1: 2-acetyl-6-bromo-pyridine With pyridine; iodine T=115°C; 1 h; 2: 2-methyl-2-propenal With ammonium acetate in N,N-dimethyl-formamide T=90°C; 2 h;

1: 3-Methylpyridine With n-butyllithium; 2-(dimethylamino)-ethanol in hexane T=0°C; 1.5 h; 2: With tributyltin chloride in tetrahydrofuran; hexane T=-78°C; 1 h; 3: 2,6-Dibromopyridine With bis-triphenylphosphine-palladium(II) chloride; triphenylphosphine in xylene Stille coupling reaction; 12 h; Heating;

tetrakis(triphenylphosphine) palladium(0) in toluene 72 h; Heating;

ammonium acetate T=90°C; 2 h;

1.1: NaNO2 / acidic aq. solution 1.2: Br2; HBr 2.1: BuLi / tetrahydrofuran / -78 °C 2.2: 95 percent / tetrahydrofuran 3.1: 65 percent / Pd(PPh3)4 / toluene / Heating View Scheme

1.1: BuLi / tetrahydrofuran / -78 °C 1.2: 95 percent / tetrahydrofuran 2.1: 65 percent / Pd(PPh3)4 / toluene / Heating View Scheme

1: 100 percent / I2 / pyridine / 1 h / heating 2: 68 percent / NH4OAc / 2 h / 90 °C View Scheme

1: nBuLi / diethyl ether 2: I2; pyridine View Scheme

1: 2-acetyl-6-bromo-pyridine With pyridine; iodine 2: 2-methyl-2-propenal; formamide