Iodine → 2-Iodo-3,5-dimethoxy-4-(4-methoxy-benzyloxy)-pyridine

Participants

Reaction Steps

To a solution of 3,5-dimethoxy-4-(4-methoxy-benzyloxy)-pyridine (120 mg, 0.436 mmol) in dry THF (3 ml) at −78° C. was added t-butyllithium (0.48 mmol, 1.7 M solution in pentane) and the resulting orange mixture was stirred at low temperature for 10 minutes. A solution of iodine (166 mg, 0.654 mmol) in dry THF (2 ml) was added drop-wise and the reaction allowed to warm to room temperature and stir for 15 minutes, then quenched with 10% Na2S2O3 (aq) and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4 and concentrated onto silica-gel under reduced pressure. The solid residue was purified by flash chromatography (silica-gel, eluted with hexanes:EtOAc, 4:1) to give the product as a tan solid (100 mg, 57%). 1H-NMR (300 MHz, CDCl3) δ 7.83 (s, 1H), 7.33 (d, J=8.6 Hz, 2H), 6.86 (d, J=8.6 Hz, 2H), 5.11 (s, 2H), 3.88 (s, 3H), 3.85 (s, 3H), 3.79 (s, 3H).

Provenance & Evidence