1: 2-bromo-5-methyl-pyridine With n-butyllithium in diethyl ether; hexane T=-78°C; 0.166667 h; 2: N,N-dimethyl acetamide in diethyl ether; hexane T=-78°C; 2 h;

1: 2-bromo-5-methyl-pyridine With n-butyllithium in hexanes; diethyl ether T=-78 - -40°C; 0.25 h; 2: N,N-dimethyl acetamide in hexanes; diethyl ether T=-78°C; 2 h; 3: With ammonium chloride in hexanes; diethyl ether; water

1: 1) Mg, I2 / 1)Et2O, 0 deg C, 2) Et2O, 30 min, reflux 2: hydrogen / PtO2 / acetic acid / 3102.9 Torr / in a Parr hydrogenator 3: 1) Mg, I2 / 1) Et2O, 0 deg C, 2) Et2O, 30 min, reflux View Scheme

1: hydrogen / PtO2 / acetic acid / 3102.9 Torr / in a Parr hydrogenator 2: 1) Mg, I2 / 1) Et2O, 0 deg C, 2) Et2O, 30 min, reflux View Scheme

n-butyllithium; hydrogen bromide; bromine; sodium nitrite Multistep reaction;

iodine; magnesium 1) Et2O, 0 deg C, 2) Et2O, 30 min, reflux; Yield given. Multistep reaction;