N-Iodosuccinimide → 2-Chloro-4-iodo-3-methylfuro[2,3-c]pyridin-7-amine

Participants

Reaction Steps

2-chloro-3-methylfuro[2,3-c]pyridin-7-amine (1.0 g, 5.5 mmol) in MeCN (30 mL) was treated with N-iodosuccinimide (1.70 g, 7.52 mmol), added portionwise over a 5 min period. The mixture was stirred at RT for overnight. The reaction was quenched with 20% aqueous Na2S2O3 and stirred for 10 min. EtOAc (100 mL) was added and the phases separated. The organic phase was washed with 20% aqueous Na2S2O3, then water and finally with brine. After drying over Na2SO4, the organic extracts were filtered and concentrated in vacuo. The material was purified using flash chromatography (30% EtOAc:DCM) to afford 1.15 g (68%) of the title compound. 1H NMR (400 MHz, CDCl3) δ 8.07 (s, 1H), 4.73 (br s, 2H), 2.33 (s, 3H).

Provenance & Evidence