potassium tert-butylate in 1-methyl-pyrrolidin-2-one T=50°C;

1: pentan-2-one With allyl(1,3-bis(2,6-diisopropylphenyl)imidazolidin-2-ylidene)palladium(IV) chloride; sodium hexamethyldisilazane in tetrahydrofuran T=20°C; 0.0833333 h; Inert atmosphere; 2: 2-Amino-3-bromopyridine in tetrahydrofuran T=20 - 105°C; 4 h; Inert atmosphere; regioselective reaction;

1: Et3N; CuI / Pd(PPh3)2Cl2 / dimethylformamide / 15 h / 20 °C 2: 62 percent / aq. DBU / methanol / 14 h / 85 °C View Scheme

1: pyridine / tetrahydrofuran / Heating 2: Et3N / CH2Cl2 / 0 °C 3: 99 percent / n-Bu4NI; Et3N / Pd(PPh3)4; CuI / acetonitrile / 20 °C 4: 73 percent / t-BuOK / 1-methyl-pyrrolidin-2-one / 50 °C View Scheme

1: 99 percent / n-Bu4NI; Et3N / Pd(PPh3)4; CuI / acetonitrile / 20 °C 2: 73 percent / t-BuOK / 1-methyl-pyrrolidin-2-one / 50 °C View Scheme