Iodine → 1-Iodo-6-methylimidazo[1,5-A]pyridine

Participants

Reaction Steps

In a round-bottomed flask, sodium bicarbonate (215 mg, 2.56 mmol) was suspended in water (0.6 ml) and ethanol (1.2 ml). 6-methyl-imidazo[1,5-a]pyridine (90 mg, 0.68 mmol) was added followed by iodine (242 mg, 0.95 mmol). The dark brown suspension was stirred at room temperature overnight then quenched with 10% Na2S2O3-solution and extracted with EtOAc (2×). The organic layers were washed with water and brine then dried over sodium sulfate, filtered and concentrated. The residue was chromatographed over silica gel with EtOAc/hexanes (gradient 0-30% EtOAc) to provide 99 mg (56%) of 1-iodo-6-methyl-imidazo[1,5-a]pyridine as a light brown solid. 1H NMR (CDCl3, 300 MHz): δ (ppm) 8.11 (s, 1H), 7.73 (s, 1H), 7.24 (d, J=9.4 Hz, 1H), 6.67 (d, J=9.1 Hz, 1H), 2.27 (s, 3H).

Provenance & Evidence