1: 3-bromo-5-(4,5-dihydro-4,4-dimethyloxazol-2-yl)pyridine With lithium diisopropyl amide in tetrahydrofuran T=-78°C; 2: With zinc(II) chloride in tetrahydrofuran; diethyl ether T=-78 - 20°C; 1 h; 3: iodobenzene With tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran; diethyl ether Negishi coupling; 20 h; Heating;

1.1: 70 percent / thionyl chloride / 16 h / 20 °C 2.1: lithium diisopropylamide / tetrahydrofuran / -78 °C 2.2: ZnCl2 / tetrahydrofuran; diethyl ether / 1 h / -78 - 20 °C 2.3: 90 percent / Pd(PPh3)4 / tetrahydrofuran; diethyl ether / 20 h / Heating View Scheme

1.1: CH2Cl2 / 48 h / 0 - 20 °C 2.1: 70 percent / thionyl chloride / 16 h / 20 °C 3.1: lithium diisopropylamide / tetrahydrofuran / -78 °C 3.2: ZnCl2 / tetrahydrofuran; diethyl ether / 1 h / -78 - 20 °C 3.3: 90 percent / Pd(PPh3)4 / tetrahydrofuran; diethyl ether / 20 h / Heating View Scheme

1.1: thionyl chloride / 2 h / Heating 2.1: CH2Cl2 / 48 h / 0 - 20 °C 3.1: 70 percent / thionyl chloride / 16 h / 20 °C 4.1: lithium diisopropylamide / tetrahydrofuran / -78 °C 4.2: ZnCl2 / tetrahydrofuran; diethyl ether / 1 h / -78 - 20 °C 4.3: 90 percent / Pd(PPh3)4 / tetrahydrofuran; diethyl ether / 20 h / Heating View Scheme