Isoamyl Nitrite → 3-Iodo-2-methyl-6-(trifluoromethyl)pyridine

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-amino-2-methyl-6-(trifluoromethyl)pyridine (500 mg, 2.84 mmol), isoamyl nitrite 760 μL, 5.68 mmol) and iodide. (793 mg, 3.12 mmol) in dry CHCl3 (10 mL) was stirred at room temperature for 0.5 h. The mixture was heated at 80° C. under N2 for 4 h. The reaction mixture was quenched with saturated Na2S2O3 then partitioned between CH2Cl2 and water. The organic layer was dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography (Si, 1% EtOAc in hexanes) to afford 3-iodo-2-methyl-6-(trifluoromethyl)pyridine. LCMS calc.=288.0; found=288.0 (M+1)+. 1H NMR (500 MHz, CDCl3) δ 8.25 (d, J=8.0 Hz, 1H); 7.22 (d, J=8.1 Hz, 1H); 2.83 (s, 3H).

Provenance & Evidence