphine / tetrahydrofuran / 2 h 5.2: 95 percent / H2O / tetrahydrofuran View Scheme

palladium diacetate; hydrogen; triphenylphosphine; 2,4,6-trimethyl-pyridine; tributyl-amine in acetonitrile T=120°C; P=22501.8 Torr; 18 h;

1: 2-bromo-4-methylquinoline With n-butyllithium in tetrahydrofuran; hexane T=-78°C; 2: N,N-dimethyl-formamide in tetrahydrofuran; hexane T=-78°C; 0.5 h;